The first category of acids is the proton donors or Brønsted acids. In the special case of aqueous solutions, proton donors form the hydronium ion H3O+ and are known as Arrhenius acids. Brønsted and Lowry generalized the Arrhenius theory to include non-aqueous solvents. A Brønsted or Arrhenius acid usually contains a hydrogen atom bonded to a chemical structure that is still energetically favorable after loss of H+.
Aqueous Arrhenius acids have characteristic properties which provide a practical description of an acid. Acids form aqueous solutions with a sour taste, can turn blue litmus red, and react with bases and certain metals (like calcium) to form salts. The word acid is derived from the Latin acidus/acēre meaning sour. An aqueous solution of an acid has a pH less than 7 and is colloquially also referred to as 'acid' (as in 'dissolved in acid'), while the strict definition refers only to the solute. A lower pH means a higher acidity, and thus a higher concentration of positive hydrogen ions in the solution. Chemicals or substances having the property of an acid are said to be acidic.
Common aqueous acids include hydrochloric acid (a solution of hydrogen chloride which is found in gastric acid in the stomach and activates digestive enzymes), acetic acid (vinegar is a dilute aqueous solution of this liquid), sulfuric acid (used in car batteries), and citric acid (found in citrus fruits). As these examples show, acids (in the colloquial sense) can be solutions or pure substances, and can be derived from acids (in the strict sense) that are solids, liquids, or gases. Strong acids and some concentrated weak acids are corrosive, but there are exceptions such as carboranes and boric acid.
The second category of acids are Lewis acids, which form a covalent bond with an electron pair. An example is boron trifluoride (BF3), whose boron atom has a vacant orbital which can form a covalent bond by sharing a lone pair of electrons on an atom in a base, for example the nitrogen atom in ammonia (NH3). Lewis considered this as a generalization of the Brønsted definition, so that an acid is a chemical species that accepts electron pairs either directly or by releasing protons (H+) into the solution, which then accept electron pairs. However, hydrogen chloride, acetic acid, and most other Brønsted-Lowry acids cannot form a covalent bond with an electron pair and are therefore not Lewis acids. Conversely, many Lewis acids are not Arrhenius or Brønsted-Lowry acids. In modern terminology, an acid is implicitly a Brønsted acid and not a Lewis acid, since chemists almost always refer to a Lewis acid explicitly as a Lewis acid.
Modern definitions are concerned with the fundamental chemical reactions common to all acids.
Most acids encountered in everyday life are aqueous solutions, or can be dissolved in water, so the Arrhenius and Brønsted-Lowry definitions are the most relevant.
The Brønsted-Lowry definition is the most widely used definition; unless otherwise specified, acid-base reactions are assumed to involve the transfer of a proton (H+) from an acid to a base.
Hydronium ions are acids according to all three definitions. Although alcohols and amines can be Brønsted-Lowry acids, they can also function as Lewis bases due to the lone pairs of electrons on their oxygen and nitrogen atoms.
The Swedish chemist Svante Arrhenius attributed the properties of acidity to hydrogen ions (H+) or protons in 1884. An Arrhenius acid is a substance that, when added to water, increases the concentration of H+ ions in the water. Note that chemists often write H+(aq) and refer to the hydrogen ion when describing acid-base reactions but the free hydrogen nucleus, a proton, does not exist alone in water, it exists as the hydronium ion, H3O+. Thus, an Arrhenius acid can also be described as a substance that increases the concentration of hydronium ions when added to water. Examples include molecular substances such as HCl and acetic acid.
An Arrhenius base, on the other hand, is a substance which increases the concentration of hydroxide (OH−) ions when dissolved in water. This decreases the concentration of hydronium because the ions react to form H2O molecules:
(aq) + OH−
(aq) ⇌ H2O(l) + H2O(l)
Due to this equilibrium, any increase in the concentration of hydronium is accompanied by a decrease in the concentration of hydroxide. Thus, an Arrhenius acid could also be said to be one that decreases hydroxide concentration, while an Arrhenius base increases it.
In an acidic solution, the concentration of hydronium ions is greater than 10−7 moles per liter. Since pH is defined as the negative logarithm of the concentration of hydronium ions, acidic solutions thus have a pH of less than 7.
While the Arrhenius concept is useful for describing many reactions, it is also quite limited in its scope. In 1923 chemists Johannes Nicolaus Brønsted and Thomas Martin Lowry independently recognized that acid-base reactions involve the transfer of a proton. A Brønsted-Lowry acid (or simply Brønsted acid) is a species that donates a proton to a Brønsted-Lowry base. Brønsted-Lowry acid-base theory has several advantages over Arrhenius theory. Consider the following reactions of acetic acid (CH3COOH), the organic acid that gives vinegar its characteristic taste:
Both theories easily describe the first reaction: CH3COOH acts as an Arrhenius acid because it acts as a source of H3O+ when dissolved in water, and it acts as a Brønsted acid by donating a proton to water. In the second example CH3COOH undergoes the same transformation, in this case donating a proton to ammonia (NH3), but does not relate to the Arrhenius definition of an acid because the reaction does not produce hydronium. Nevertheless, CH3COOH is both an Arrhenius and a Brønsted-Lowry acid.
Brønsted-Lowry theory can be used to describe reactions of molecular compounds in nonaqueous solution or the gas phase. Hydrogen chloride (HCl) and ammonia combine under several different conditions to form ammonium chloride, NH4Cl. In aqueous solution HCl behaves as hydrochloric acid and exists as hydronium and chloride ions. The following reactions illustrate the limitations of Arrhenius's definition:
As with the acetic acid reactions, both definitions work for the first example, where water is the solvent and hydronium ion is formed by the HCl solute. The next two reactions do not involve the formation of ions but are still proton-transfer reactions. In the second reaction hydrogen chloride and ammonia (dissolved in benzene) react to form solid ammonium chloride in a benzene solvent and in the third gaseous HCl and NH3 combine to form the solid.
