Acetone

Acetone, or propanone, is the organic compound with the formula (CH3)2CO.[15] It is a colorless, volatile, flammable liquid and is the simplest and smallest ketone.

Acetone is miscible with water and serves as an important solvent in its own right, typically for cleaning purposes in laboratories. About 6.7 million tonnes were produced worldwide in 2010, mainly for use as a solvent and production of methyl methacrylate and bisphenol A.[16][17] It is a common building block in organic chemistry. Familiar household uses of acetone are as the active ingredient in nail polish remover and as paint thinner.

Acetone is produced and disposed of in the human body through normal metabolic processes. It is normally present in blood and urine. People with diabetes produce it in larger amounts. Reproductive toxicity tests show that it has low potential to cause reproductive problems. Ketogenic diets that increase ketones (acetone, β-hydroxybutyric acid and acetoacetic acid) in the blood are used to counter epileptic attacks in infants and children who suffer from recalcitrant refractory epilepsy.

Acetone[1]
Full structural formula of acetone with dimensions
Skeletal formula of acetone
Ball-and-stick model of acetone
Space-filling model of acetone
Sample of acetone
Names
Preferred IUPAC name
Propan-2-one[7]
Other names
  • Acetone
  • Dimethyl ketone[2]
  • Dimethyl carbonyl
  • β-Ketopropane[2]
  • Propanone[3]
  • 2-Propanone[2]
  • Dimethyl formaldehyde[4]
  • Pyroacetic spirit (archaic)[5]
  • Ketone propane[6]
Identifiers
3D model (JSmol)
3DMet B00058
635680
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.602
EC Number 200-662-2
1466
KEGG
MeSH Acetone
RTECS number AL3150000
UNII
UN number 1090
Properties
C3H6O
Molar mass 58.080 g·mol−1
Appearance Colorless liquid
Odor Pungent, irritating, floral, cucumber like
Density 0.7845 g/cm3 (25 °C)
Melting point −94.7 °C (−138.5 °F; 178.5 K)[12]
Boiling point 56.05 °C (132.89 °F; 329.20 K)[12]
Miscible
Solubility Miscible in benzene, diethyl ether, methanol, chloroform, ethanol[8]
log P -0.16[9]
Vapor pressure
  • 9.39 kPa (0 °C)
  • 30.6 kPa (25 °C)
  • 374 kPa (100 °C)
  • 2.8 MPa (200 °C)[2]
Acidity (pKa)
−33.78·10−6 cm3/mol
1.3588 (VD = 54.46)
Viscosity 0.295 mPa·s (25 °C)[8]
Structure
Trigonal planar at C2
Dihedral at C2
2.91 D
Thermochemistry
125.45 J/(mol·K)
200.4 J/(mol·K)
(−250.03)  (−248.77) kJ/mol
−1.772 MJ/mol
Hazards
Safety data sheet See: data page
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H225, H319, H336, H373
P210, P235, P260, P305+351+338
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasolineHealth code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
3
1
0
Flash point −20 °C (−4 °F; 253 K)
465 °C (869 °F; 738 K)
Explosive limits 2.6–12.8%[13]
1185 mg/m3 (TWA), 2375 mg/m3 (STEL)
Lethal dose or concentration (LD, LC):
  • 5800 mg/kg (rat, oral)
  • 3000 mg/kg (mouse, oral)
  • 5340 mg/kg (rabbit, oral)[14]
20,702 ppm (rat, 8 h)[14]
45,455 ppm (mouse, 1 h)[14]
US health exposure limits (NIOSH):
PEL (Permissible)
1000 ppm (2400 mg/m3)[6]
REL (Recommended)
TWA 250 ppm (590 mg/m3)[6]
IDLH (Immediate danger)
2500 ppm[6]
Related compounds
Related compounds
Supplementary data page
Refractive index (n),
Dielectric constantr), etc.
Thermodynamic
data
Phase behaviour
solid–liquid–gas
UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

History

Acetone was first produced by alchemists during the late Middle Ages via the dry distillation of metal acetates (e.g., lead acetate, which produced "spirit of Saturn" (since the alchemical symbol for lead was also the astrological symbol for the planet Saturn)).[18]

