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( R e d i r e c t e d f r o m I s o v a l e r i c a c i d )
Carboxylic acid with chemical formula (CH3)2CHCH2CO2H CH3CH2
3-Methylbutanoic acid
Names
Preferred IUPAC name
Other names
Delphinic acid
Identifiers
CAS Number
3D model (JSmol )
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.251
EC Number
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA )
InChI=1S/C5H10O2/c1-4(2 )3-5(6 )7/h4H,3H2,1-2H3,(H,6,7) Y
Key: GWYFCOCPABKNJV-UHFFFAOYSA-N Y
InChI=1/C5H10O2/c1-4(2 )3-5(6 )7/h4H,3H2,1-2H3,(H,6,7)
Key: GWYFCOCPABKNJV-UHFFFAOYAV
Properties
Chemical formula
C 5 H 10 O 2
Molar mass
102.13 g/mol
Density
0.925 g/cm3
Melting point
−29 °C (−20 °F; 244 K )
Boiling point
176.5 °C (349.7 °F; 449.6 K )
log P
1.16
Acidity (p K a 4.8 (H 2 O )
Magnetic susceptibility (χ)
-67.7·10−6 cm 3
Related compounds
Related carboxylic acids
butyric acid β-hydroxybutyric acid β-hydroxy β-methylbutyric acid
Related compounds
Valeric acid
Hazards
GHS labelling[1]
Pictograms
Signal word
Danger
Hazard statements
H314
Precautionary statements
P280 , P301+P330+P331 , P303+P361+P353 , P304+P340+P310 , P305+P351+P338 , P363
Flash point
80 °C (176 °F; 353 K )
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
3-Methylbutanoic acid , also known as β-methylbutyric acid or more commonly isovaleric acid , is a branched-chain alkyl carboxylic acid with the chemical formula (CH 3 2 2 CO 2 short-chain fatty acid . Like other low-molecular-weight carboxylic acids, it has an unpleasant odor . The compound occurs naturally and can be found in many foods, such as cheese, soy milk, and apple juice.
History [ edit ]
3-Methylbutanoic acid is a minor constituent of the perennial flowering plant valerian (Valeriana officinalis trivial name isovaleric acid: an isomer of valeric acid which shares its unpleasant odor.[2] [3] [4] fusel alcohol , which includes the five-carbon amyl alcohols .[5]
Manufacture [ edit ]
In industry, 3-methylbutanoic acid is produced by the hydroformylation [6] of isobutylene with syngas , forming isovaleraldehyde ,[7] oxidised to the final product.[8]
(CH 3 2 2 2 CH 3 2 2
Reactions [ edit ]
3-Methylbutanoic acid reacts as a typical carboxylic acid: it can form amide , ester , anhydride , and chloride derivatives.[9] β-hydroxy β-methylbutyric acid – via microbial oxidation by the fungus Galactomyces reessii [10]
Alternative syntheses of β-hydroxy β-methylbutyric acid
Isovaleric acid has a strong pungent cheesy or sweaty smell,[11] esters such as ethyl isovalerate [12] Brettanomyces [13] Brettanomyces yeasts include 4-ethylphenol , 4-vinylphenol , and 4-ethylguaiacol .[14] [14] [13] Brettanomyces yeasts, such as by sterile filtration , by the addition of relatively large quantities of sulfur dioxide and sometimes sorbic acid , by mixing in alcoholic spirit to give a fortified wine of sufficient strength to kill all yeast and bacteria, or by pasteurization . Isovaleric acid can also be found in beer, and, excepting some English–style ales, is usually considered a flaw.[15] hop resins, or by Brettanomyces yeasts present.[15]
The compound's safety as a food additive was reviewed by an FAO and WHO panel, who concluded that there were no concerns at the likely levels of intake.[16]
Biology [ edit ]
Since isovaleric acid and its esters are natural components of many foods, it is present in mammals including humans.[17] Isovaleryl-coenzyme A is an intermediate in the metabolism of branched-chain amino acids .[18]
Isovaleric acid is a major component of the cause of intense foot odor , as it is produced by skin bacteria metabolizing leucine and in rare cases a condition called isovaleric acidemia can lead to heightened levels of this metabolite.[19]
Salts and esters [ edit ]
An isovalerate or 3-methylbutanoate ion is (CH 3 2 2 − , the conjugate base of the acid. It is the form found in biological systems at physiological pH . An isovalerate or 3-methylbutanoate compound is a salt or ester of the acid.
Examples [ edit ]
See also [ edit ]
References [ edit ]
^ Patočka, Jiří; Jakl, Jiří (2010). "Biomedically relevant chemical constituents of Valeriana officinalis " . Journal of Applied Biomedicine . 8 doi :10.2478/v10136-009-0002-z
^ Eadie, Mervyn J. (November 2004). "Could Valerian Have Been the First Anticonvulsant?" . Epilepsia . 45 11 ): 1338–1343. doi :10.1111/j.0013-9580.2004.27904.x PMID 15509234 . S2CID 7314227 .
^ Pedler, Alexander (1868). "On the isomeric forms of valeric acid" . Journal of the Chemical Society . 21 doi :10.1039/JS8682100074 .