A third, only marginally related concept was proposed in 1923 by Gilbert N. Lewis, which includes reactions with acid-base characteristics that do not involve a proton transfer. A Lewis acid is a species that accepts a pair of electrons from another species; in other words, it is an electron pair acceptor. Brønsted acid-base reactions are proton transfer reactions while Lewis acid-base reactions are electron pair transfers. Many Lewis acids are not Brønsted-Lowry acids. Contrast how the following reactions are described in terms of acid-base chemistry:
In the first reaction a fluoride ion, F−, gives up an electron pair to boron trifluoride to form the product tetrafluoroborate. Fluoride "loses" a pair of valence electrons because the electrons shared in the B—F bond are located in the region of space between the two atomic nuclei and are therefore more distant from the fluoride nucleus than they are in the lone fluoride ion. BF3 is a Lewis acid because it accepts the electron pair from fluoride. This reaction cannot be described in terms of Brønsted theory because there is no proton transfer. The second reaction can be described using either theory. A proton is transferred from an unspecified Brønsted acid to ammonia, a Brønsted base; alternatively, ammonia acts as a Lewis base and transfers a lone pair of electrons to form a bond with a hydrogen ion. The species that gains the electron pair is the Lewis acid; for example, the oxygen atom in H3O+ gains a pair of electrons when one of the H—O bonds is broken and the electrons shared in the bond become localized on oxygen. Depending on the context, a Lewis acid may also be described as an oxidizer or an electrophile. Organic Brønsted acids, such as acetic, citric, or oxalic acid, are not Lewis acids. They dissociate in water to produce a Lewis acid, H+, but at the same time also yield an equal amount of a Lewis base (acetate, citrate, or oxalate, respectively, for the acids mentioned). Few, if any, of the acids discussed in the following are Lewis acids.
Reactions of acids are often generalized in the form HA ⇌ H+ + A−, where HA represents the acid and A− is the conjugate base. This reaction is referred to as protolysis. The protonated form (HA) of an acid is also sometimes referred to as the free acid.
Acid-base conjugate pairs differ by one proton, and can be interconverted by the addition or removal of a proton (protonation and deprotonation, respectively). Note that the acid can be the charged species and the conjugate base can be neutral in which case the generalized reaction scheme could be written as HA+ ⇌ H+ + A. In solution there exists an equilibrium between the acid and its conjugate base. The equilibrium constant K is an expression of the equilibrium concentrations of the molecules or the ions in solution. Brackets indicate concentration, such that [H2O] means the concentration of H2O. The acid dissociation constant Ka is generally used in the context of acid-base reactions. The numerical value of Ka is equal to the product of the concentrations of the products divided by the concentration of the reactants, where the reactant is the acid (HA) and the products are the conjugate base and H+.
The stronger of two acids will have a higher Ka than the weaker acid; the ratio of hydrogen ions to acid will be higher for the stronger acid as the stronger acid has a greater tendency to lose its proton. Because the range of possible values for Ka spans many orders of magnitude, a more manageable constant, pKa is more frequently used, where pKa = −log10 Ka. Stronger acids have a smaller pKa than weaker acids. Experimentally determined pKa at 25 °C in aqueous solution are often quoted in textbooks and reference material.
In the classical naming system, acids are named according to their anions. That ionic suffix is dropped and replaced with a new suffix (and sometimes prefix), according to the table below. For example, HCl has chloride as its anion, so the -ide suffix makes it take the form hydrochloric acid. In the IUPAC naming system, "aqueous" is simply added to the name of the ionic compound. Thus, for hydrogen chloride, the IUPAC name would be aqueous hydrogen chloride. The prefix "hydro-" is added only if the acid is made up of just hydrogen and one other element.
Classical naming system:
|Anion prefix||Anion suffix||Acid prefix||Acid suffix||Example|
|per||ate||per||ic acid||perchloric acid (HClO4)|
|ate||ic acid||chloric acid (HClO3)|
|ite||ous acid||chlorous acid (HClO2)|
|hypo||ite||hypo||ous acid||hypochlorous acid (HClO)|
|ide||hydro||ic acid||hydrochloric acid (HCl)|
The strength of an acid refers to its ability or tendency to lose a proton. A strong acid is one that completely dissociates in water; in other words, one mole of a strong acid HA dissolves in water yielding one mole of H+ and one mole of the conjugate base, A−, and none of the protonated acid HA. In contrast, a weak acid only partially dissociates and at equilibrium both the acid and the conjugate base are in solution. Examples of strong acids are hydrochloric acid (HCl), hydroiodic acid (HI), hydrobromic acid (HBr), perchloric acid (HClO4), nitric acid (HNO3) and sulfuric acid (H2SO4). In water each of these essentially ionizes 100%. The stronger an acid is, the more easily it loses a proton, H+. Two key factors that contribute to the ease of deprotonation are the polarity of the H—A bond and the size of atom A, which determines the strength of the H—A bond. Acid strengths are also often discussed in terms of the stability of the conjugate base.
Stronger acids have a larger Ka and a more negative pKa than weaker acids.
Sulfonic acids, which are organic oxyacids, are a class of strong acids. A common example is toluenesulfonic acid (tosylic acid). Unlike sulfuric acid itself, sulfonic acids can be solids. In fact, polystyrene functionalized into polystyrene sulfonate is a solid strongly acidic plastic that is filterable.
Superacids are acids stronger than 100% sulfuric acid. Examples of superacids are fluoroantimonic acid, magic acid and perchloric acid. Superacids can permanently protonate water to give ionic, crystalline hydronium "salts". They can also quantitatively stabilize carbocations.
While Ka measures the strength of an acid compound, the strength of an aqueous acid solution is measured by pH, which is an indication of the concentration of hydronium in the solution. The pH of a simple solution of an acid compound in water is determined by the dilution of the compound and the compound's Ka.
Monoprotic acids, also known as monobasic acids, are those acids that are able to donate one proton per molecule during the process of dissociation (sometimes called ionization) as shown below (symbolized by HA):
Common examples of monoprotic acids in mineral acids include hydrochloric acid (HCl) and nitric acid (HNO3). On the other hand, for organic acids the term mainly indicates the presence of one carboxylic acid group and sometimes these acids are known as monocarboxylic acid. Examples in organic acids include formic acid (HCOOH), acetic acid (CH3COOH) and benzoic acid (C6H5COOH).
Polyprotic acids, also known as polybasic acids, are able to donate more than one proton per acid molecule, in contrast to monoprotic acids that only donate one proton per molecule. Specific types of polyprotic acids have more specific names, such as diprotic (or dibasic) acid (two potential protons to donate), and triprotic (or tribasic) acid (three potential protons to donate).