In 1832, French chemist Jean-Baptiste Dumas and German chemist Justus von Liebig determined the empirical formula for acetone.[19][20] In 1833, the French chemist Antoine Bussy named acetone by adding the suffix -one to the stem of the corresponding acid (viz, acetic acid).[21] By 1852, English chemist Alexander William Williamson realized that acetone was methyl acetyl;[22] the following year, the French chemist Charles Frédéric Gerhardt concurred.[23] In 1865, the German chemist August Kekulé published the modern structural formula for acetone.[24][25] Johann Josef Loschmidt had presented the structure of acetone in 1861,[26] but his privately published booklet received little attention. During World War I, Chaim Weizmann developed the process for industrial production of acetone (Weizmann Process).[27]

Metabolism

Biosynthesis

Small amounts of acetone are produced in the body by the decarboxylation of ketone bodies. Certain dietary patterns, including prolonged fasting and high-fat low-carbohydrate dieting, can produce ketosis, in which acetone is formed in body tissue. Certain health conditions, such as alcoholism and diabetes, can produce ketoacidosis, uncontrollable ketosis that leads to a sharp, and potentially fatal, increase in the acidity of the blood. Since it is a byproduct of fermentation, acetone is a byproduct of the distillery industry.

Metabolic use

Although some biochemistry textbooks and current research publications[28] indicate that acetone cannot be metabolized, there is evidence to the contrary, some dating back thirty years.

Acetone can be produced from the oxidation of ingested isopropanol, or from the spontaneous/enzymatic breakdown of acetoacetate (a ketone body) in ketotic individuals. It can then be metabolized either by CYP2E1 via methylglyoxal to D-lactate and pyruvate, and ultimately glucose/energy, or by a different pathway via propylene glycol to pyruvate, lactate, acetate (usable for energy) and propionaldehyde.[29][30][31]

Production

In 2010, the worldwide production capacity for acetone was estimated at 6.7 million tonnes per year.[32] With 1.56 million tonnes per year, the United States had the highest production capacity,[33] followed by Taiwan and mainland China. The largest producer of acetone is INEOS Phenol, owning 17% of the world's capacity, with also significant capacity (7–8%) by Mitsui, Sunoco and Shell in 2010.[32] INEOS Phenol also owns the world's largest production site (420,000 tonnes/annum) in Beveren (Belgium). Spot price of acetone in summer 2011 was 1100–1250 USD/tonne in the United States.[34]

Current method

Acetone is produced directly or indirectly from propylene. Approximately 83% of acetone is produced via the cumene process;[17] as a result, acetone production is tied to phenol production. In the cumene process, benzene is alkylated with propylene to produce cumene, which is oxidized by air to produce phenol and acetone:

Overview of the cumene process
Overview of the cumene process

Other processes involve the direct oxidation of propylene (Wacker-Hoechst process), or the hydration of propylene to give 2-propanol, which is oxidized to acetone.[17]

Older methods

Previously, acetone was produced by the dry distillation of acetates, for example calcium acetate in ketonic decarboxylation.

Ca(CH3COO)2 → CaO(s) + CO2(g) + (CH3)2CO (v)

After that time, during World War I, acetone was produced using acetone-butanol-ethanol fermentation with Clostridium acetobutylicum bacteria, which was developed by Chaim Weizmann (later the first president of Israel) in order to help the British war effort,[17] in the preparation of Cordite.[35] This acetone-butanol-ethanol fermentation was eventually abandoned when newer methods with better yields were found.[17]

Uses

About a third of the world's acetone is used as a solvent, and a quarter is consumed as acetone cyanohydrin, a precursor to methyl methacrylate.[16]

Solvent

Acetone is a good solvent for many plastics and some synthetic fibers. It is used for thinning polyester resin, cleaning tools used with it, and dissolving two-part epoxies and superglue before they harden. It is used as one of the volatile components of some paints and varnishes. As a heavy-duty degreaser, it is useful in the preparation of metal prior to painting. It is also useful for high reliability soldering applications to remove rosin flux after soldering is complete; this helps to prevent the rusty bolt effect.

