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(R)-2-methyl butyric acid

(R)-2-methyl butyric acid is a chiral carboxylic acid characterized by a cheesy odor and is not utilized in fragrance or flavor applications.
Chemical Structure

General Material Description

(R)-2-methyl butyric acid is an organic compound belonging to the class of short-chain carboxylic acids known as fatty acids. Structurally, it is a chiral molecule with the molecular formula C5H10O2. It appears as a clear, colorless liquid possessing a characteristic cheesy and sweaty odor. This compound is also known under various synonyms including (-)-2-Methylbutanoic acid and (2R)-2-methylbutanoic acid. The compound is listed in chemical databases such as ChEBI. Sourced typically through synthetic organic chemistry processes, it does not occur abundantly in nature. Its primary interest lies in research and chemical manufacturing contexts rather than commercial fragrance or flavor applications.

Occurrence, Applicability & Potential Uses

(R)-2-methyl butyric acid has limited natural occurrence and is predominantly obtained via synthesis. It is a stereoisomer of 2-methylbutyric acid, a compound that can be present in certain biological processes related to fatty acid metabolism. Its practical applications are mainly informational and experimental; currently, it is not used for fragrance or flavor formulation. Chemical safety standards and regulations such as REACH (European Union) recognize the substance but classify it primarily for research or industrial use. Due to its odor profile and chemical properties, the compound is studied for analytical purposes but lacks approved commercial applications in consumer products.

Physico-Chemical Properties Summary

(R)-2-methyl butyric acid exhibits a molecular weight of approximately 102.13 g/mol. It is a chiral carboxylic acid with moderate water solubility, estimated around 28,110 mg/L at 25 °C. The compound displays a flash point measured at approximately 0 °C (32 °F), reflecting its volatility and flammability characteristics under ambient conditions. These properties influence its handling and storage requirements in laboratory environments. Its odor, described as cheesy and sweaty, results from its molecular structure and affects its sensory perception. The compound’s stereochemistry plays a role in its physicochemical behavior, including receptor interactions in sensory evaluation contexts.

FAQ

What is (R)-2-methyl butyric acid and what are its key characteristics?
(R)-2-methyl butyric acid is a chiral organic acid belonging to the class of short-chain carboxylic acids with the molecular formula C5H10O2. It is characterized by a cheesy and sweaty odor and exists as one stereoisomer among others of 2-methylbutyric acid. The compound is typically a clear, colorless liquid and is known under several synonyms including (-)-2-Methylbutanoic acid. It is primarily used in chemical research as opposed to commercial flavor or fragrance applications.
How and where is (R)-2-methyl butyric acid used or found?
(R)-2-methyl butyric acid occurs sparingly in nature and is mainly produced by synthesis for research or industrial purposes. It is present as a stereoisomeric form of 2-methylbutyric acid, which can sometimes be found as metabolic intermediates in biological systems. No established flavor or fragrance uses exist for this compound, and its primary applications are informational or experimental. Its use is governed by standard chemical safety protocols, emphasizing handling precautions due to its physical properties.
What regulations and safety considerations apply to (R)-2-methyl butyric acid?
(R)-2-methyl butyric acid is subject to chemical regulatory frameworks such as REACH in the European Union, where it is classified for research and industrial use. Safety data indicates no officially classified hazards under OSHA HCS (29 CFR 1910) guidelines, and no precautionary statements are mandated. Due to limited use in consumer products, recommended usage levels in flavors or fragrances are not established, and the compound is generally not employed in these sectors. Safety considerations focus on standard laboratory handling practices.