A diprotic acid (here symbolized by H2A) can undergo one or two dissociations depending on the pH. Each dissociation has its own dissociation constant, Ka1 and Ka2.
The first dissociation constant is typically greater than the second; i.e., Ka1 > Ka2. For example, sulfuric acid (H2SO4) can donate one proton to form the bisulfate anion (HSO−
4), for which Ka1 is very large; then it can donate a second proton to form the sulfate anion (SO2−
4), wherein the Ka2 is intermediate strength. The large Ka1 for the first dissociation makes sulfuric a strong acid. In a similar manner, the weak unstable carbonic acid (H2CO3) can lose one proton to form bicarbonate anion (HCO−
3) and lose a second to form carbonate anion (CO2−
3). Both Ka values are small, but Ka1 > Ka2 .
A triprotic acid (H3A) can undergo one, two, or three dissociations and has three dissociation constants, where Ka1 > Ka2 > Ka3.
An inorganic example of a triprotic acid is orthophosphoric acid (H3PO4), usually just called phosphoric acid. All three protons can be successively lost to yield H2PO−
4, then HPO2−
4, and finally PO3−
4, the orthophosphate ion, usually just called phosphate. Even though the positions of the three protons on the original phosphoric acid molecule are equivalent, the successive Ka values differ since it is energetically less favorable to lose a proton if the conjugate base is more negatively charged. An organic example of a triprotic acid is citric acid, which can successively lose three protons to finally form the citrate ion.
Although the subsequent loss of each hydrogen ion is less favorable, all of the conjugate bases are present in solution. The fractional concentration, α (alpha), for each species can be calculated. For example, a generic diprotic acid will generate 3 species in solution: H2A, HA−, and A2−. The fractional concentrations can be calculated as below when given either the pH (which can be converted to the [H+]) or the concentrations of the acid with all its conjugate bases:
A plot of these fractional concentrations against pH, for given K1 and K2, is known as a Bjerrum plot. A pattern is observed in the above equations and can be expanded to the general n -protic acid that has been deprotonated i -times:
where K0 = 1 and the other K-terms are the dissociation constants for the acid.
Neutralization is the basis of titration, where a pH indicator shows equivalence point when the equivalent number of moles of a base have been added to an acid. It is often wrongly assumed that neutralization should result in a solution with pH 7.0, which is only the case with similar acid and base strengths during a reaction.
Neutralization with a base weaker than the acid results in a weakly acidic salt. An example is the weakly acidic ammonium chloride, which is produced from the strong acid hydrogen chloride and the weak base ammonia. Conversely, neutralizing a weak acid with a strong base gives a weakly basic salt, e.g. sodium fluoride from hydrogen fluoride and sodium hydroxide.
In order for a protonated acid to lose a proton, the pH of the system must rise above the pKa of the acid. The decreased concentration of H+ in that basic solution shifts the equilibrium towards the conjugate base form (the deprotonated form of the acid). In lower-pH (more acidic) solutions, there is a high enough H+ concentration in the solution to cause the acid to remain in its protonated form.
Solutions of weak acids and salts of their conjugate bases form buffer solutions.
To determine the concentration of an acid in an aqueous solution, an acid-base titration is commonly performed. A strong base solution with a known concentration, usually NaOH or KOH, is added to neutralize the acid solution according to the color change of the indicator with the amount of base added. The titration curve of an acid titrated by a base has two axes, with the base volume on the x-axis and the solution's pH value on the y-axis. The pH of the solution always goes up as the base is added to the solution.
For each diprotic acid titration curve, from left to right, there are two midpoints, two equivalence points, and two buffer regions.
Due to the successive dissociation processes, there are two equivalence points in the titration curve of a diprotic acid. The first equivalence point occurs when all first hydrogen ions from the first ionization are titrated. In other words, the amount of OH− added equals the original amount of H2A at the first equivalence point. The second equivalence point occurs when all hydrogen ions are titrated. Therefore, the amount of OH− added equals twice the amount of H2A at this time. For a weak diprotic acid titrated by a strong base, the second equivalence point must occur at pH above 7 due to the hydrolysis of the resulted salts in the solution. At either equivalence point, adding a drop of base will cause the steepest rise of the pH value in the system.
A titration curve for a diprotic acid contains two midpoints where pH=pKa. Since there are two different Ka values, the first midpoint occurs at pH=pKa1 and the second one occurs at pH=pKa2. Each segment of the curve which contains a midpoint at its center is called the buffer region. Because the buffer regions consist of the acid and its conjugate base, it can resist pH changes when base is added until the next equivalent points.
Acids exist universally in our life. There are both numerous kinds of natural acid compounds with biological functions and massive synthesized acids which are used in many ways.
Acids are fundamental reagents in treating almost all processes in today's industry. Sulfuric acid, a diprotic acid, is the most widely used acid in industry, which is also the most-produced industrial chemical in the world. It is mainly used in producing fertilizer, detergent, batteries and dyes, as well as used in processing many products such like removing impurities. According to the statistics data in 2011, the annual production of sulfuric acid was around 200 million tonnes in the world. For example, phosphate minerals react with sulfuric acid to produce phosphoric acid for the production of phosphate fertilizers, and zinc is produced by dissolving zinc oxide into sulfuric acid, purifying the solution and electrowinning.
In the chemical industry, acids react in neutralization reactions to produce salts. For example, nitric acid reacts with ammonia to produce ammonium nitrate, a fertilizer. Additionally, carboxylic acids can be esterified with alcohols, to produce esters.
Tartaric acid is an important component of some commonly used foods like unripened mangoes and tamarind. Natural fruits and vegetables also contain acids. Citric acid is present in oranges, lemon and other citrus fruits. Oxalic acid is present in tomatoes, spinach, and especially in carambola and rhubarb; rhubarb leaves and unripe carambolas are toxic because of high concentrations of oxalic acid. Ascorbic acid (Vitamin C) is an essential vitamin for the human body and is present in such foods as amla (Indian gooseberry), lemon, citrus fruits, and guava.
Many acids can be found in various kinds of food as additives, as they alter their taste and serve as preservatives. Phosphoric acid, for example, is a component of cola drinks. Acetic acid is used in day-to-day life as vinegar. Citric acid is used as a preservative in sauces and pickles.