Acetone is used as a solvent by the pharmaceutical industry and as a denaturant in denatured alcohol.[36] Acetone is also present as an excipient in some pharmaceutical drugs.[37]

Although itself flammable, acetone is used extensively as a solvent for the safe transportation and storage of acetylene, which cannot be safely pressurized as a pure compound. Vessels containing a porous material are first filled with acetone followed by acetylene, which dissolves into the acetone. One liter of acetone can dissolve around 250 liters of acetylene at a pressure of 10 bar.[38][39]

Chemical intermediate

Acetone is used to synthesize methyl methacrylate. It begins with the initial conversion of acetone to acetone cyanohydrin:

(CH3)2CO + HCN → (CH3)2C(OH)CN

In a subsequent step, the nitrile is hydrolyzed to the unsaturated amide, which is esterified:

(CH3)2C(OH)CN + CH3OH → CH2=(CH3)CCO2CH3 + NH3

The third major use of acetone (about 20%)[16] is synthesizing bisphenol A. Bisphenol A is a component of many polymers such as polycarbonates, polyurethanes, and epoxy resins. The synthesis involves the condensation of acetone with phenol:

(CH3)2CO + 2 C6H5OH → (CH3)2C(C6H4OH)2 + H2O

Many millions of kilograms of acetone are consumed in the production of the solvents methyl isobutyl alcohol and methyl isobutyl ketone. These products arise via an initial aldol condensation to give diacetone alcohol.[17]

2 (CH3)2CO → (CH3)2C(OH)CH2C(O)CH3

Condensation with acetylene gives 2-methylbut-3-yn-2-ol, precursor to synthetic terpenes and terpenoids.

Laboratory

In the laboratory, acetone is used as a polar, aprotic solvent in a variety of organic reactions, such as SN2 reactions. The use of acetone solvent is critical for the Jones oxidation. It does not form an azeotrope with water (see azeotrope (data)).[40] It is a common solvent for rinsing laboratory glassware because of its low cost and volatility. Despite its common use as a supposed drying agent, it is not effective except by bulk displacement and dilution. Acetone can be cooled with dry ice to −78 °C without freezing; acetone/dry ice baths are commonly used to conduct reactions at low temperatures. Acetone is fluorescent under ultraviolet light, and its vapor can be used as a fluorescent tracer in fluid flow experiments.[41]

Acetone is used to precipitate proteins.[42] Alternatives for protein precipitation is trichloroacetic acid and ethanol.

Medical and cosmetic uses

Acetone is used in a variety of general medical and cosmetic applications and is also listed as a component in food additives and food packaging and also in nail polish remover. Dermatologists use acetone with alcohol for acne treatments to peel dry skin.

Acetone is commonly used in chemical peeling. Common agents used today for chemical peels are salicylic acid, glycolic acid, 30% salicylic acid in ethanol, and trichloroacetic acid (TCA). Prior to chemexfoliation, the skin is cleaned and excess fat removed in a process called defatting. Acetone, Septisol, or a combination of these agents is commonly used in this process.

Domestic and other niche uses

Acetone is often the primary component in cleaning agents such as nail polish remover. Acetone is a component of superglue remover and easily removes residues from glass and porcelain. Make-up artists use acetone to remove skin adhesive from the netting of wigs and mustaches by immersing the item in an acetone bath, then removing the softened glue residue with a stiff brush.

Acetone is often used for vapor polishing of printing artifacts on 3D-printed models printed with ABS plastic. The technique, called acetone vapor bath smoothing, involves placing the printed part in a sealed chamber containing a small amount of acetone, and heating to around 80 degrees Celsius for 10 minutes. This creates a vapor of acetone in the container. The acetone condenses evenly all over the part, causing the surface to soften and liquefy. Surface tension then smooths the semi-liquid plastic. When the part is removed from the chamber, the acetone component evaporates leaving a glassy-smooth part free of striation, patterning, and visible layer edges, common features in untreated 3D printed parts.[43]

Low-grade acetone is also commonly used in academic laboratory settings as a glassware rinsing agent for removing residue and solids before a final wash.[44]

