Isobutyric acid
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Names | |||
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Preferred IUPAC name
2-Methylpropanoic acid[2] | |||
Other names
Isobutyric acid
2-Methylpropionic acid Isobutanoic acid | |||
Identifiers | |||
3D model (
JSmol ) |
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3DMet | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
DrugBank | |||
ECHA InfoCard
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100.001.087 | ||
EC Number |
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IUPHAR/BPS |
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KEGG | |||
PubChem CID
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RTECS number
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UNII | |||
UN number | 2529 | ||
CompTox Dashboard (EPA)
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Properties | |||
C4H8O2 | |||
Molar mass | 88.11 g/mol | ||
Density | 0.9697 g/cm3 (0 °C) | ||
Melting point | −47 °C (−53 °F; 226 K) | ||
Boiling point | 155 °C (311 °F; 428 K) | ||
Acidity (pKa) | 4.86[3] | ||
-56.06x10−6 cm3/mol | |||
Hazards[4][5] | |||
GHS labelling: | |||
Danger | |||
H226, H302, H311, H314 | |||
P210, P280, P301+P312+P330, P303+P361+P353, P305+P351+P338+P310 | |||
NFPA 704 (fire diamond) | |||
Flash point | 55 °C (131 °F; 328 K) | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Isobutyric acid, also known as 2-methylpropanoic acid or isobutanoic acid, is a
. Deprotonation or esterification gives derivatives called isobutyrates.Isobutyric acid is a colorless liquid with a somewhat unpleasant odor. It is soluble in water and organic solvents. It is found naturally in
Production
Isobutyric acid is manufactured by the oxidation of isobutyraldehyde, which is a byproduct of the hydroformylation of propylene.[7]
It can also be prepared by the high pressure
- CH3CH=CH2 + CO + H2O → (CH3)2CHCO2H
Isobutyric acid can also be manufactured commercially using engineered bacteria with a sugar feedstock.[8]
Laboratory methods
Many routes are known including the
Reactions
The acid reacts as a typical carboxylic acid: it can form amide, ester, anhydride, and chloride derivatives.[10] Its acid chloride is commonly used as the intermediate to obtain the others. When heated with a chromic acid solution it is oxidized to acetone. Alkaline potassium permanganate oxidizes it to α-hydroxyisobutyric acid, (CH3)2C(OH)-CO2H.[6]
Uses
Isobutyric acid and its volatile
Biology
In humans, isobutyric acid is a minor product of the
The metabolism of isobutyric acid in plants has been studied.[16]
Isobutyric acid, along with several other short-chain fatty acids collectively known as "copulins," is found abundantly in human vaginal secretions. Levels of isobutyric acid fluctuate throughout the menstrual cycle, and it is hypothesized to act as an indicator of ovulatory status.[17] Similar cycles are observed in chimpanzees.[18]
See also
References
- ^ Merck Index, 11th Edition, 5039
- ISBN 978-0-85404-182-4.
- ^ Bjerrum, J.; et al. (1958). Stability Constants. London: Chemical Society.
- ^ Sigma-Aldrich. "Isobutyric acid". Retrieved 2020-10-03.
- ^ "NFPA Hazard Classification". Retrieved 2020-10-03.
- ^ a b c Chisholm, Hugh, ed. (1911). . Encyclopædia Britannica. Vol. 4 (11th ed.). Cambridge University Press. p. 892.
- ^ )
- ^ "Biological pathways to produce methacrylate". Archived from the original on 2012-05-02. Retrieved 2011-10-07.
- ^ I. Pierre and E. Puchot (1873). "New Studies on Valerianic Acid and its Preparation on a Large Scale". Ann. Chim. Phys. 28: 366.
- ISBN 978-0-85186-884-4.
- ^ "Isobutyric acid". The Good Scents Company. Retrieved 2020-10-03.
- ^ FAO/WHO Expert Committee on food additives (1998). "Safety evaluation of certain food additives and contaminants". Retrieved 2020-09-30.
- ^ "Metabocard for isobutyric acid". Human Metabolome Database. 2020-03-26. Retrieved 2020-09-30.
- . Retrieved 2020-10-03.
- S2CID 4222453.
- S2CID 7143228.
- PMC 10426864.
- PMID 12778908.