Carbonic acid is one of the most common acid additive that is widely added in soft drinks, such as Coca-Cola. During the manufacturing process of soft drinks, CO2 is usually pressurized to dissolve in these drinks to generate carbonic acid. Carbonic acid is very unstable and tend to decompose into water and CO2 in normal temperature and pressure. Therefore, when we open the bottles or cans of these kinds of soft drinks, CO2 bubbles come out and thus we feel 'sparks'.
Certain acids are used as drugs. Acetylsalicylic acid (Aspirin) is used as a pain killer and for bringing down fevers.
Acids play important roles in the human body. The hydrochloric acid present in the stomach aids digestion by breaking down large and complex food molecules. Amino acids are required for synthesis of proteins required for growth and repair of body tissues. Fatty acids are also required for growth and repair of body tissues. Nucleic acids are important for the manufacturing of DNA and RNA and transmitting of traits to offspring through genes. Carbonic acid is important for maintenance of pH equilibrium in the body.
Human bodies contain a variety of organic and inorganic compounds, among those dicarboxylic acids play an essential role in many biological behaviors. Many of those acids are amino acids which mainly serve as materials for the synthesis of proteins. Other weak acids serve as buffers with their conjugate bases to keep the body's pH from undergoing large scale changes which would be harmful to cells. The rest of the dicarboxylic acids also participate in the synthesis of various biologically important compounds in human bodies.
Acids are used as catalysts in industrial and organic chemistry; for example, sulfuric acid is used in very large quantities in the alkylation process to produce gasoline. Some acids, such as sulfuric, phosphoric, and hydrochloric acids, also effect dehydration and condensation reactions. In biochemistry, many enzymes employ acid catalysis.
Many biologically important molecules are acids. Nucleic acids, which contain acidic phosphate groups, include DNA and RNA. Nucleic acids contain the genetic code that determines many of an organism's characteristics, and is passed from parents to offspring. DNA contains the chemical blueprint for the synthesis of proteins which are made up of amino acid subunits. Cell membranes contain fatty acid esters such as phospholipids.
An α-amino acid has a central carbon (the α or alpha carbon) which is covalently bonded to a carboxyl group (thus they are carboxylic acids), an amino group, a hydrogen atom and a variable group. The variable group, also called the R group or side chain, determines the identity and many of the properties of a specific amino acid. In glycine, the simplest amino acid, the R group is a hydrogen atom, but in all other amino acids it is contains one or more carbon atoms bonded to hydrogens, and may contain other elements such as sulfur, oxygen or nitrogen. With the exception of glycine, naturally occurring amino acids are chiral and almost invariably occur in the L-configuration. Peptidoglycan, found in some bacterial cell walls contains some D-amino acids. At physiological pH, typically around 7, free amino acids exist in a charged form, where the acidic carboxyl group (-COOH) loses a proton (-COO−) and the basic amine group (-NH2) gains a proton (-NH+
3). The entire molecule has a net neutral charge and is a zwitterion, with the exception of amino acids with basic or acidic side chains. Aspartic acid, for example, possesses one protonated amine and two deprotonated carboxyl groups, for a net charge of −1 at physiological pH.
Fatty acids and fatty acid derivatives are another group of carboxylic acids that play a significant role in biology. These contain long hydrocarbon chains and a carboxylic acid group on one end. The cell membrane of nearly all organisms is primarily made up of a phospholipid bilayer, a micelle of hydrophobic fatty acid esters with polar, hydrophilic phosphate "head" groups. Membranes contain additional components, some of which can participate in acid-base reactions.
In humans and many other animals, hydrochloric acid is a part of the gastric acid secreted within the stomach to help hydrolyze proteins and polysaccharides, as well as converting the inactive pro-enzyme, pepsinogen into the enzyme, pepsin. Some organisms produce acids for defense; for example, ants produce formic acid.
Acid-base equilibrium plays a critical role in regulating mammalian breathing. Oxygen gas (O2) drives cellular respiration, the process by which animals release the chemical potential energy stored in food, producing carbon dioxide (CO2) as a byproduct. Oxygen and carbon dioxide are exchanged in the lungs, and the body responds to changing energy demands by adjusting the rate of ventilation. For example, during periods of exertion the body rapidly breaks down stored carbohydrates and fat, releasing CO2 into the blood stream. In aqueous solutions such as blood CO2 exists in equilibrium with carbonic acid and bicarbonate ion.
It is the decrease in pH that signals the brain to breathe faster and deeper, expelling the excess CO2 and resupplying the cells with O2.
Cell membranes are generally impermeable to charged or large, polar molecules because of the lipophilic fatty acyl chains comprising their interior. Many biologically important molecules, including a number of pharmaceutical agents, are organic weak acids which can cross the membrane in their protonated, uncharged form but not in their charged form (i.e. as the conjugate base). For this reason the activity of many drugs can be enhanced or inhibited by the use of antacids or acidic foods. The charged form, however, is often more soluble in blood and cytosol, both aqueous environments. When the extracellular environment is more acidic than the neutral pH within the cell, certain acids will exist in their neutral form and will be membrane soluble, allowing them to cross the phospholipid bilayer. Acids that lose a proton at the intracellular pH will exist in their soluble, charged form and are thus able to diffuse through the cytosol to their target. Ibuprofen, aspirin and penicillin are examples of drugs that are weak acids.
A sulfonic acid has the general formula RS(=O)2–OH, where R is an organic radical.
Halogenation at alpha position increases acid strength, so that the following acids are all stronger than acetic acid.
Normal carboxylic acids are the direct union of a carbonyl group and a hydroxyl group. In vinylogous carboxylic acids, a carbon-carbon double bond separates the carbonyl and hydroxyl groups.
Acetic acid , systematically named ethanoic acid , is a colourless liquid organic compound with the chemical formula CH3COOH (also written as CH3CO2H or C2H4O2). When undiluted, it is sometimes called glacial acetic acid. Vinegar is no less than 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. Acetic acid has a distinctive sour taste and pungent smell. In addition to household vinegar, it is mainly produced as a precursor to polyvinyl acetate and cellulose acetate. It is classified as a weak acid since it only partially dissociates in solution, but concentrated acetic acid is corrosive and can attack the skin.
Acetic acid is the second simplest carboxylic acid (after formic acid). It consists of a methyl group attached to a carboxyl group. It is an important chemical reagent and industrial chemical, used primarily in the production of cellulose acetate for photographic film, polyvinyl acetate for wood glue, and synthetic fibres and fabrics. In households, diluted acetic acid is often used in descaling agents. In the food industry, acetic acid is controlled by the food additive code E260 as an acidity regulator and as a condiment. In biochemistry, the acetyl group, derived from acetic acid, is fundamental to all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.