^ Franke, Robert; Selent, Detlef; Börner, Armin (2012). "Applied Hydroformylation". Chemical Reviews . 112 (11 ): 5675–5732. doi :10.1021/cr3001803 . PMID 22937803 .
^ Kohlpaintner, Christian; Schulte, Markus; Falbe, Jürgen; Lappe, Peter; Weber, Jürgen; Frey, Guido D. (2013). "Aldehydes, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry . doi :10.1002/14356007.a01_321.pub3 . ISBN 978-3527306732
^ Riemenschneider, Wilhelm (2000). "Carboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry . doi :10.1002/14356007.a05_235 . ISBN 3527306730
^ Jenkins, P. R. (1985). "Carboxylic acids and derivatives". General and Synthetic Methods . Vol. 7. pp. 96–160. doi :10.1039/9781847556196-00096 . ISBN 978-0-85186-884-4
^ Lee IY, Nissen SL, Rosazza JP (1997). "Conversion of beta-methylbutyric acid to beta-hydroxy-beta-methylbutyric acid by Galactomyces reessii" . Applied and Environmental Microbiology . 63 11 ): 4191–5. Bibcode :1997ApEnM..63.4191L . doi :10.1128/AEM.63.11.4191-4195.1997 . PMC 168736 PMID 9361403 .
^ "Isovaleric acid" . The Good Scents Company . Retrieved 2020-09-30 .
^ "Ethyl 3-methylbutanoate" . The Good Scents Company . Retrieved 2020-09-30 .
^ a b Jackson, Ron S. (2008). Wine Science: Principles and Applications ISBN 9780123736468
^ a b Kirk-Othmer (2007). "Wine" . Food and Feed Technology, Volume 2 . John Wiley & Sons. p. 702. ISBN 9780470174487
^ a b Oliver, Garrett, ed. (2012). The Oxford Companion to Beer ISBN 9780195367133
^ FAO/WHO Expert Committee on food additives (1998). "Safety evaluation of certain food additives and contaminants" . Retrieved 2020-09-30 .
^ "Metabocard for Isovaleric acid" . Human Metabolome Database . 2020-02-26. Retrieved 2020-09-30 .
^ Wilson, Jacob M.; Fitschen, Peter J.; Campbell, Bill; Wilson, Gabriel J.; Zanchi, Nelo; Taylor, Lem; Wilborn, Colin; Kalman, Douglas S.; Stout, Jeffrey R.; Hoffman, Jay R.; Ziegenfuss, Tim N.; Lopez, Hector L.; Kreider, Richard B.; Smith-Ryan, Abbie E.; Antonio, Jose (2013). "International Society of Sports Nutrition Position Stand: Beta-hydroxy-beta-methylbutyrate (HMB)" . Journal of the International Society of Sports Nutrition . 10 1 ): 6. doi :10.1186/1550-2783-10-6 PMC 3568064 PMID 23374455 .
^ Ara, Katsutoshi; Hama, Masakatsu; Akiba, Syunichi; Koike, Kenzo; Okisaka, Koichi; Hagura, Toyoki; Kamiya, Tetsuro; Tomita, Fusao (April 2006). "Foot odor due to microbial metabolism and its control". Canadian Journal of Microbiology . 52 4 ): 357–364. CiteSeerX 10.1.1.1013.4047 doi :10.1139/w05-130 . PMID 16699586 .
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See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=3-Methylbutanoic_acid&oldid=1186937850 " C a t e g o r i e s : ● F l a v o r s ● A l k a n o i c a c i d s ● H e m i t e r p e n e s ● A c i d s i n w i n e ● G A B A a n a l o g u e s ● G A B A A r e c e p t o r p o s i t i v e a l l o s t e r i c m o d u l a t o r s H i d d e n c a t e g o r i e s : ● W i k i p e d i a a r t i c l e s i n c o r p o r a t i n g a c i t a t i o n f r o m t h e 1 9 1 1 E n c y c l o p a e d i a B r i t a n n i c a w i t h W i k i s o u r c e r e f e r e n c e ● A r t i c l e s w i t h s h o r t d e s c r i p t i o n ● S h o r t d e s c r i p t i o n i s d i f f e r e n t f r o m W i k i d a t a ● E C H A I n f o C a r d I D f r o m W i k i d a t a ● C h e m b o x h a v i n g G H S d a t a ● A r t i c l e s c o n t a i n i n g u n v e r i f i e d c h e m i c a l i n f o b o x e s ● C h e m b o x i m a g e s i z e s e t ● S h o r t d e s c r i p t i o n m a t c h e s W i k i d a t a
● T h i s p a g e w a s l a s t e d i t e d o n 2 6 N o v e m b e r 2 0 2 3 , a t 1 2 : 2 9 ( U T C ) . ● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n . ● P r i v a c y p o l i c y ● A b o u t W i k i p e d i a ● D i s c l a i m e r s ● C o n t a c t W i k i p e d i a ● C o d e o f C o n d u c t ● D e v e l o p e r s ● S t a t i s t i c s ● C o o k i e s t a t e m e n t ● M o b i l e v i e w
