3-Methylvaleric acid

Base Information

• Chemical Name: 3-Methylvaleric acid
• CAS No.: 105-43-1
• Deprecated CAS: 22160-40-3
• Molecular Formula: C₆H₁₂O₂
• Molecular Weight: 116.16
• Hs Code.: 29159080
• European Community (EC) Number: 203-297-7
• UNII: 85FS4Y39LJ
• DSSTox Substance ID: DTXSID20861716
• Nikkaji Number: J95.910C
• Wikidata: Q27269640
• Metabolomics Workbench ID: 145
• ChEMBL ID: CHEMBL1789215
• Mol file: 105-43-1.mol

Synonyms:3-methylvalerate;3-methylvaleric acid

Chemical Property of 3-Methylvaleric acid

Chemical Property:

• Appearance/Colour: COA
• Vapor Pressure: 0.147mmHg at 25°C
• Melting Point: -41 °C
• Refractive Index: n20/D 1.416(lit.)
• Boiling Point: 199 °C at 760 mmHg
• PKA: pK1:4.766 (25°C)
• Flash Point: 88.4 °C
• PSA: 37.30000
• Density: 0.928 g/cm³
• LogP: 1.50720
• Storage Temp.: Store below +30°C.
• Water Solubility.: insoluble
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 116.083729621
• Heavy Atom Count: 8
• Complexity: 78.6

Purity/Quality:

99.9% ^*data from raw suppliers

3-Methylvaleric Acid >98.0%(GC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC(C)CC(=O)O
• Chemical Composition and Structure: 3-Methylvaleric acid, also known as 3-methylpentanoic acid or 3-methyl-N-valeric acid, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. It's chemical structure consists of a five-carbon chain with a methyl group attached to the third carbon atom, forming a branch.
• Sources: 3-Methylvaleric acid can be found in essential oils derived from plants like Valeriana jatamansi and Valeriana wallichii.
• Uses and Mechanism of Action: 3-Methylvaleric acid and its derivatives have insecticidal properties and are potential candidates for the development of natural insecticides or fumigants for controlling insects in stored grains. Additionally, it has been traditionally used as a medicinal herb for the treatment of sleep disorders, nervous disorders, and obesity. Commercially, it is used in various drugs, perfumes, and flavorings. Insecticidal activity against booklice has been demonstrated, with 3-Methylvaleric acid exhibiting contact and fumigant toxicities. It acts by inducing toxicity against stored grain insects, potentially through mechanisms that disrupt their physiological processes.
• Production Methods: 3-Methylvaleric acid can be obtained from natural sources like Valeriana jatamansi and Valeriana wallichii through extraction processes or synthesized chemically for commercial use. In nature, microbial strategies for the metabolism of 3-methylvaleric acid have been studied, demonstrating various pathways employed by bacteria for its degradation.

Technology Process of 3-Methylvaleric acid

There total 61 articles about 3-Methylvaleric acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

sec-butylethynyl tosylate (104808-01-7) → 3-methylvaleric acid (105-43-1,22160-40-3)

Guidance literature:

With hydrogenchloride; In acetonitrile; for 24h; Heating;

DOI:10.1021/jo00232a028

Reference yield: 84.0%

3-methyl-1-pentanol (589-35-5,20281-83-8) → 3-methylvaleric acid (105-43-1,22160-40-3)

Guidance literature:

3-methyl-1-pentanol; With [RuCl₂(p-cymene)(iPr₂-imy)]; tricyclohexylphosphine tetrafluoroborate; potassium hydroxide; In toluene; for 18h; Schlenk technique; Inert atmosphere; Reflux;

With hydrogenchloride; In water; pH=1;

DOI:10.1021/acs.joc.6b02105

Reference yield:

4,5-dimethylfuran-2-(3H)-one (108939-85-1) → dihydro-4-methyl-2(3H)-furanone (64190-48-3,65284-00-6,70470-05-2,1679-49-8) + 3-methylvaleric acid (105-43-1,22160-40-3)

Guidance literature:

With platinum(IV) oxide; ethanol; Hydrogenation;

upstream raw materials:

4,5-dimethylfuran-2-(3H)-one

sec-butyl-malonic acid diethyl ester

1-bromo-2-methyl-butane

4-methylisovaleramide

Downstream raw materials:

2,3-dimethyl-butanoic acid, ethyl ester

2,3-dimethylbutyryl chloride

(R)-3-methylpentanoic acid

2,3-dimethyl-N-phenylbutanamide

Refernces

• 1、 Johns, Lesley,Belt, Simon,Lewis, C. Anthony,Rowland, Steven,Masse, Guillaume,Robert, Jean-Michel,Koenig, Wilfried A.. "Configurations of polyunsaturated sesterterpenoids from the diatom, Haslea ostrearia". . p. 607 - 611. Retrieved 2000.
• 2、 Wotiz et al.. "-". . p. 6342. Retrieved 1953.
• 3、 Santilli, Carola,Makarov, Ilya S.,Fristrup, Peter,Madsen, Robert. "Dehydrogenative Synthesis of Carboxylic Acids from Primary Alcohols and Hydroxide Catalyzed by a Ruthenium N-Heterocyclic Carbene Complex". . p. 9931 - 9938. Retrieved 2016/11/02.
• 4、 Yabuuchi, Tetsuya,Kusumi, Takenori. "Phenylglycine methyl ester, a useful tool for absolute configuration determination of various chiral carboxylic acids". . p. 397 - 404. Retrieved 2007/10/03.