The global demand for acetic acid is about 6.5 million metric tons per year (Mt/a), of which approximately 1.5 Mt/a is met by recycling; the remainder is manufactured from methanol. Vinegar is mostly dilute acetic acid, often produced by fermentation and subsequent oxidation of ethanol.Acid rain
Acid rain is a rain or any other form of precipitation that is unusually acidic, meaning that it has elevated levels of hydrogen ions (low pH). It can have harmful effects on plants, aquatic animals and infrastructure. Acid rain is caused by emissions of sulfur dioxide and nitrogen oxide, which react with the water molecules in the atmosphere to produce acids. Some governments have made efforts since the 1970s to reduce the release of sulfur dioxide and nitrogen oxide into the atmosphere with positive results. Nitrogen oxides can also be produced naturally by lightning strikes, and sulfur dioxide is produced by volcanic eruptions. Acid rain has been shown to have adverse impacts on forests, freshwaters and soils, killing insect and aquatic life-forms, causing paint to peel, corrosion of steel structures such as bridges, and weathering of stone buildings and statues as well as having impacts on human health.Amino acid
Amino acids are organic compounds containing amine (-NH2) and carboxyl (-COOH) functional groups, along with a side chain (R group) specific to each amino acid. The key elements of an amino acid are carbon (C), hydrogen (H), oxygen (O), and nitrogen (N), although other elements are found in the side chains of certain amino acids. About 500 naturally occurring amino acids are known (though only 20 appear in the genetic code) and can be classified in many ways. They can be classified according to the core structural functional groups' locations as alpha- (α-), beta- (β-), gamma- (γ-) or delta- (δ-) amino acids; other categories relate to polarity, pH level, and side chain group type (aliphatic, acyclic, aromatic, containing hydroxyl or sulfur, etc.). In the form of proteins, amino acid residues form the second-largest component (water is the largest) of human muscles and other tissues. Beyond their role as residues in proteins, amino acids participate in a number of processes such as neurotransmitter transport and biosynthesis.
In biochemistry, amino acids having both the amine and the carboxylic acid groups attached to the first (alpha-) carbon atom have particular importance. They are known as 2-, alpha-, or α-amino acids (generic formula H2NCHRCOOH in most cases, where R is an organic substituent known as a "side chain"); often the term "amino acid" is used to refer specifically to these. They include the 22 proteinogenic ("protein-building") amino acids, which combine into peptide chains ("polypeptides") to form the building-blocks of a vast array of proteins. These are all L-stereoisomers ("left-handed" isomers), although a few D-amino acids ("right-handed") occur in bacterial envelopes, as a neuromodulator (D-serine), and in some antibiotics.Twenty of the proteinogenic amino acids are encoded directly by triplet codons in the genetic code and are known as "standard" amino acids. The other two ("non-standard" or "non-canonical") are selenocysteine (present in many prokaryotes as well as most eukaryotes, but not coded directly by DNA), and pyrrolysine (found only in some archea and one bacterium). Pyrrolysine and selenocysteine are encoded via variant codons; for example, selenocysteine is encoded by stop codon and SECIS element. N-formylmethionine (which is often the initial amino acid of proteins in bacteria, mitochondria, and chloroplasts) is generally considered as a form of methionine rather than as a separate proteinogenic amino acid. Codon–tRNA combinations not found in nature can also be used to "expand" the genetic code and form novel proteins known as alloproteins incorporating non-proteinogenic amino acids.Many important proteinogenic and non-proteinogenic amino acids have biological functions. For example, in the human brain, glutamate (standard glutamic acid) and gamma-amino-butyric acid ("GABA", non-standard gamma-amino acid) are, respectively, the main excitatory and inhibitory neurotransmitters. Hydroxyproline, a major component of the connective tissue collagen, is synthesised from proline. Glycine is a biosynthetic precursor to porphyrins used in red blood cells. Carnitine is used in lipid transport.
Nine proteinogenic amino acids are called "essential" for humans because they cannot be produced from other compounds by the human body and so must be taken in as food. Others may be conditionally essential for certain ages or medical conditions. Essential amino acids may also differ between species.Because of their biological significance, amino acids are important in nutrition and are commonly used in nutritional supplements, fertilizers, feed, and food technology. Industrial uses include the production of drugs, biodegradable plastics, and chiral catalysts.Aspirin
Aspirin, also known as acetylsalicylic acid (ASA), is a medication used to treat pain, fever, or inflammation. Specific inflammatory conditions which aspirin is used to treat include Kawasaki disease, pericarditis, and rheumatic fever. Aspirin given shortly after a heart attack decreases the risk of death. Aspirin is also used long-term to help prevent further heart attacks, ischaemic strokes, and blood clots in people at high risk. It may also decrease the risk of certain types of cancer, particularly colorectal cancer. For pain or fever, effects typically begin within 30 minutes. Aspirin is a nonsteroidal anti-inflammatory drug (NSAID) and works similarly to other NSAIDs but also suppresses the normal functioning of platelets.One common adverse effect is an upset stomach. More significant side effects include stomach ulcers, stomach bleeding, and worsening asthma. Bleeding risk is greater among those who are older, drink alcohol, take other NSAIDs, or are on other blood thinners. Aspirin is not recommended in the last part of pregnancy. It is not generally recommended in children with infections because of the risk of Reye syndrome. High doses may result in ringing in the ears.A precursor to aspirin found in leaves from the willow tree has been used for its health effects for at least 2,400 years. In 1853, chemist Charles Frédéric Gerhardt treated the medicine sodium salicylate with acetyl chloride to produce acetylsalicylic acid for the first time. For the next fifty years, other chemists established the chemical structure and came up with more efficient production methods. In 1897, scientists at the Bayer company began studying acetylsalicylic acid as a less-irritating replacement medication for common salicylate medicines. By 1899, Bayer had named it "Aspirin" and sold it around the world. Aspirin's popularity grew over the first half of the twentieth century leading to competition between many brands and formulations. The word Aspirin was Bayer's brand name; however, their rights to the trademark were lost or sold in many countries.Aspirin is one of the most widely used medications globally, with an estimated 40,000 tonnes (44,000 tons) (50 to 120 billion pills) consumed each year. It is on the World Health Organization's (WHO's) List of Essential Medicines, which lists the safest and most effective medicines needed in a health system. As of 2014, the wholesale cost in the developing world is $0.002 to $0.025 USD per dose. As of 2015, the cost for a typical month of medication in the United States is less than US$25.00. It is available as a generic medication. In 2016, it was the 38th most prescribed medication in the United States, with more than 19 million prescriptions.Barbiturate
A barbiturate is a drug that acts as a central nervous system depressant, and can therefore produce a wide spectrum of effects, from mild sedation to death. Barbiturates are effective as anxiolytics, hypnotics, and anticonvulsants, but have physical and psychological addiction potential. They have largely been replaced by benzodiazepines in routine medical practice, particularly in the treatment of anxiety and insomnia, due to the significantly lower risk of addiction and overdose and the lack of an antidote for barbiturate overdose. Despite this, barbiturates are still in use for various purposes: in general anesthesia, epilepsy, treatment of acute migraines or cluster headaches, euthanasia, capital punishment, and assisted suicide.The name barbiturate originates from the fact that they are all chemical derivatives of barbituric acid.Carboxylic acid
A carboxylic acid is an organic compound that contains a carboxyl group (C(=O)OH). The general formula of a carboxylic acid is R–COOH, with R referring to the rest of the (possibly quite large) molecule. Carboxylic acids occur widely. Important examples include the amino acids (which make up proteins) and acetic acid (which is part of vinegar). Deprotonation of a carboxyl group gives a carboxylate anion. Important carboxylate salts are soaps.Citric acid
Citric acid is a weak organic acid that has the chemical formula C6H8O7. It occurs naturally in citrus fruits. In biochemistry, it is an intermediate in the citric acid cycle, which occurs in the metabolism of all aerobic organisms.
