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Chemistry

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Also known as: Caprylic acid, 124-07-2, N-octanoic acid, Octylic acid, N-caprylic acid, Octoic acid
Molecular Formula
C8H16O2
Molecular Weight
144.21  g/mol
InChI Key
WWZKQHOCKIZLMA-UHFFFAOYSA-N
FDA UNII
OBL58JN025

Caprylic Acid
Caprylic acid is a metabolite found in the aging mouse brain.
1 2D Structure

Caprylic Acid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
octanoic acid
2.1.2 InChI
InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)
2.1.3 InChI Key
WWZKQHOCKIZLMA-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCCCCC(=O)O
2.2 Other Identifiers
2.2.1 UNII
OBL58JN025
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Caprylic Acid

2. Caprylic Acid, 14c-labeled

3. Caprylic Acid, Aluminum Salt

4. Caprylic Acid, Ammonia Salt

5. Caprylic Acid, Barium Salt

6. Caprylic Acid, Cadmium Salt

7. Caprylic Acid, Calcium Salt

8. Caprylic Acid, Cesium Salt

9. Caprylic Acid, Chromium(+2) Salt

10. Caprylic Acid, Cobalt Salt

11. Caprylic Acid, Copper Salt

12. Caprylic Acid, Copper(+2) Salt

13. Caprylic Acid, Iridum(+3) Salt

14. Caprylic Acid, Iron(+3) Salt

15. Caprylic Acid, Lanthanum(+3) Salt

16. Caprylic Acid, Lead(+2) Salt

17. Caprylic Acid, Lithium Salt

18. Caprylic Acid, Manganese Salt

19. Caprylic Acid, Nickel(+2) Salt

20. Caprylic Acid, Potassium Salt

21. Caprylic Acid, Ruthenium(+3) Salt

22. Caprylic Acid, Sodium Salt

23. Caprylic Acid, Sodium Salt, 11c-labeled

24. Caprylic Acid, Tin Salt

25. Caprylic Acid, Tin(+2) Salt

26. Caprylic Acid, Zinc Salt

27. Caprylic Acid, Zirconium Salt

28. Caprylic Acid, Zirconium(+4) Salt

29. Lithium Octanoate

30. Octanoate

31. Sodium Caprylate

32. Sodium Octanoate

2.3.2 Depositor-Supplied Synonyms

1. Caprylic Acid

2. 124-07-2

3. N-octanoic Acid

4. Octylic Acid

5. N-caprylic Acid

6. Octoic Acid

7. N-octylic Acid

8. N-octoic Acid

9. 1-heptanecarboxylic Acid

10. Neo-fat 8

11. Enantic Acid

12. Octic Acid

13. C-8 Acid

14. Fema No. 2799

15. Kaprylsaeure

16. Hexacid 898

17. Acido Octanoico

18. Acide Octanoique

19. 1-octanoic Acid

20. Acidum Octanocium

21. Fatty Acids, C6-10

22. Kyselina Kaprylova

23. Capryloate

24. C8:0

25. Octylate

26. Octansaeure

27. Nsc 5024

28. Nsc-5024

29. Octanoic Acid (caprylic Acid)

30. Kortacid-0899

31. Chebi:28837

32. Emery 657

33. Prifac 2901

34. Prifac-2901

35. Lunac 8-95

36. Edenor C 8-98-100

37. Ch3-[ch2]6-cooh

38. Obl58jn025

39. Caprylsaeure

40. Nsc5024

41. N-caprylate

42. N-octoate

43. N-octylate

44. Caprylic Acid (nf)

45. 68937-74-6

46. Ncgc00090957-01

47. Octanoic Acid (usan)

48. 0ctanoic Acid

49. 1-heptanecarboxylate

50. Dsstox_cid_1645

51. Caprylic Acid [nf]

52. Dsstox_rid_76259

53. Dsstox_gsid_21645

54. Octanoic Acid [usan]

55. Caprylic Acid (natural)

56. Acide Octanoique [french]

57. Acido Octanoico [spanish]

58. Acidum Octanocium [latin]

59. Kyselina Kaprylova [czech]

60. Octanoic Acid [usan:inn]

61. 287111-06-2

62. Cas-124-07-2

63. Acid C8

64. Ccris 4689

65. Hsdb 821

66. Einecs 204-677-5

67. Mfcd00004429

68. Brn 1747180

69. Unii-obl58jn025

70. Caprylic-acid

71. N-octanoicacid

72. Octanic Acid

73. Ai3-04162

74. Acidum Octanoicum

75. Einecs 273-085-7

76. Kortacid 0899

77. Neo-fat 8s

78. Caprylic Acid 657

79. N-heptanecarboxylic Acid

80. Fatty Acids, C6-1o

81. Lunac 8-98

82. Heptane-1-carboxylic Acid

83. Octanoic Acid, >=98%

84. Octanoic Acid, >=99%

85. Bmse000502

86. Caprylic/capric Acid Blend

87. Ec 204-677-5

88. Octanoic Acid-2-[13c]

89. Caprylic Acid [mi]

90. Octanoic Acid [ii]

91. Schembl3933

92. Wln: Qv7

93. Nciopen2_002902

94. Nciopen2_009358

95. Octanoic Acid (usan/inn)

96. Octanoic Acid [inn]

97. Caprylic Acid [inci]

98. Octanoic Acid [fhfi]

99. Octanoic Acid [hsdb]

100. 4-02-00-00982 (beilstein Handbook Reference)