Safety

Flammability

The most hazardous property of acetone is its extreme flammability. At temperatures greater than acetone's flash point of −20 °C (−4 °F), air mixtures of between 2.5% and 12.8% acetone, by volume, may explode or cause a flash fire. Vapors can flow along surfaces to distant ignition sources and flash back. Static discharge may also ignite acetone vapors, though acetone has a very high ignition initiation energy point and therefore accidental ignition is rare. Even pouring or spraying acetone over red-glowing coal will not ignite it, due to the high concentration of vapour and the cooling effect of evaporation of the liquid.[45] It auto-ignites at 465 °C (869 °F). Auto-ignition temperature is also dependent upon the exposure time, thus at some tests it is quoted as 525 °C. Also, industrial acetone is likely to contain a small amount of water which also inhibits ignition.

Acetone peroxide

When oxidized, acetone forms acetone peroxide as a byproduct, which is a highly unstable, primary high explosive compound. It may be formed accidentally, e.g. when waste hydrogen peroxide is poured into waste solvent containing acetone. Due to its instability, it is rarely used, despite its simple chemical synthesis.

Health information

Acetone has been studied extensively and is generally recognized to have low acute and chronic toxicity if ingested and/or inhaled.[46] Acetone is not currently regarded as a carcinogen, a mutagenic chemical nor a concern for chronic neurotoxicity effects.[45]

Acetone can be found as an ingredient in a variety of consumer products ranging from cosmetics to processed and unprocessed foods. Acetone has been rated as a generally recognized as safe (GRAS) substance when present in beverages, baked foods, desserts, and preserves at concentrations ranging from 5 to 8 mg/L.[46]

Acetone has been shown to have anticonvulsant effects in animal models of epilepsy, in the absence of toxicity, when administered in millimolar concentrations.[47] It has been hypothesized that the high-fat low-carbohydrate ketogenic diet used clinically to control drug-resistant epilepsy in children works by elevating acetone in the brain.[47] Because of their higher energy requirements, children have higher acetone production than most adults – and the younger the child, the higher the expected production. This indicates that children are not uniquely susceptible to acetone exposure. External exposures are small compared to the exposures associated with the ketogenic diet.[48]

Toxicology

Acetone is believed to exhibit only slight toxicity in normal use, and there is no strong evidence of chronic health effects if basic precautions are followed.[49]

Acetone is an irritant causing mild skin irritation and moderate to severe eye irritation. At high vapor concentrations, it may depress the central nervous system like many other solvents.[50] In one documented case, ingestion of a substantial amount of acetone led to systemic toxicity, although the patient eventually fully recovered. Some sources estimate LD50 for human ingestion at 0.621 g/kg; Acute toxicity for mice by ingestation (LD50) is 3 g/kg and by inhalation LC50) is 44 g/m3 over 4 hours.[51]

  • EPA EPCRA Delisting (1995). EPA removed acetone from the list of "toxic chemicals" maintained under Section 313 of the Emergency Planning and Community Right to Know Act (EPCRA). In making that decision, EPA conducted an extensive review of the available toxicity data on acetone and found that acetone "exhibits acute toxicity only at levels that greatly exceed releases and resultant exposures", and further that acetone "exhibits low toxicity in chronic studies".
  • Genotoxicity. Acetone has been tested in more than two dozen in vitro and in vivo assays. These studies indicate that acetone is not genotoxic.
  • Carcinogenicity. EPA in 1995 concluded, "There is currently no evidence to suggest a concern for carcinogenicity". (EPCRA Review, described in Section 3.3). NTP scientists have recommended against chronic toxicity/carcinogenicity testing of acetone because "the prechronic studies only demonstrated a very mild toxic response at very high doses in rodents".
  • Neurotoxicity and Developmental Neurotoxicity. The neurotoxic potential of both acetone and isopropanol, the metabolic precursor of acetone, have been extensively studied. These studies demonstrate that although exposure to high doses of acetone may cause transient central nervous system effects, acetone is not a neurotoxicant. A guideline developmental neurotoxicity study has been conducted with isopropanol, and no developmental neurotoxic effects were identified, even at the highest dose tested. (SIAR, pp. 1, 25, 31).
  • Environmental. When the EPA exempted acetone from regulation as a volatile organic compound (VOC) in 1995, EPA stated that this exemption would "contribute to the achievement of several important environmental goals and would support EPA's pollution prevention efforts". 60 Fed. Reg. 31,634 (June 16, 1995). 60 Fed. Reg. 31,634 (June 16, 1995). EPA noted that acetone could be used as a substitute for several compounds that are listed as hazardous air pollutants (HAP) under section 112 of the Clean Air Act.

