Isovaleric acid

Base Information

• Chemical Name: Isovaleric acid
• CAS No.: 503-74-2
• Molecular Formula: C5H10O2
• Molecular Weight: 102.133
• Hs Code.: 2915 60 90
• European Community (EC) Number: 207-975-3
• NSC Number: 62783
• UN Number: 2810,1760
• UNII: 1BR7X184L5
• DSSTox Substance ID: DTXSID5029182
• Nikkaji Number: J2.605K
• Wikidata: Q415536
• Metabolomics Workbench ID: 246
• ChEMBL ID: CHEMBL568737
• Mol file: 503-74-2.mol

Synonyms:3-methylbutyrate;3-methylbutyric acid;isovaleric acid

Chemical Property of Isovaleric acid

Chemical Property:

• Appearance/Colour: colorless to yellowish transparent liquid.
• Vapor Pressure: 0.38 mm Hg ( 20 °C)
• Melting Point: -35 °C
• Refractive Index: n20/D 1.403(lit.)
• Boiling Point: 175.295 °C at 760 mmHg
• PKA: 4.77(at 25℃)
• Flash Point: 73.402 °C
• PSA: 37.30000
• Density: 0.963 g/cm³
• LogP: 1.11710
• Storage Temp.: Store below +30°C.
• Solubility.: 48g/l
• Water Solubility.: 25 g/L (20 ºC)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 102.068079557
• Heavy Atom Count: 7
• Complexity: 66.5
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Isovaleric Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,T
• Hazard Codes: C,T
• Statements: 34-24-22
• Safety Statements: 26-36/37/39-45-38-28A

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: CC(C)CC(=O)O
• Recent ClinicalTrials: Study to Evaluate Elexacaftor/Tezacaftor/Ivacaftor (ELX/TEZ/IVA) Long-term Safety and Efficacy in Subjects Without F508del
• Recent EU Clinical Trials: A Phase 3 Study Evaluating the Pharmacokinetics, Safety, and Tolerability of VX-121/Tezacaftor/Deutivacaftor Triple Combination Therapy in Cystic Fibrosis Subjects 1 Through 11 Years of Age
• Description: Isovaleric acid has a characteristic disagreeable odor. It is extremely penetrating and persistent with a sour taste. May be synthesized by oxidation of isoamyl alcohol or isovaleric aldehyde.
• Uses: Isovaleric acid is used extensively as a flavoring ingredient in nonalcoholic beverages and in foods such as ice cream, candy, baked goods, and cheese, as a fragrance ingredient in perfumes, and as a chemical intermediate in the manufacture of sedatives and other pharmaceutical products. It is also used as an extractant of mercaptans from petroleum hydrocarbons, a vinyl stabilizer, and as an intermediate in the manufacture of plasticizers and synthetic lubricants. A molecular entity capable of donating a hydron to an acceptor (Bronsted base). It is a favorable carbon source for cell growth. Moreover, it is a promising odor indicator. In flavors, perfumes, manufacture of sedatives.

Technology Process of Isovaleric acid

There total 301 articles about Isovaleric 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: 99.1%

isovaleraldehyde (590-86-3) → 3-methylbutyric acid (503-74-2)

Guidance literature:

With potassium acetate; palladium diacetate; C₃₄H₃₆O₈; at 30 - 35 ℃; for 6h; Reagent/catalyst; Catalytic behavior; Inert atmosphere;

Reference yield: 95.0%

4-methyl-2-pentanone (108-10-1) → 3-methylbutyric acid (503-74-2)

Guidance literature:

With sodium hydroxide; sodium bromite; sodium bromide; In water; at 0 ℃; for 12h;

Reference yield: 93.0%

3-Methylbutenoic acid (541-47-9) → 3-methylbutyric acid (503-74-2)

Guidance literature:

With nickel; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1055/s-1999-2908

upstream raw materials:

4,4-dimethyloxetan-2-one

2-iodo-propane

sodium ethyl acetylacetate enolate

tetrachloromethane

Downstream raw materials:

3-methyl-1-(o-tolyl)butan-1-one

methyl 3-methylbutanoate

propyl isovalerate

4-Methyl-1-phenyl-2-pentanone

Refernces

• 1、 Bohlmann, Ferdinand,Grenz, Michael,Dahr, Autar K.,Goodman, Mark. "LABDANE DERIVATIVES AND FLAVONES FROM GUTIERREZIA DRACUNCULOIDES". . p. 105 - 108. Retrieved 1981.
• 2、 Chen, Liang-Yu,Hu, Anren,Chang, Chih-Jui. "The degradation mechanism of toxic atractyloside in herbal medicines by decoction". . p. 2018 - 2028. Retrieved 2013.
• 3、 Ono, Masateru,Oda, Satoko,Yasuda, Shin,Mineno, Tomoko,Okawa, Masafumi,Kinjo, Junei,Miyashita, Hiroyuki,Yoshimitsu, Hitoshi,Nohara, Toshihiro,Miyahara, Kazumoto. "Acylated glycosidic acid methyl esters generated from the convolvulin fraction of Rhizoma Jalapae Braziliensis by treatment with indium(III) chloride in methanol". . p. 107 - 111. Retrieved 2017.
• 4、 Calderon, J. S.,Quijano, L.,Garduno, M.,Gomez, F.,Rios, T.. "2α-ISO-VALEROYLOXYEPERUIC ACID, A DITERPENE FROM EUPATORIUM PETIOLARE". . p. 2617 - 2619. Retrieved 1983.
• 5、 Billeter,Miescher. "". . p. 564,569. Retrieved 1949.
• 6、 Irie et al.. "". . p. 678. Retrieved 1967.
• 7、 -. "Method for preparing isovaleric acid, ligand and complex in catalytic system of isovaleric acid, and application of catalytic system". Paragraph 0087-0111. . Retrieved 2020/02/29.
• 8、 Song, Tao,Ma, Zhiming,Yang, Yong. "Chemoselective Hydrogenation of α,β-Unsaturated Carbonyls Catalyzed by Biomass-Derived Cobalt Nanoparticles in Water". . p. 1313 - 1319. Retrieved 2019/01/25.