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2D Structure
Also known as: 3-methylbutanal, 590-86-3, 3-methylbutyraldehyde, Isovaleral, Isopentaldehyde, Isoamylaldehyde
Molecular Formula
C5H10O
Molecular Weight
86.13  g/mol
InChI Key
YGHRJJRRZDOVPD-UHFFFAOYSA-N
FDA UNII
69931RWI96

3-methylbutanal is a metabolite found in or produced by Saccharomyces cerevisiae.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-methylbutanal
2.1.2 InChI
InChI=1S/C5H10O/c1-5(2)3-4-6/h4-5H,3H2,1-2H3
2.1.3 InChI Key
YGHRJJRRZDOVPD-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(C)CC=O
2.2 Other Identifiers
2.2.1 UNII
69931RWI96
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3-methylbutanal

2. Isopentanal

3. Isovalerylaldehyde

2.3.2 Depositor-Supplied Synonyms

1. 3-methylbutanal

2. 590-86-3

3. 3-methylbutyraldehyde

4. Isovaleral

5. Isopentaldehyde

6. Isoamylaldehyde

7. Isopentanal

8. Butanal, 3-methyl-

9. Isovalerylaldehyde

10. Isovaleric Aldehyde

11. Beta-methylbutanal

12. Isoamyl Aldehyde

13. 2-methylbutanal-4

14. 3-methyl-1-butanal

15. 1-butanal, 3-methyl-

16. Butyraldehyde, 3-methyl-

17. Iso-c4h9cho

18. Iso-valeraldehyde

19. 3-methylbutylaldehyde

20. Beta-methylbutyraldehyde

21. 3-methyl Butanal

22. Fema No. 2692

23. Butanal, Methyl-

24. 3-methyl-butanal

25. Nsc 404119

26. 3-methylbutan-1-al

27. 3-methyl Butyraldehyde

28. 3-methyl-butyraldehyde

29. Aldehyde Isovalerianique

30. Ccris 2945

31. Hsdb 628

32. 3-methylbutyraldehyde (natural)

33. Einecs 209-691-5

34. Brn 0773692

35. .beta.-methylbutanal

36. Dtxsid1021619

37. Unii-69931rwi96

38. Chebi:16638

39. Ai3-16106

40. Isovaleric-aldehyde

41. 69931rwi96

42. Nsc-404119

43. Chembl18360

44. Dtxcid201619

45. Ec 209-691-5

46. 4-01-00-03291 (beilstein Handbook Reference)

47. Mfcd00007014

48. 26140-47-6

49. Aldehyde Isovalerianique [french]

50. B-methylbutanal

51. Methyl Butanal

52. Isovaler Aldehyde

53. Isovaleraldehyde, 97%

54. Isopentanal [inci]

55. Isovaleraldehyde [mi]

56. Isovaleraldehyde [hsdb]

57. Wln: Vh1y1&1

58. 3-methyl Butanal [fcc]

59. Isovaleraldehyde, >=97%, Fg

60. Str03918

61. Isovaleraldehyde, Analytical Standard

62. Tox21_200891

63. 3-methylbutyraldehyde [fhfi]

64. Bdbm50028832

65. Nsc404119

66. Akos000118930

67. Isovaleraldehyde, Natural, >=95%, Fg

68. Ncgc00248867-01

69. Ncgc00258445-01

70. Cas-590-86-3

71. Pd124039

72. Ft-0627530

73. I0192

74. Ns00006828

75. En300-18032

76. C07329

77. Q409554

78. J-512894

79. F2190-0631

80. Inchi=1/c5h10o/c1-5(2)3-4-6/h4-5h,3h2,1-2h

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 86.13 g/mol
Molecular Formula C5H10O
XLogP31
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count2
Exact Mass g/mol
Monoisotopic Mass g/mol
Topological Polar Surface Area17.1
Heavy Atom Count6
Formal Charge0
Complexity39.2
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Metabolism/Metabolites

Aldehydes are readily oxidized to organic acids, which, in turn, can serve as substrates for fatty acid oxidation pathways and the Krebs cycle. ... Oxidation of aldehydes is catalyzed by aldehyde dehydrogenase, which has been found in the brain, erythrocytes, liver, kidney, heart, and placenta. /Aldehydes/

Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 2635


... The detoxification of aldehydes can be seen to proceed basically via two routes: (1) an oxidation to yield readily metabolized acids; (2) inactivation by reaction with sulfhydryl groups, particularly glutathione. Under conditions that either deplete glutathione levels, or that result in an inhibition of aldehyde dehydrogenase (for example, Antabuse treatment), the acute and chronic effects of aldehyde toxicity might be more fully expressed. /Aldehydes/

Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 2637


3-Methylbutanal is a volatile aldehyde which in the rat is derived, at least in part, from colonic bacterial breakdown of leucine. It has been proposed as a toxin in the pathogenesis of hepatic encephalopathy in man. The mean plasma 3-methylbutanal concentration in non-fasting patients with hepatic encephalopathy, 0.244 umol/liter (range 0-1.30) was not significantly different from the mean value in controls, 0.116 umol/liter (0-0.349). Oral leucine feeding resulted in significant increases in plasma 3-methylbutanal concentrations in both control subjects and patients with cirrhosis. Peak leucine and 3-methylbutanal values occurred at approximately the same time and usually within 120 min of leucine ingestion. Pre-treatment with neomycin had no effect on the results of leucine feeding. No changes occurred in the clinical condition or psychometric performance of patients with cirrhosis fed leucine despite increases in plasma 3-methylbutanal of up to 700% over basal values. In man plasma 3-methylbutanal, at least in part, derives from ingested leucine independently of the action of colonic bacteria.

PMID:4038637 Marshall AW et al; Clin Physiol 5 (1): 53-62 (1985)


The cytochrome P450-catalyzed formation of olefinic products from a series of xenobiotic aldehydes has been demonstrated. Isobutyraldehyde and trimethylacetaldehyde, but not propionaldehyde, are converted to the predicted olefinic products, suggesting a requirement for branching at the alpha carbon. In addition, the four C5 aldehydes of similar hydrophobicity were compared for their ability to undergo the reaction. The straight-chain valeraldehyde gave no olefinic products with five different rabbit liver microsomal P450 isozymes. However, increasing activity was seen with the other isomers in the order of isovaleraldehyde, 2-methylbutyraldehyde, and trimethylacetaldehyde, with all of the P450 cytochromes.

PMID:1924356 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC52631 Roberts ES et al; Proc Natl Acad Sci USA 88 (20): 8963-6 (1991)


4.2 Mechanism of Action

...inhibits oxidation of other mitochondrial substrates, including acetaldehyde

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V5:995


...Isovaleraldehyde is also a degradation product of leucine that is associated with hepatic encephalopathy.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V5:995