Environmental effects

Although acetone occurs naturally in the environment in plants, trees, volcanic gases, forest fires, and as a product of the breakdown of body fat,[52] the majority of the acetone released into the environment is of industrial origin. Acetone evaporates rapidly, even from water and soil. Once in the atmosphere, it has a 22-day half-life and is degraded by UV light via photolysis (primarily into methane and ethane.[53]) Consumption by microorganisms contributes to the dissipation of acetone in soil, animals, or waterways.[52] The LD50 of acetone for fish is 8.3 g/L of water (or about 1%) over 96 hours, and its environmental half-life in water is about 1 to 10 days. Acetone may pose a significant risk of oxygen depletion in aquatic systems due to the microbial consumption.[54]

Extraterrestrial occurrence

On 30 July 2015, scientists reported that upon the first touchdown of the Philae lander on comet 67P's surface, measurements by the COSAC and Ptolemy instruments revealed sixteen organic compounds, four of which were seen for the first time on a comet, including acetamide, acetone, methyl isocyanate, and propionaldehyde.[55][56][57]

References

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External links

Acetoacetate decarboxylase

Acetoacetate decarboxylase (AAD or ADC) is an enzyme involved in both the ketone body production pathway in humans and other mammals, and solventogenesis in bacteria. Acetoacetate decarboxylase plays a key role in solvent production by catalyzing the decarboxylation of acetoacetate, yielding acetone and carbon dioxide. This enzyme has been of particular interest because it is a classic example of how pKa values of ionizable groups in the enzyme active site can be significantly perturbed. Specifically, the pKa value of lysine 115 in the active site is unusually low, allowing for the formation of a Schiff base intermediate and catalysis.

Acetone peroxide

Acetone peroxide is an organic peroxide and a primary high explosive. It is produced by the reaction of acetone and hydrogen peroxide to yield a mixture of linear monomer and cyclic dimer, trimer, and tetramer forms. The trimer is known as triacetone triperoxide (TATP) or tri-cyclic acetone peroxide (TCAP). The dimer is known as diacetone diperoxide (DADP). Acetone peroxide takes the form of a white crystalline powder with a distinctive bleach-like odor (when impure) or a fruit-like smell when pure and can explode if subjected to heat, friction, static electricity, concentrated sulfuric acid, strong UV radiation or shock. As a non-nitrogenous explosive, TATP has historically been more difficult to detect, and it has been used as an explosive in several terrorist attacks since 2001.

Acetone–butanol–ethanol fermentation

Acetone–butanol–ethanol (ABE) fermentation is a process that uses bacterial fermentation to produce acetone, n-Butanol, and ethanol from carbohydrates such as starch and glucose. It was developed by the chemist Chaim Weizmann and was the primary process used to make acetone during World War I, such as to produce cordite, a substance essential for the British war industry.

Acetylacetone

Acetylacetone is an organic compound with the formula CH3COCH2COCH3. It is a colorless liquid, classified as a 1,3-diketone. It exists in equilibrium with a tautomer CH3C(O)CH=C(OH)CH3. These tautomers interconvert so rapidly under most conditions that they are treated as a single compound in most applications. It is a colorless liquid that is a precursor to acetylacetonate anion (commonly abbreviated acac−), a bidentate ligand. It is also a building block for the synthesis of heterocyclic compounds.

Algestone acetonide

Algestone acetonide (developmental code name W-3395), also known as algestone 16α,17α-acetonide or 16α,17α-isopropylidenedioxyprogesterone, is a progestin which was never marketed. It is the acetonide cyclic ketal of algestone. Another progestin, algestone acetophenide, in contrast, has been marketed.

