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Chemistry

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Also known as: 3-methylbutanoic acid, 503-74-2, Isopentanoic acid, 3-methylbutyric acid, Delphinic acid, Butanoic acid, 3-methyl-
Molecular Formula
C5H10O2
Molecular Weight
102.13  g/mol
InChI Key
GWYFCOCPABKNJV-UHFFFAOYSA-N
FDA UNII
1BR7X184L5

Isovaleric Acid
3-Methylbutanoic acid is a metabolite found in or produced by Saccharomyces cerevisiae.
1 2D Structure

Isovaleric Acid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-methylbutanoic acid
2.1.2 InChI
InChI=1S/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7)
2.1.3 InChI Key
GWYFCOCPABKNJV-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(C)CC(=O)O
2.2 Other Identifiers
2.2.1 UNII
1BR7X184L5
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3-methylbutyrate

2. 3-methylbutyric Acid

2.3.2 Depositor-Supplied Synonyms

1. 3-methylbutanoic Acid

2. 503-74-2

3. Isopentanoic Acid

4. 3-methylbutyric Acid

5. Delphinic Acid

6. Butanoic Acid, 3-methyl-

7. Isopropylacetic Acid

8. Isovalerianic Acid

9. Isobutylformic Acid

10. 3-methylbutyrate

11. Beta-methylbutyric Acid

12. Isovalerianic

13. Acetic Acid, Isopropyl-

14. Butyric Acid, 3-methyl-

15. 3-methyl-butanoic Acid

16. Isovalerate

17. Kyselina Isovalerova

18. 3-methyl Butyric Acid

19. 3-methyl-butyric Acid

20. Fema No. 3102

21. 3-methyl-n-butyric Acid

22. Isovaleriansaeure

23. .beta.-methylbutyric Acid

24. Mfcd00002726

25. Nsc 62783

26. 3-methylbuttersaeure

27. B-methylbutyric Acid

28. 3,4-diisovaleryl Adrenaline

29. Chebi:28484

30. 1br7x184l5

31. Butanoic Acid, 3-methyl-, (r)-

32. Isopropylacetate

33. Nsc-62783

34. Iva

35. Isobutyl Formic Acid

36. Isovaleric Acid (natural)

37. Fema Number: 3102

38. Kyselina Isovalerova [czech]

39. Methyl Butanoic Acid

40. Hsdb 629

41. Einecs 207-975-3

42. Methylbutanoic Acid

43. Brn 1098522

44. Unii-1br7x184l5

45. Ai3-24132

46. B-methylbutyrate

47. Iso-valeric Acid

48. 3-methylbutanoicacid

49. Delphinic-acid

50. Iso-c4h9cooh

51. Isovaleric Acid, 99%

52. Dsstox_cid_9182

53. Bmse000373

54. Na 1760 (related)

55. Ec 207-975-3

56. Dsstox_rid_78698

57. Dsstox_gsid_29182

58. Schembl43436

59. Isovaleric Acid [mi]

60. 4-02-00-00895 (beilstein Handbook Reference)

61. Isovaleric Acid [fcc]

62. Methylbutanoic Acid (related)

63. Natural Isovaleric Acid

64. Isopropyl Acetic Acid, Natural

65. Isovaleric Acid [fhfi]

66. Isovaleric Acid [hsdb]

67. Chembl568737

68. Wln: Qv1y1&1

69. Dtxsid5029182

70. Isovaleric Acid [mart.]

71. Isovaleric Acid [who-dd]

72. Zinc388188

73. Amy40214

74. Bcp32116

75. Nsc62783

76. Str08356

77. Isovaleric Acid, Analytical Standard

78. Tox21_201604

79. Bbl027399

80. Lmfa01020181

81. S6287

82. Stl146358

83. Akos000119861

84. Isovaleric Acid, >=99%, Fcc, Fg

85. Cs-w013696

86. Db03750

87. Hy-w012980

88. 3-methylbutyric Acid: Isopropyl-acetate

89. Isovaleric Acid Sodium Salt (salt/mix)

90. Isovaleric Acid, Natural, >=98%, Fg

91. Ncgc00249082-01

92. Ncgc00259153-01

93. 35915-22-1

94. Cas-503-74-2

95. 3-methylbutyric Acid: Isopropyl-acetic Acid

96. Ft-0627533

97. M0182

98. C08262

99. D78213

100. Q415536

101. J-522594

102. F2191-0067

103. Z955123492

104. 3-methylbutanoic Acid;3-methylbutyric Acid;isopentanoic Acid

105. 92634-50-9

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 102.13 g/mol
Molecular Formula C5H10O2
XLogP31.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Exact Mass102.068079557 g/mol
Monoisotopic Mass102.068079557 g/mol
Topological Polar Surface Area37.3 Ų
Heavy Atom Count7
Formal Charge0
Complexity66.5
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 Absorption, Distribution and Excretion

It is readily absorbed from the gastrointestinal tract in man.

Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 3545


4.2 Metabolism/Metabolites

In contrast to valeric acid, isovaleric acid is ketogenic. ...Is metabolized by the liver to give two- and three-carbon fragments. The isopropyl fragment of isovaleric acid is readily converted to acetoacetate and is an efficient source of carbon atoms for fatty acid and cholesterol synthesis. Isovaleric acid ... has been identified in the fermentative organs of ruminant animals.

Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 3545


Isovaleric acid is an intermediate in leucine metabolism. High blood concentrations of isovaleric acid occur in patients with the clinical disorder "isovaleric acidemia." This is a genetic defect of leucine metabolism in which the enzyme isovaleryl-coenzyme A dehydrogenase is inhibited or absent. The disease is characterized by episodic acidosis, slight mental retardation, and an unpleasant body odor.

Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 3545


RATS RECEIVING LABELED ISOVALERIC ACID EXCRETED NONRADIOACTIVE ISOVALTHINE.

PMID:4225844 KODAMA H ET AL; ACTA MED OKAYAMA 20 (3): 107-13 (1966)


Isovalerate given iv to normal rats was rapidly metabolized, with a 50% decr in plasma concn after 11 min, and this time was shortened to 5 min by the simultaneous admin of glycine. The hypoglycin metabolite methylenecyclopropylacetate-CoA inhibited butyryl-CoA dehydrogenase and isovaleryl-CoA dehydrogenase in liver.

PMID:7317076 Al-Bassam SS, Sherratt HSA; Biochem Pharmacol 30 (20): 2817-24 (1981)


Gas chromatographic and mass spectrometric parameters of isovaleryl-beta-D-glucuronide, a new metabolite in the urine of patients with isovaleric acidemia, were presented. The significance of this metabolite for the detoxication of isovalerate in isovaleric acid media is discussed.

PMID:6652913 Dorland L et al; Clin Chim Acta 134 (1-2): 77-83 (1983)


4.3 Mechanism of Action

(14)C-LABELED ISOVALERIC ACID ADMIN ORALLY TO RATS SHOWED ISOPROPYL GROUP WAS MORE EFFICIENTLY UTILIZED FOR CHOLESTEROL SYNTH THAN CARBOXYL GROUPS, & ALSO MORE EFFICIENTLY UTILIZED THAN FATTY ACID SYNTH. CLEAVAGE OF ACID INTO 2 FRAGMENTS OCCURS BEFORE CHOLESTEROL SYNTH. (14)C-LABELED ISOVALERIC ACID ADMIN ORALLY TO RATS APPEARS TO ENHANCE THE INCORPORATION OF CARBON DIOXIDE INTO CHOLESTEROL.

PMID:4225844 KODAMA H ET AL; ACTA MED OKAYAMA 20 (3): 107-13 (1966)


All liver mitochondrial preparations were affected by 1.19 mM isovalerate. Isovaleryl CoA is a potent inhibitor of succinate:CoA ligase (SCL) with positive cooperativity and half-maximal inhibition at 273 +/-11 uM isovaleryl CoA. The investigators suggested that inhibition of the citric acid cycle at the SCL step may be a general mechanism of organic acid toxicity to mitochondria.

PMID:7082321 Bergen BJ et al; Biochem Med 27 (2): 154-60 (1982)


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Isovaleric Acid Manufacturers

A Isovaleric Acid manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Isovaleric Acid, including repackagers and relabelers. The FDA regulates Isovaleric Acid manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Isovaleric Acid API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Isovaleric Acid Suppliers

A Isovaleric Acid supplier is an individual or a company that provides Isovaleric Acid active pharmaceutical ingredient (API) or Isovaleric Acid finished formulations upon request. The Isovaleric Acid suppliers may include Isovaleric Acid API manufacturers, exporters, distributors and traders.

Isovaleric Acid GMP

Isovaleric Acid Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Isovaleric Acid GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Isovaleric Acid GMP manufacturer or Isovaleric Acid GMP API supplier for your needs.

Isovaleric Acid CoA

A Isovaleric Acid CoA (Certificate of Analysis) is a formal document that attests to Isovaleric Acid's compliance with Isovaleric Acid specifications and serves as a tool for batch-level quality control.

Isovaleric Acid CoA mostly includes findings from lab analyses of a specific batch. For each Isovaleric Acid CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Isovaleric Acid may be tested according to a variety of international standards, such as European Pharmacopoeia (Isovaleric Acid EP), Isovaleric Acid JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Isovaleric Acid USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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