55449-44-0

Basic information

• Product Name: methyl (2R)-2-methylbutanoate
• Synonyms: butanoic acid, 2-methyl-, methyl ester, (2R)-; Butanoic acid, 2-methyl-, methyl ester, (R)-; Methyl (R)-2-methylbutanoate
• CAS NO: 55449-44-0
• Molecular Formula: C₆H₁₂O₂
• Molecular Weight: 116.1583
• Mol File: 55449-44-0.mol

Chemical Properties

• Boiling Point: 112.6°C at 760 mmHg
• Flash Point: 19.4°C
• Density: 0.883g/cm³
• Vapor Pressure: 21.6mmHg at 25°C
• Refractive Index: 1.395
• CAS DataBase Reference: methyl (2R)-2-methylbutanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2R)-2-methylbutanoate(55449-44-0)
• EPA Substance Registry System: methyl (2R)-2-methylbutanoate(55449-44-0)

Safety Data

• Hazardous Substances Data: 55449-44-0(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 32231-50-8 (R)-2-methylbutyric acid 
• 67-56-1 methanol 
• 80-59-1 Tiglic acid 
• 250359-29-6 (R)-3-methyl-4-tetrahydropyranyloxybutyl tosylate 
• 250359-28-5 tert-butyl (R)-3-methyl-4-tetrahydropyranyloxybutanoate 
• 185836-76-4 tert-butyl (R)-4-hydroxy-3-methylbutanoate 
• 185836-75-3 (R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid 
• 170717-85-8 (R)-3-Methyl-4-<(tetrahydropyranyl)oxy>butan-1-ol 
• 130856-00-7 (R)-2-methyl-1-(2-tetrahydropyranyloxy)butane 
• 616-16-0 (R)-2-Methyl-1-butanol 
• 101400-29-7 (S)-2-Methylbutyroyl chloride 

Relevant articles and documents

Enantiomeric ratios of 2-methylbutanoic acid and its methyl ester: Elucidation of novel biogenetic pathways towards (R)-methyl 2-methylbutanoate in a beverage fermented with shiitake

Up to 35% of (R)-methyl 2-methylbutanoate (M2MB) was observed in a beverage fermented with shiitake. As M2MB naturally occurs typically in high excesses of the (S)-enantiomer, the origin of the (R)-ester was elucidated by stable isotope labeled precursor-feeding studies. (R)-2-Methylbutanoic acid was identified as the main precursor in the substrate wort. Trace amounts of (R)-M2MB were produced by transformation of unsaturated secondary metabolites (tiglic aldehyde and tiglic acid) derived from L-isoleucine. Surprisingly, shiitake esterified (R)-2-methylbutanoic acid faster to (R)-M2MB than the corresponding (S)-enantiomer. Concurrently, spontaneous non-enantioselective degradation of M2MB occurred in shiitake. This explains diverse enantiomeric ratios of M2MB and different enantiomeric ratios of 2-methylbutanoic acid and M2MB in the beverage. As the odor threshold values of (R)-and (S)-M2MB differ significantly, these findings are of high relevance for the overall flavor of the fermented beverage and elucidate the discrepancy of enantiomeric ratios of 2-alkyl-branched acids and esters reported in nature.

Heterogeneous catalytic hydrogenation of olefinic substrates by poly-NAP

With our previously described poly-NAP, various olefinic substrates were reduced with selectivities comparable to those obtained by BINAP. For substrates which contained a methyl ester, the selectivities were higher than those observed for their carboxylic acid analogues. (C) 2000 Elsevier Science Ltd.

Pheromone synthesis, CXCVII. Synthesis of the enantiomers of 2-sec- butyl-4,5-dihydrothiazole and (1R,5S,7R)-3,4-dehydro-exo-brevicomin, pheromone components of the male mouse, Mus musculus

Two components [2-sec-butyl-4,5-dihydrothiazole (1) and 3,4-dehydro-exo- brevicomin (2)] of a male-produced pheromone of the mouse Mus musculus have been synthesized in optically active forms. The enantiomers of 1 were obtained with an enantiomeric purity of ca. 92% ee and were found to be readily racemizable. Asymmetric dihydroxylation was employed as the key reaction (15→16) allowing the preparation of (1R,5S,7R)-2 with ca. 94% ee.