Arthur and the Acetone

Arthur and the Acetone (1936) is a satirical playlet by George Bernard Shaw which dramatises an imaginary conversation between the Zionist Chaim Weizmann and the British Foreign Secretary Arthur Balfour, which Shaw presents as the "true" story of how the Balfour Declaration came into being.

Bisphenol

The bisphenols () are a group of chemical compounds with two hydroxyphenyl functionalities. Most of them are based on diphenylmethane. The exceptions are bisphenol S, P, and M. "Bisphenol" is a common name; the letter following refers to one of the reactants. Bisphenol A is the most popular representative of this group, often simply called "bisphenol."

Butanone

Butanone, also known as methyl ethyl ketone (MEK), is an organic compound with the formula CH3C(O)CH2CH3. This colorless liquid ketone has a sharp, sweet odor reminiscent of butterscotch and acetone. It is produced industrially on a large scale, and also occurs in trace amounts in nature. It is soluble in water and is commonly used as an industrial solvent.

Cumene process

The cumene process (cumene-phenol process, Hock process) is an industrial process for synthesizing phenol and acetone from benzene and propylene. The term stems from cumene (isopropyl benzene), the intermediate material during the process. It was invented by Heinrich Hock in 1944 and independently by R. Ūdris and P. Sergeyev in 1942 (USSR).This process converts two relatively cheap starting materials, benzene and propylene, into two more valuable ones, phenol and acetone. Other reactants required are oxygen from air and small amounts of a radical initiator. Most of the worldwide production of phenol and acetone is now based on this method. In 2003, nearly 7 million tonnes of phenol was produced by the cumene process. In order for this process to be economical, there must also be demand for the acetone by-product as well as the phenol.

Dihydroxyacetone

Dihydroxyacetone (listen) (DHA), also known as glycerone, is a simple saccharide (a triose) with formula C3H6O3.

DHA is primarily used as an ingredient in sunless tanning products. It is often derived from plant sources such as sugar beets and sugar cane, and by the fermentation of glycerin.

Galanolactone

Galanolactone is a diterpenoid lactone first isolated from ginger. It is known to be present in acetone extracts of ginger, and appears to be an antagonist at 5-HT3 receptors.

Isopropyl alcohol

Isopropyl alcohol (IUPAC name propan-2-ol; commonly called isopropanol or 2-propanol) is a compound with the chemical formula CH3CHOHCH3. It is a colorless, flammable chemical compound with a strong odor. As an isopropyl group linked to a hydroxyl group, it is the simplest example of a secondary alcohol, where the alcohol carbon atom is attached to two other carbon atoms. It is a structural isomer of 1-propanol and ethyl methyl ether.

It is used in the manufacture of a wide variety of industrial and household chemicals, and is a common ingredient in chemicals such as antiseptics, disinfectants and detergents.

Ketoacidosis

Ketoacidosis is a metabolic state associated with high concentrations of ketone bodies, formed by the breakdown of fatty acids and the deamination of amino acids. The two common ketones produced in humans are acetoacetic acid and β-hydroxybutyrate.

Ketone

In chemistry, a ketone is an organic compound with the structure R(C=O)R', where R and R' can be a variety of carbon-containing substituents. Ketones and aldehydes are simple compounds that contain a carbonyl group (a carbon-oxygen double bond). They are considered "simple" because they do not have reactive groups like −OH or −Cl attached directly to the carbon atom in the carbonyl group, as in carboxylic acids containing −COOH. Many ketones are known and many are of great importance in industry and in biology. Examples include many sugars (ketoses) and the industrial solvent acetone, which is the smallest ketone.

Ketone bodies

Ketone bodies are three water-soluble molecules (acetoacetate, beta-hydroxybutyrate, and their spontaneous breakdown product, acetone) containing the ketone group that are produced by the liver from fatty acids during periods of low food intake (fasting), carbohydrate restrictive diets, starvation, prolonged intense exercise, alcoholism or in untreated (or inadequately treated) type 1 diabetes mellitus. These ketone bodies are readily picked up by the extra-hepatic tissues (tissues outside the liver) and converted into acetyl-CoA which then enters the citric acid cycle and is oxidized in the mitochondria for energy. In the brain, ketone bodies are also used to make acetyl-CoA into long-chain fatty acids.