More than a million tons of citric acid are manufactured every year. It is used widely as an acidifier, as a flavoring and chelating agent.A citrate is a derivative of citric acid; that is, the salts, esters, and the polyatomic anion found in solution. An example of the former, a salt is trisodium citrate; an ester is triethyl citrate. When part of a salt, the formula of the citrate ion is written as C6H5O3−7 or C3H5O(COO)3−3.Citric acid cycle
The citric acid cycle (CAC) – also known as the TCA cycle (tricarboxylic acid cycle) or the Krebs cycle – is a series of chemical reactions used by all aerobic organisms to release stored energy through the oxidation of acetyl-CoA derived from carbohydrates, fats, and proteins, into adenosine triphosphate (ATP) and carbon dioxide. In addition, the cycle provides precursors of certain amino acids, as well as the reducing agent NADH, that are used in numerous other reactions. Its central importance to many biochemical pathways suggests that it was one of the earliest established components of cellular metabolism and may have originated abiogenically. Even though it is branded as a 'cycle', it is not necessary for metabolites to follow only one specific route; at least three segments of the citric acid cycle have been recognized.The name of this metabolic pathway is derived from the citric acid (a type of tricarboxylic acid, often called citrate, as the ionized form predominates at biological pH) that is consumed and then regenerated by this sequence of reactions to complete the cycle. The cycle consumes acetate (in the form of acetyl-CoA) and water, reduces NAD+ to NADH, and produces carbon dioxide as a waste byproduct. The NADH generated by the citric acid cycle is fed into the oxidative phosphorylation (electron transport) pathway. The net result of these two closely linked pathways is the oxidation of nutrients to produce usable chemical energy in the form of ATP.
In eukaryotic cells, the citric acid cycle occurs in the matrix of the mitochondrion. In prokaryotic cells, such as bacteria, which lack mitochondria, the citric acid cycle reaction sequence is performed in the cytosol with the proton gradient for ATP production being across the cell's surface (plasma membrane) rather than the inner membrane of the mitochondrion. The overall yield of energy-containing compounds from the TCA cycle is three NADH, one FADH2, and one GTP.DNA
Deoxyribonucleic acid ( (listen); DNA) is a molecule composed of two chains that coil around each other to form a double helix carrying the genetic instructions used in the growth, development, functioning, and reproduction of all known organisms and many viruses. DNA and ribonucleic acid (RNA) are nucleic acids; alongside proteins, lipids and complex carbohydrates (polysaccharides), nucleic acids are one of the four major types of macromolecules that are essential for all known forms of life.
The two DNA strands are also known as polynucleotides as they are composed of simpler monomeric units called nucleotides. Each nucleotide is composed of one of four nitrogen-containing nucleobases (cytosine [C], guanine [G], adenine [A] or thymine [T]), a sugar called deoxyribose, and a phosphate group. The nucleotides are joined to one another in a chain by covalent bonds between the sugar of one nucleotide and the phosphate of the next, resulting in an alternating sugar-phosphate backbone. The nitrogenous bases of the two separate polynucleotide strands are bound together, according to base pairing rules (A with T and C with G), with hydrogen bonds to make double-stranded DNA.
The complementary nitrogenous bases are divided into two groups, pyrimidines and purines. In DNA, the pyrimidines are thymine and cytosine; the purines are adenine and guanine.
Both strands of double-stranded DNA store the same biological information. This information is replicated as and when the two strands separate. A large part of DNA (more than 98% for humans) is non-coding, meaning that these sections do not serve as patterns for protein sequences.
The two strands of DNA run in opposite directions to each other and are thus antiparallel. Attached to each sugar is one of four types of nucleobases (informally, bases). It is the sequence of these four nucleobases along the backbone that encodes genetic information. RNA strands are created using DNA strands as a template in a process called transcription. Under the genetic code, these RNA strands specify the sequence of amino acids within proteins in a process called translation.
Within eukaryotic cells, DNA is organized into long structures called chromosomes. Before typical cell division, these chromosomes are duplicated in the process of DNA replication, providing a complete set of chromosomes for each daughter cell. Eukaryotic organisms (animals, plants, fungi and protists) store most of their DNA inside the cell nucleus as nuclear DNA, and some in the mitochondria as mitochondrial DNA, or in chloroplasts as chloroplast DNA. In contrast, prokaryotes (bacteria and archaea) store their DNA only in the cytoplasm, in circular chromosomes. Within eukaryotic chromosomes, chromatin proteins, such as histones, compact and organize DNA. These compact structures guide the interactions between DNA and other proteins, helping control which parts of the DNA are transcribed.