101. Mls002415762

102. Octanoic Acid, >=96.0%

103. Caprylic Acid (octanoic Acid)

104. Caprylic Acid [vandf]

105. Octanoic Acid (mixed Isomers)

106. Octanoic Acid [mart.]

107. Chembl324846

108. Gtpl4585

109. Octanoic Acid, >=98%, Fg

110. Qspl 011

111. Qspl 184

112. Caprylic Acid [usp-rs]

113. Octanoic Acid [who-dd]

114. Dtxsid3021645

115. Octanoic Acid-1,2-[13c2]

116. Octanoic Acid-7,8-[13c2]

117. Hms2270a23

118. Octanoic Acid, Analytical Standard

119. Caprylic Acid [ep Impurity]

120. Str10050

121. Zinc1530416

122. Tox21_111045

123. Tox21_201279

124. Tox21_300345

125. Bdbm50485608

126. Caprylic Acid [ep Monograph]

127. Lmfa01010008

128. S6296

129. Stl282742

130. Akos000118802

131. Octanoic Acid, Natural, >=98%, Fg

132. Db04519

133. Fa(8:0)

134. Octanoic Acid, For Synthesis, 99.5%

135. Ncgc00090957-02

136. Ncgc00090957-03

137. Ncgc00090957-04

138. Ncgc00090957-05

139. Ncgc00254446-01

140. Ncgc00258831-01

141. Bp-27909

142. Hy-41417

143. Smr001252279

144. Cs-0016549

145. Ft-0660765

146. O0027

147. Octanoic Acid 100 Microg/ml In Acetonitrile

148. C06423

149. D05220

150. Q409564

151. Sr-01000865607

152. J-005040

153. Sr-01000865607-2

154. Brd-k35170555-001-07-9

155. Z955123584

156. Caprylic Acid (constituent Of Saw Palmetto) [dsc]

157. Octanoic Acid, Certified Reference Material, Tracecert(r)

158. 43fda9d7-2300-41e7-a373-a34f25b81553

159. Caprylic Acid, European Pharmacopoeia (ep) Reference Standard

160. Caprylic Acid, United States Pharmacopeia (usp) Reference Standard

161. Caprylic Acid (octanoic Acid), Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 144.21 g/mol
Molecular Formula C8H16O2
XLogP33
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count6
Exact Mass144.115029749 g/mol
Monoisotopic Mass144.115029749 g/mol
Topological Polar Surface Area37.3 Ų
Heavy Atom Count10
Formal Charge0
Complexity89.3
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Exptl Use: A simple methodology for hyperimmune horse plasma fractionation, based on caprylic acid precipitation, is described. Optimal conditions for fractionation were studied; the method gives best results when concentrated caprylic acid was added to plasma, whose pH had been adjusted to 5.8, until a final caprylic acid concentration of 5% was reached. The mixture was vigorously stirred during caprylic acid addition and then for 60 min; afterwards the mixture was filtered. Non-immunoglobulin proteins precipitated in these conditions, whereas a highly enriched immunoglobulin preparation was obtained in the filtrate, which was then dialysed to remove caprylic acid before the addition of sodium chloride and phenol. Thus, antivenon was produced after a single precipitation step followed by dialysis. In order to compare this methodology with that based on ammonium sulfate fractionation, a sample of hyperimmune plasma was divided into two aliquots which were fractionated in parallel by both methods. It was found that caprylic acid-fractionated antivenom was superior in terms of yield, production time, albumin/globulin ratio, turbidity, protein aggregates, electrophoretic pattern and neutralizing potency against several activities of Bothrops asper venom. Owing to its efficacy and simplicity, this method could be of great value in antivenom and antitoxin production laboratories.

PMID:8016856 Rojas G et al; Toxicon 32 (3): 351-63 (1994)


/EXPL THER/ The treatment for patients with genetic disorders of mitochondrial long-chain fatty acid beta-oxidation is directed toward providing sufficient sources of energy for normal growth and development, and at the same time preventing the adverse effects that precipitate or result from metabolic decompensation. Standard of care treatment has focused on preventing the mobilization of lipids that result from fasting and providing medium-chain triglycerides (MCT) in the diet in order to bypass the long-chain metabolic block. MCTs that are currently available as commercial preparations are in the form of even-chain fatty acids that are predominately a mixture of octanoate and decanoate ... The even-numbered medium-chain fatty acids (MCFAs) that are found in MCT preparations can reduce the accumulation of potentially toxic long-chain metabolites of fatty acid oxidation (FAO) ... /Octanoate/

PMID:14741189 Jones PM et al; Mol Genet Metab 81(2):96-9 (2004)


