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MedKoo Cat#: 558640 | Name: Isovaleric acid
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Isovaleric acid is the primary cause of the flavors added to wine caused by Brettanomyces yeasts.

Chemical Structure

Isovaleric acid
Isovaleric acid
CAS#503-74-2

Theoretical Analysis

MedKoo Cat#: 558640

Name: Isovaleric acid

CAS#: 503-74-2

Chemical Formula: C5H10O2

Exact Mass: 102.0700

Molecular Weight: 102.13

Elemental Analysis: C, 58.80; H, 9.87; O, 31.33

Price and Availability

Size Price Availability Quantity
5g USD 250.00 2 Weeks
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Related CAS #
No Data
Synonym
Isovaleric acid; Isobutyl formic acid; Isobutylformic acid; Isopentanoic acid;
IUPAC/Chemical Name
3-Methylbutanoic acid
InChi Key
GWYFCOCPABKNJV-UHFFFAOYSA-N
InChi Code
InChI=1S/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7)
SMILES Code
CC(C)CC(O)=O
Appearance
Liquid
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 102.13 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Szczesniak O, Hestad KA, Hanssen JF, Rudi K. Isovaleric acid in stool correlates with human depression. Nutr Neurosci. 2016 Sep;19(7):279-83. doi: 10.1179/1476830515Y.0000000007. Epub 2015 Feb 24. PubMed PMID: 25710209. 2: Shigematsu Y, Sudo M, Momoi T, Inoue Y, Suzuki Y, Kameyama J. Changing plasma and urinary organic acid levels in a patient with isovaleric acidemia during an attack. Pediatr Res. 1982 Sep;16(9):771-5. PubMed PMID: 7133811. 3: Arthur K, Hommes FA. Simple isotope dilution assay for propionic acid and isovaleric acid. J Chromatogr B Biomed Appl. 1995 Nov 3;673(1):132-5. PubMed PMID: 8925066. 4: Menashe I, Abaffy T, Hasin Y, Goshen S, Yahalom V, Luetje CW, Lancet D. Genetic elucidation of human hyperosmia to isovaleric acid. PLoS Biol. 2007 Oct 30;5(11):e284. PubMed PMID: 17973576; PubMed Central PMCID: PMC2043052. 5: Ackman RG. Birthweights in the Faroe Islands: possible role of isovaleric acid. J Intern Med. 1989 Feb;225(2):73-5. Review. PubMed PMID: 2646392. 6: Griff IC, Reed RR. The genetic basis for specific anosmia to isovaleric acid in the mouse. Cell. 1995 Nov 3;83(3):407-14. PubMed PMID: 8521470. 7: Thierry A, Maillard MB, Yvon M. Conversion of L-leucine to isovaleric acid by Propionibacterium freudenreichii TL 34 and ITGP23. Appl Environ Microbiol. 2002 Feb;68(2):608-15. PubMed PMID: 11823198; PubMed Central PMCID: PMC126662. 8: Loots DT, Mienie LJ, Erasmus E. Amino-acid depletion induced by abnormal amino-acid conjugation and protein restriction in isovaleric acidemia. Eur J Clin Nutr. 2007 Nov;61(11):1323-7. Epub 2007 Feb 7. PubMed PMID: 17299485. 9: Murata Y, Okutani F, Nakahira M, Ushida T, Ikemoto T, Yokoe I, Takeda T, Kaba H, Tani T, Ogawa Y. Effects of olfactory stimulation with isovaleric acid on brain activation in informed and naïve conditions: a functional MRI study. Auris Nasus Larynx. 2007 Dec;34(4):465-9. Epub 2007 May 3. PubMed PMID: 17481839. 10: ZABIN I, BLOCH K. The utilization of isovaleric acid for the synthesis of cholesterol. J Biol Chem. 1950 Jul;185(1):131-8. PubMed PMID: 15436483. 11: Britz ML, Wilkinson RG. Partial purification and characterization of two enzymes involved in isovaleric acid synthesis in Clostridium bifermentans. J Gen Microbiol. 1983 Oct;129(10):3227-37. PubMed PMID: 6655460. 12: Ribeiro CA, Balestro F, Grando V, Wajner M. Isovaleric acid reduces Na+, K+-ATPase activity in synaptic membranes from cerebral cortex of young rats. Cell Mol Neurobiol. 2007 Jun;27(4):529-40. Epub 2007 Mar 30. PubMed PMID: 17394058. 13: Pourtier L, Sicard G. Comparison of the sensitivity of C57BL/6J and AKR/J mice to airborne molecules of isovaleric acid and amyl acetate. Behav Genet. 1990 Jul;20(4):499-509. PubMed PMID: 2175173. 14: Loots DT. Abnormal tricarboxylic acid cycle metabolites in isovaleric acidaemia. J Inherit Metab Dis. 2009 Jun;32(3):403-11. doi: 10.1007/s10545-009-1071-6. Epub 2009 Apr 5. PubMed PMID: 19343532. 15: Lu R, Meng H, Gao X, Xu L, Feng X. Effect of non-surgical periodontal treatment on short chain fatty acid levels in gingival crevicular fluid of patients with generalized aggressive periodontitis. J Periodontal Res. 2014 Oct;49(5):574-83. PubMed PMID: 25340203. 16: Ribeiro CA, Leipnitz G, Amaral AU, de Bortoli G, Seminotti B, Wajner M. Creatine administration prevents Na+,K+-ATPase inhibition induced by intracerebroventricular administration of isovaleric acid in cerebral cortex of young rats. Brain Res. 2009 Mar 25;1262:81-8. doi: 10.1016/j.brainres.2009.01.005. Epub 2009 Jan 13. PubMed PMID: 19210957. 17: Koopman HN, Iverson SJ, Read AJ. High concentrations of isovaleric acid in the fats of odontocetes: variation and patterns of accumulation in blubber vs. stability in the melon. J Comp Physiol B. 2003 Apr;173(3):247-61. Epub 2003 Mar 8. PubMed PMID: 12743728. 18: Bergen BJ, Stumpf DA, Haas R, Parks JK, Eguren LA. A mechanism of toxicity of isovaleric acid in rat liver mitochondria. Biochem Med. 1982 Apr;27(2):154-60. PubMed PMID: 7082321. 19: GRISEBACH H, ACHENBACH H. [On the origin of isovaleric acid in magnamycin]. Experientia. 1963 Jan 15;19:6-7. German. PubMed PMID: 13950567. 20: Lehnert W. Excretion of N-isovalerylglutamic acid in isovaleric acidemia. Clin Chim Acta. 1981 Oct 26;116(2):249-52. PubMed PMID: 7296890.

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