DNA was first isolated by Friedrich Miescher in 1869. Its molecular structure was first identified by Francis Crick and James Watson at the Cavendish Laboratory within the University of Cambridge in 1953, whose model-building efforts were guided by X-ray diffraction data acquired by Raymond Gosling, who was a post-graduate student of Rosalind Franklin. DNA is used by researchers as a molecular tool to explore physical laws and theories, such as the ergodic theorem and the theory of elasticity. The unique material properties of DNA have made it an attractive molecule for material scientists and engineers interested in micro- and nano-fabrication. Among notable advances in this field are DNA origami and DNA-based hybrid materials.Fatty acid
In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with a long aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, from 4 to 28. Fatty acids are usually not found in organisms, but instead as three main classes of esters: triglycerides, phospholipids, and cholesterol esters. In any of these forms, fatty acids are both important dietary sources of fuel for animals and they are important structural components for cells.Folate
Folate, distinct forms of which are known as folic acid, folacin, and vitamin B9, is one of the B vitamins. It may be taken by mouth or by injection. The recommended adult daily intake of folate in the U.S. is 400 micrograms from foods or dietary supplements. Folate in the form of folic acid is used to treat anemia caused by folic acid deficiency. Folic acid is also used as a supplement by women during pregnancy to reduce the risk of neural tube defects (NTDs) in the baby. Low levels in early pregnancy are believed to be the cause of more than half of babies born with NTDs. More than 80 countries use fortification of certain foods with folic acid as a measure to decrease the rate of NTDs. Long-term supplementation is also associated with small reductions in the risk of stroke and cardiovascular disease.No common side effects are known. There are concerns that large amounts of folic acid might hide vitamin B12 deficiency. Folate is essential for the body to make DNA, RNA, and metabolise amino acids, which are required for cell division. As humans cannot make folate, it is required from the diet, making it an essential vitamin.Not consuming enough folate can lead to folate deficiency. This may result in a type of anemia in which low numbers of large red blood cells occur. Symptoms may include feeling tired, heart palpitations, shortness of breath, open sores on the tongue, and changes in the color of the skin or hair. Folate deficiency in children may develop within a month of poor dietary intake. In adults, normal total body folate is between 10 and 30 mg with blood levels of greater than 7 nmol/L (3 ng/mL).Folic acid was discovered between 1931 and 1943. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. The wholesale cost of supplements in the developing world is between US$0.001 and 0.005 per dose as of 2014. The term "folic" is from the Latin word folium (which means leaf) because it was found in dark-green leafy vegetables. Folates occur naturally in many foods. In 2016 it was the 96th most prescribed medication in the United States with more than 8 million prescriptions.Hydrochloric acid
Hydrochloric acid or muriatic acid is a colorless inorganic chemical system with the formula H2O:HCl. Hydrochloric acid has a distinctive pungent smell. It is classified as strongly acidic and can attack the skin over a wide composition range, since the hydrogen chloride completely dissociates in aqueous solution.
Hydrochloric acid is the simplest chlorine-based acid system containing water. It is a solution of hydrogen chloride and water, and a variety of other chemical species, including hydronium and chloride ions. It is an important chemical reagent and industrial chemical, used in the production of polyvinyl chloride for plastic. In households, diluted hydrochloric acid is often used as a descaling agent. In the food industry, hydrochloric acid is used as a food additive and in the production of gelatin. Hydrochloric acid is also used in leather processing.
Hydrochloric acid was discovered by the alchemist Jabir ibn Hayyan around the year 800 AD. It was historically called acidum salis and spirits of salt because it was produced from rock salt and "green vitriol" (Iron(II) sulfate) (by Basilius Valentinus in the 15th century) and later from the chemically similar common salt and sulfuric acid (by Johann Rudolph Glauber in the 17th century). Free hydrochloric acid was first formally described in the 16th century by Libavius. Later, it was used by chemists such as Glauber, Priestley, and Davy in their scientific research. Unless pressurized or cooled, hydrochloric acid will turn into a gas if there is around 60% or less of water. Hydrochloric acid is also known as hydronium chloride, in contrast to its anhydrous parent known as hydrogen chloride, or dry HCl.Lysergic acid diethylamide
Lysergic acid diethylamide (LSD), also known as acid, is a hallucinogenic drug. (The abbreviation LSD comes from the german name of the molecule: Lysergsäurediethylamid.)
Effects typically include altered thoughts, feelings, and awareness of one's surroundings. Many users see or hear things that do not exist. Dilated pupils, increased blood pressure, and increased body temperature are typical. Effects typically begin within half an hour and can last for up to 12 hours. It is used mainly as a recreational drug and for spiritual reasons.While LSD does not appear to be addictive, tolerance with use of increasing doses may occur. Adverse psychiatric reactions such as anxiety, paranoia, and delusions are possible. Distressing flashbacks, a condition called hallucinogen persisting perception disorder, may occur despite no further use. Death as a result of LSD, though occasionally occurring in accidents, is very rare. The effects of LSD are believed to occur as a result of alterations in the serotonin system. As little as 20 micrograms can produce an effect. In pure form LSD is clear or white in color, has no smell, and is crystalline. It breaks down with exposure to ultraviolet light.In the United States, as of 2017, about 10% of people have used LSD at some point in their lives, while 0.7% have used it in the last year. It was most popular in the 1960s to 1980s. LSD is typically either swallowed or held under the tongue. It is most often sold on blotter paper and less commonly as tablets or in gelatin squares. There are no known treatments for addiction, if it occurs.LSD was first made by Albert Hofmann in 1938 from lysergic acid, a chemical from the fungus ergot. Hofmann discovered its hallucinogenic properties in 1943. In the 1950s, the Central Intelligence Agency (CIA) believed the drug might be useful for mind control so tested it on people, some without their knowledge, in a program called MKUltra. LSD was sold as a medication for research purposes under the trade-name Delysid in the 1950s and 1960s. It was listed as a schedule 1 controlled substance by the United Nations in 1971. It currently has no approved medical use. In Europe, as of 2011, the typical cost of a dose was between €4.50 and €25.Nitric acid
Nitric acid (HNO3), also known as aqua fortis (Latin for "strong water") and spirit of niter, is a highly corrosive mineral acid.
