2-Methylbutanoic acid

Carboxylic acid (R)-2-Methyl Butyric Acid-Structural Formula V.1.svg skin-invert (S)-2-Methyl Butyric Acid-Structural Formula V.1.svg skin-invert 2-Methylbutanoic acid 2-Methylbutyric acidMethylethylacetic acid R/S R S 116-53-0 correct CAS 32231-50-8 correct CAS 1730-91-2 correct CAS correct FDA PX7ZNN5GXK correct FDA 5N31513I0N 8314 6950479 448893 correct chemspider 8012 5323416 395556 37070 45525 38655 204-145-2 1160012 1098537 C18319 DTXSID5021621 1S/C5H10O2/c1-3-4(2)5(6)7/h4H,3H2,1-2H3,(H,6,7) WLAMNBDJUVNPJU-UHFFFAOYSA-N WLAMNBDJUVNPJU-SCSAIBSYSA-N WLAMNBDJUVNPJU-BYPYZUCNSA-N CCC(C)C(=O)O 492807 C5H10O2 Clear colorless liquid 0.94 g/cm3 (20 °C) -90 176 1.18 83 05 07 Danger 302 312 314 260 264 270 280 301+312 301+330+331 302+352 303+361+353 304+340 305+351+338 310 312 321 322 330 363 405 501 2-Methylbutanoic acid, also known as 2-methylbutyric acid, is a branched-chain alkyl carboxylic acid with the chemical formula CH3CH2CH(CH3)CO2H. It is classified as a short-chain fatty acid. It exists in two enantiomeric forms, (R)- and (S)-2-methylbutanoic acid. (R)-2-methylbutanoic acid occurs naturally in cocoa beans and (S)-2-methylbutanoic occurs in many fruits such as apples and apricots,10.1016/S0957-4166(00)86137-6 Chiral 2-alkylbranched acids, esters and alcohols. Preparation and stereospecific flavour evaluation 1991 Rettinger Klaus Burschka Christian Scheeben Peter Fuchs Heike Mosandl Armin Tetrahedron: Asymmetry 2 10 965–968 https://opus.bibliothek.uni-wuerzburg.de/files/4494/Burschka_Esters.pdf Karl A. D. Swift Current Topics in Flavours and Fragrances: Towards a New Millennium of Discovery Springer 0-7514-0490-X 1999 52 as well as in the scent of the orchid Luisia curtisii.Genera Orchidacearum Vol 6, Ed. Alec M. Pridgeon et al., p. 207 (LUISIA). History 2-Methylbutanoic acid is a minor constituent of Angelica archangelica and the perennial flowering plant valerian (Valeriana officinalis), where it co-occurs with valeric acid and isovaleric acid.Valeric Acid 27 859 The dried root of this plant has been used medicinally since antiquity.10.1111/j.0013-9580.2004.27904.x 15509234 45 11 1338–1343 Eadie Mervyn J. Could Valerian Have Been the First Anticonvulsant? Epilepsia November 2004 free The chemical identity of all three compounds was first investigated in the 19th century by oxidation of the components of fusel alcohol, which includes the five-carbon amyl alcohols. Among the products isolated was a compound which gave a (+) rotation in polarised light, indicating it to be the (2S) isomer.10.1039/JS8682100074 On the isomeric forms of valeric acid 1868 Pedler Alexander Journal of the Chemical Society 21 74–76 https://zenodo.org/record/2175638 free Preparation Racemic 2-methylbutanoic acid can readily be prepared by a Grignard reaction using 2-chlorobutane, magnesium and carbon dioxide.10.15227/orgsyn.005.0075 free dl-Methylethylacetic acid Organic Syntheses 1925 5 75 It was the target of the first enantioselective synthesis in 1904 when the German chemist W. Marckwald heated ethyl(methyl)malonic acid with the chiral base brucine and obtained an optically active product mixture. 10.1002/cber.19040370165 Ueber asymmetrische Synthese Berichte der Deutschen Chemischen Gesellschaft 37 349–354 1904 Marckwald W https://zenodo.org/record/1426100 Either enantiomer of 2-methylbutanoic acid can now be obtained by asymmetric hydrogenation of tiglic acid using a ruthenium-BINAP catalyst.10.1016/S1381-1169(98)00235-0 Asymmetric hydrogenation by an in situ prepared (S)-BINAP–Ru(II) catalytic system 1999 Matteoli Ugo Beghetto Valentina Scrivanti Alberto Journal of Molecular Catalysis A: Chemical 140 2 131–137 Reactions The compound and its enantiomers react as typical carboxylic acids: they can form amide, ester, anhydride, and chloride derivatives.10.1039/9781847556196-00096 Carboxylic acids and derivatives General and Synthetic Methods 1985 Jenkins P. R. 7 96–160 978-0-85186-884-4 The acid chloride is commonly used as the intermediate to obtain the others. Uses Racemic 2-methylbutanoic acid is a slightly volatile, colorless liquid with a pungent cheesy odor.http://www.thegoodscentscompany.com/data/rw1056421.html 2-Methylbutyric acid The Good Scents Company 2020-09-30 The smell differs significantly between the two enantiomeric forms. (S)-2-Methylbutyric acid has a pleasantly sweet, fruity odorhttp://www.thegoodscentscompany.com/data/rw1141241.html (S)-2-methylbutyric acid The Good Scents Company 2020-09-30 while (R)-2-methylbutanoic acid has a pervasive, cheesy, sweaty odor.http://www.thegoodscentscompany.com/data/rw1620751.html (R)-2-methylbutyric acid The Good Scents Company 2020-09-30 The main use of the materials, and their esters, is therefore as flavours and food additives.10.1007/s002170000250 Occurrence of volatile chiral compounds in dairy products, especially cheese - A review 2001 Mariaca Raul G. Imhof Miroslava I. Bosset J. O. European Food Research and Technology 212 3 253–261 96864200 The compounds' safety in this application was reviewed by an FAO and WHO panel, who concluded that there were no concerns at the likely levels of intake.http://www.inchem.org/documents/jecfa/jecmono/v040je11.htm Safety evaluation of certain food additives and contaminants FAO/WHO Expert Committee on food additives 1998 2020-09-30 Biology Since 2-methylbutanoic acid and its esters are natural components of many foods, they are present in mammals including humans.https://hmdb.ca/metabolites/HMDB0033742 Metabocard for (S)-2-Methylbutanoic acid Human Metabolome Database 2020-09-30 2019-07-23 https://hmdb.ca/metabolites/HMDB0029762 Metabocard for Methyl (S)-2-Methylbutanoate Human Metabolome Database 2020-09-30 2019-07-23 See also 3-Methylbutanoic acid, an isomer Valeric acid, an isomer References External links 2-Methylbutanoic acid Category:Flavors Category:Alkanoic acids