Children who suffer from seizures which are not controllable by drugs have apparently been successfully treated with MCT (medium chain triglyceride) diet. The MCT diet is an emulsion containing primarily (81%) octanoic acid, but also contains 15% decanoic acid ... /Medium chain triglyceride/

European Chemicals Bureau; IUCLID Dataset, Decanoic acid (CAS #334-48-5) p.45 (2000 CD-ROM edition). Available from, as of January 23, 2008: https://esis.jrc.ec.europa.eu/


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

Children who suffer from seizures which are not controllable by drugs have apparently been successfully treated with MCT (medium chain triglyceride) diet. The MCT diet is an emulsion containing primarily (81%) octanoic acid, but also contains 15% decanoic acid. In this study 15 children were receiving 50 to 60% of their energy requirement s from the MCT emulsion. Blood samples were analyzed for decanoic and octanoic acid levels. There was a wide variation in absolute levels, possibly due to poor patient compliance, but all patients showed low levels in the mornings, rising to high levels in the evenings. This suggested that both acids are rapidly metabolized. /Medium chain triglyceride/

European Chemicals Bureau; IUCLID Dataset, Decanoic acid (CAS #334-48-5) p.45 (2000 CD-ROM edition). Available from, as of January 23, 2008: https://esis.jrc.ec.europa.eu/


To assess the disposition kinetics of selected structural analogs of valproic acid, the pharmacokinetics of valproic acid and 3 structural analogs, cyclohexanecarboxylic acid, l-methyl-l-cyclohexanecarboxylic acid (1-methylcyclohexanecarboxylic acid; and octanoic acid were examined in female rats. All 4 carboxylic acids evidenced dose-dependent disposition. A dose-related decrease in total body clearance was observed for each compound, suggesting saturable eiminination processes. The apparent volume of distribution for these compounds was, with the exception of cyclohexanecarboxylic acid, dose-dependent, indicating that binding to proteins in serum and/or tissues may be saturable. Both valproic acid and 1-methylcyclohexanecarboxylic acid exhibited enterohepatic recirculation, which appeared to be dose- and compound-dependent. Significant quantities of both valproic acid and 1-methylcyclohexanecarboxylic acid were excreted in the urine as conjugates. Octanoic acid and cyclohexanecarboxylic acid were not excreted in the urine and did not evidence enterohepatic recirculation. It was concluded that minor changes in chemical structure of low molecular weight carboxylic acids have an influence on their metabolism and disposition.

PMID:8499583 Liu MJ, Pollack GM; Biopharm Drug Dispos 14 (May): 325-39 (1993)


5.2 Metabolism/Metabolites

Caprylic acid administered to rats is readily metabolized by the liver and many other tissues, forming carbon dioxide and two-carbon fragments, which are incorporated into long-chain fatty acids, as well as other water-soluble products.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 726


5.3 Mechanism of Action

Mitochondrial uncoupling is often invoked as a mechanism underlying cellular dysfunction; however, it has not been possible to study this phenomenon directly in intact cells and tissues. In this paper ... direct evaluation of mitochondrial uncoupling in the intact myocardium using (31)P NMR magnetization transfer techniques /are reported/. Langendorff perfused rat hearts were exposed to either a known uncoupler, 2,4-dinitrophenol, or a potential uncoupler, octanoate. Both 2,4-dinitrophenol and octanoate decreased mechanical function as measured by the rate pressure product and caused an increase in the oxygen consumption rate; with 2,4-dinitrophenol this increase in oxygen consumption rate was dose-dependent. The ATP synthesis rate measured by (31)P NMR, however, was not elevated commensurately with oxygen consumption rate; instead, the P/O ratio declined. In contrast, the linear relationship between the ATP synthesis rate and rate pressure product was not altered by the uncoupling agents. These data demonstrate that 1) (31)P NMR magnetization transfer can be utilized to measure uncoupling of oxidative phosphorylation in intact organs, 2) octanoate does not induce excess ATP utilization in the intact heart, and 3) high levels of octanoate induce mitochondrial uncoupling in the intact myocardium; and this may, in part, be the cause of the toxic effects associated with fatty acid exposure. /Octanoate/

PMID:2136855 Kingsley-Hickman PB et al; J Biol Chem 265 (3): 1545-50 (1990)


It has been shown that polyunsaturated fatty acids such as arachidonic and docosahexanoic acids but not monounsaturated and saturated long-chain fatty acids promote basal and nerve growth factor (NGF)-induced neurite extension of PC12 cells, a line derived from a rat pheochromocytoma. On the other hand, short-chain fatty acids and valproic acid (2-propylpentanoic acid) enhance the growth of neurite processes of the cells only in the presence of inducers. In this study, /investigators/ demonstrated that straight medium-chain fatty acids (MCFAs) at millimolar concentrations alone potently induced neuronal differentiation of PC12 cells. ... Nonanoic, decanoic, and dodecanoic acids also induced growth of neurite processes, but their maximal effects were less marked than that of octanoic acid. ...

PMID:17434686 Kamata Y et al; Neuroscience 146 (3): 1073-81 (2007)


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22-Jan-2021
29-Aug-2024
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