The pure compound is colorless, but older samples tend to acquire a yellow cast due to decomposition into oxides of nitrogen and water. Most commercially available nitric acid has a concentration of 68% in water. When the solution contains more than 86% HNO3, it is referred to as fuming nitric acid. Depending on the amount of nitrogen dioxide present, fuming nitric acid is further characterized as white fuming nitric acid at concentrations above 95%, or red fuming nitric acid at concentrations above 86%.
Nitric acid is the primary reagent used for nitration – the addition of a nitro group, typically to an organic molecule. While some resulting nitro compounds are shock- and thermally-sensitive explosives, a few are stable enough to be used in munitions and demolition, while others are still more stable and used as pigments in inks and dyes. Nitric acid is also commonly used as a strong oxidizing agent.PH
In chemistry, pH () is a scale used to specify how acidic or basic a water-based solution is. Acidic solutions have a lower pH, basic solutions have a higher pH. At room temperature, pure water is neither acidic nor basic and has a pH of 7.
The scale is logarithmic. It is approximately the negative of the base 10 logarithm of the molar concentration (measured in units of moles per liter) of hydrogen ions. More precisely it is the negative of the base 10 logarithm of the activity of the hydrogen ion. At 25 °C, solutions with a pH less than 7 are acidic and solutions with a pH greater than 7 are basic. The neutral value of the pH depends on the temperature, being lower than 7 if the temperature increases. Pure water is neutral (pH 7) at 25 °C. Contrary to popular belief, the pH value can be less than 0 or greater than 14 for very strong acids and bases respectively.Measurements of pH are important in agronomy, medicine, chemistry, water treatment, and many other applications.
The pH scale is traceable to a set of standard solutions whose pH is established by international agreement.
Primary pH standard values are determined using a concentration cell with transference, by measuring the potential difference between a hydrogen electrode and a standard electrode such as the silver chloride electrode.
The pH of aqueous solutions can be measured with a glass electrode and a pH meter, or an indicator.
There are three current theories used to describe acid–base reactions: Arrhenius, Bronsted-Lowry and Lewis when determining pH.RNA
Ribonucleic acid (RNA) is a polymeric molecule essential in various biological roles in coding, decoding, regulation and expression of genes. RNA and DNA are nucleic acids, and, along with lipids, proteins and carbohydrates, constitute the four major macromolecules essential for all known forms of life. Like DNA, RNA is assembled as a chain of nucleotides, but unlike DNA it is more often found in nature as a single-strand folded onto itself, rather than a paired double-strand. Cellular organisms use messenger RNA (mRNA) to convey genetic information (using the nitrogenous bases of guanine, uracil, adenine, and cytosine, denoted by the letters G, U, A, and C) that directs synthesis of specific proteins. Many viruses encode their genetic information using an RNA genome.
Some RNA molecules play an active role within cells by catalyzing biological reactions, controlling gene expression, or sensing and communicating responses to cellular signals. One of these active processes is protein synthesis, a universal function in which RNA molecules direct the assembly of proteins on ribosomes. This process uses transfer RNA (tRNA) molecules to deliver amino acids to the ribosome, where ribosomal RNA (rRNA) then links amino acids together to form proteins.Salicylic acid
Salicylic acid (from Latin salix, willow tree) is a lipophilic monohydroxybenzoic acid, a type of phenolic acid, and a beta hydroxy acid (BHA). It has the formula C7H6O3. This colorless crystalline organic acid is widely used in organic synthesis and functions as a plant hormone. It is derived from the metabolism of salicin. In addition to serving as an important active metabolite of aspirin (acetylsalicylic acid), which acts in part as a prodrug to salicylic acid, it is probably best known for its use as a key ingredient in topical anti-acne products. The salts and esters of salicylic acid are known as salicylates.
It is on the WHO Model List of Essential Medicines, the most important medications needed in a basic health system.Sulfuric acid
Sulfuric acid (alternative spelling sulphuric acid), also known as vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with molecular formula H2SO4. It is a colorless, odorless, and syrupy liquid that is soluble in water, in a reaction that is highly exothermic.Its corrosiveness can be mainly ascribed to its strong acidic nature, and, if at a high concentration, its dehydrating and oxidizing properties. It is also hygroscopic, readily absorbing water vapor from the air. Upon contact, sulfuric acid can cause severe chemical burns and even secondary thermal burns; it is very dangerous even at moderate concentrations.Sulfuric acid is a very important commodity chemical, and a nation's sulfuric acid production is a good indicator of its industrial strength. It is widely produced with different methods, such as contact process, wet sulfuric acid process, lead chamber process and some other methods.Sulfuric acid is also a key substance in the chemical industry. It is most commonly used in fertilizer manufacture, but is also important in mineral processing, oil refining, wastewater processing, and chemical synthesis. It has a wide range of end applications including in domestic acidic drain cleaners, as an electrolyte in lead-acid batteries, and in various cleaning agents.Vitamin C
Vitamin C, also known as ascorbic acid and L-ascorbic acid, is a vitamin found in various foods and sold as a dietary supplement. It is used to prevent and treat scurvy. Vitamin C is an essential nutrient involved in the repair of tissue and the enzymatic production of certain neurotransmitters. It is required for the functioning of several enzymes and is important for immune system function. It also functions as an antioxidant.Evidence does not support use in the general population for the prevention of the common cold. There is, however, some evidence that regular use may shorten the length of colds. It is unclear whether supplementation affects the risk of cancer, cardiovascular disease, or dementia. It may be taken by mouth or by injection.Vitamin C is generally well tolerated. Large doses may cause gastrointestinal discomfort, headache, trouble sleeping, and flushing of the skin. Normal doses are safe during pregnancy. The United States Institute of Medicine recommends against taking large doses.Vitamin C was discovered in 1912, isolated in 1928, and in 1933 was the first vitamin to be chemically produced. It is on the World Health Organization Model List of Essential Medicines, the most effective and safe medicines needed in a health system. Vitamin C is available as an inexpensive generic medication and over-the-counter drug. Partly for its discovery, Albert Szent-Györgyi and Walter Norman Haworth were awarded the 1937 Nobel Prizes in Physiology and Medicine and Chemistry, respectively. Foods containing vitamin C include citrus fruits, kiwifruit, broccoli, Brussels sprouts, raw bell peppers, and strawberries. Prolonged storage or cooking may reduce vitamin C content in foods.