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

Leffingwell:Chirality or Article
(2R)-2-methylbutanoic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):6950479
Pubchem (sid):43558513
Publications by PubMed
Structural and Functional Analysis of the Loading Acyltransferase from Avermectin Modular Polyketide Synthase.
Biodegradation of C5-C 8 fatty acids and production of aroma volatiles by Myroides sp. ZB35 isolated from activated sludge.
Study on pharmacokinetics and tissue distribution of pteryxin in mice by ultra-pressure liquid chromatography with tandem mass spectrometry.
Pivalic acid acts as a starter unit in a fatty acid and antibiotic biosynthetic pathway in Alicyclobacillus, Rhodococcus and Streptomyces.
Stereoselective biocatalytic synthesis of (S)-2-hydroxy-2-methylbutyric acid via substrate engineering by using "thio-disguised" precursors and oxynitrilase catalysis.
Absolute configuration of the creatonotines and callimorphines, two classes of arctiid-specific pyrrolizidine alkaloids.
Requirements for the formation of a chiral template.
Chiral templating of surfaces: adsorption of (S)-2-methylbutanoic acid on Pt(111) single-crystal surfaces.
Asymmetric oxidation by Gluconobacter oxydans.
Enantiomers of cis-constrained and flexible 2-substituted GABA analogues exert opposite effects at recombinant GABA(C) receptors.
Stable isotope dilution analysis of wine fermentation products by HS-SPME-GC-MS.
2-ethylhydracrylic aciduria in short/branched-chain acyl-CoA dehydrogenase deficiency: application to diagnosis and implications for the R-pathway of isoleucine oxidation.
Role of alpha-methylacyl coenzyme A racemase in the degradation of methyl-branched alkanes by Mycobacterium sp. strain P101.
Total synthesis and biological evaluation of +-kalkitoxin, a cytotoxic metabolite of the cyanobacterium Lyngbya majuscula.
Enantioselective analysis of methyl-branched alcohols and acids in rhubarb (Rheum rhabarbarum L.) stalks.
Metabolism of ethyl tiglate in apple fruits leads to the formation of small amounts of (R)-ethyl 2-methylbutanoate.
Simultaneous enantioseparation of flobufen and its diastereomeric metabolites on ULMO, a Pirkle type chiral stationary phase.
Enantiomeric synthesis of (S)-2-methylbutanoic acid methyl ester, apple flavor, using lipases in organic solvent.
Components of the ether-insoluble resin glycoside-like fraction from Cuscuta chinensis.
Separation of the stereoisomers of the main metabolite of a non-steroidal anti-inflammatory drug, flobufen, by chiral high-performance liquid chromatography.
Branched-chain fatty acid requirement for avermectin production by a mutant of Streptomyces avermitilis lacking branched-chain 2-oxo acid dehydrogenase activity.
Stereoselectivity in the 2-methylbutyrate incorporation into anteiso fatty acids in Bacillus subtilis mutants.
Synthesis of stereoisomers of 8-methyl-2-decanol and esters attractive to severalDiabrotica sp.
Use of predator odors as repellents to reduce feeding damage by herbivores : I. Snowshoe hares (Lepus americanus).
Stereoselectivity of 1-aminocyclopropanecarboxylate malonyltransferase toward stereoisomers of 1-amino-2-ethylcyclopropanecarboxylic acid.
Studies of the glycine metabolism in a patient with D-glyceric acidemia and hyperglycinemia.
Demonstration of a new mammalian isoleucine catabolic pathway yielding an Rseries of metabolites.
Volatile fatty acid requirements of cellulolytic rumen bacteria.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
HMDB (The Human Metabolome Database):Search
ChemSpider:View

General Material Information

Preferred name (R)-2-methyl butyric acid
Trivial Name (-)-2-Methylbutanoic acid
Short Description butanoic acid, 2-methyl-, (R)-
Formula C5 H10 O2
CAS Number 32231-50-8
FDA UNII Search
Nikkaji Number J57.315I
Bio Activity Summary External link
NMR Predictor External link
Synonyms
  • butanoic acid, 2-methyl-, (R)-
  • (R)-2-methyl butanoic acid
  • (2R)-2-methylbutanoic acid
  • (R)-2-methylbutanoic acid
  • (R)-2-methylbutyric acid
  • Butanoic acid, 2-methyl-, (2R)-
  • Butyric acid, 2-methyl-, (-)-
  • (2R)-2-Methylbutanoic acid
  • (R)-2-Methylbutanoic acid
  • (R)-2-Methylbutyric acid
  • (-)-2-Methylbutyric acid
  • (R)-(-)-2-Methylbutanoic acid
  • (-)-2-Methylbutanoic acid
  • (-)-α-Methylbutyric acid
  • (R)-(-)-2-Methylbutyric acid

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 102.13310241699
Flash Point TCC Value N/a
Solubility
water, 2.811e+004 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Cheesy
cheesy, sweaty
General comment Cheesy sweaty

Safety Information

Safety information

Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
information only not used for fragrances or flavors
Recommendation for (R)-2-methyl butyric acid usage levels up to:
not for fragrance use.
Recommendation for (R)-2-methyl butyric acid flavor usage levels up to:
not for flavor use.

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :6950479
National Institute of Allergy and Infectious Diseases:Data
(2R)-2-methylbutanoic acid