Ketone bodies are produced by the liver under the circumstances listed above (i.e. fasting, starving, low carbohydrate diets, prolonged exercise and untreated type 1 diabetes mellitus) as a result of intense gluconeogenesis, which is the production of glucose from non-carbohydrate sources (not including fatty acids). They are therefore always released into the blood by the liver together with newly produced glucose after the liver glycogen stores have been depleted (these glycogen stores are depleted within the first 24 hours of fasting).When two acetyl-CoA molecules lose their -CoAs, (or Co-enzyme A groups) they can form a (covalent) dimer called acetoacetate. Beta-hydroxybutyrate is a reduced form of acetoacetate, in which the ketone group is converted into an alcohol (or hydroxyl) group (see illustration on the right). Both are 4-carbon molecules, that can readily be converted back into acetyl-CoA by most tissues of the body, with the notable exception of the liver. Acetone is the decarboxylated form of acetoacetate which cannot be converted back into acetyl-CoA except via detoxification in the liver where it is converted into lactic acid, which can, in turn, be oxidized into pyruvic acid, and only then into acetyl-CoA.

Ketone bodies have a characteristic smell, which can easily be detected in the breath of persons in ketosis and ketoacidosis. It is often described as fruity or like nail polish remover (which usually contains acetone or ethyl acetate).

Apart from the three endogenous ketone bodies, acetone, acetoacetic acid, and beta-hydroxybutyric acid, other ketone bodies like beta-ketopentanoate and beta-hydroxypentanoate may be created as a result of the metabolism of synthetic triglycerides, such as triheptanoin.

Oximinotransferase

In enzymology, an oximinotransferase (EC 2.6.3.1) is an enzyme that catalyzes the chemical reaction

pyruvate oxime + acetone pyruvate + acetone oxime

Thus, the two substrates of this enzyme are pyruvate oxime and acetone, whereas its two products are pyruvate and acetone oxime.

This enzyme belongs to the family of transferases, specifically those transferring nitrogenous groups oximinotransferases. The systematic name of this enzyme class is pyruvate-oxime:acetone oximinotransferase. Other names in common use include transoximinase, oximase, pyruvate-acetone oximinotransferase, and transoximase.

Propionaldehyde

Propionaldehyde or propanal is the organic compound with the formula CH3CH2CHO. It is a saturated 3-carbon aldehyde and is a structural isomer of acetone. It is a colorless liquid with a slightly irritating, fruity odor.

Solvent

A solvent (from the Latin solvō, "loosen, untie, solve") is a substance that dissolves a solute (a chemically distinct liquid, solid or gas), resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. The quantity of solute that can dissolve in a specific volume of solvent varies with temperature. Common uses for organic solvents are in dry cleaning (e.g. tetrachloroethylene), as paint thinners (e.g. toluene, turpentine), as nail polish removers and glue solvents (acetone, methyl acetate, ethyl acetate), in spot removers (e.g. hexane, petrol ether), in detergents (citrus terpenes) and in perfumes (ethanol). Water is a solvent for polar molecules and the most common solvent used by living things; all the ions and proteins in a cell are dissolved in water within a cell. Solvents find various applications in chemical, pharmaceutical, oil, and gas industries, including in chemical syntheses and purification processes.

Sulfonmethane

Sulfonmethane (Sulfonomethane, Sulfonal, Acetone diethyl sulfone) is a chemical compound first synthesized by Eugen Baumann in 1888 and introduced as a hypnotic drug by Alfred Kast later on, but now superseded by newer and safer sedatives. Its appearance is either in colorless crystalline or powdered form. In United States, it is scheduled as a Schedule III drug in the Controlled Substance Act.

Mevalonate pathway
Non-mevalonate pathway
To Cholesterol
From Cholesterol
(to steroids)
Steroid hormones
Nonhuman
Alcohols
Barbiturates
Benzodiazepines
Carbamates
Flavonoids
Imidazoles
Kava constituents
Monoureides
Neuroactive steroids
Nonbenzodiazepines
Phenols
Piperidinediones
Pyrazolopyridines
Quinazolinones
Volatiles/gases
Others/unsorted
Molecules
Deuterated
molecules
Unconfirmed
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