Nervonic acid

Nervonic acid[1]
Names
IUPAC name
(Z)-Tetracos-15-enoic acid
Other names
cis-15-Tetracosenoic acid
24:1 cis, delta 15 or 24:1 omega 9
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.108.655 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C24H46O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h9-10H,2-8,11-23H2,1H3,(H,25,26)/b10-9- checkY
    Key: GWHCXVQVJPWHRF-KTKRTIGZSA-N checkY
  • InChI=1/C24H46O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h9-10H,2-8,11-23H2,1H3,(H,25,26)/b10-9-
    Key: GWHCXVQVJPWHRF-KTKRTIGZBL
  • O=C(O)CCCCCCCCCCCCC\C=C/CCCCCCCC
Properties
C24H46O2
Molar mass 366.62 g/mol
Melting point 42 to 43 °C (108 to 109 °F; 315 to 316 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Nervonic acid (24:1, n−9) is a fatty acid. It is a monounsaturated analog of lignoceric acid (24:0). It is also known as selacholeic acid and cis-15-tetracosenoic acid. Its name derives from the Latin word nervus, meaning nerve or sinew.

It exists in nature as an elongation product of oleic acid (18:1 Δ9). Its immediate precursor is erucic acid. Nervonic acid is particularly abundant in the white matter of animal brains and in peripheral nervous tissue where nervonyl sphingolipids are enriched in the myelin sheath of nerve fibers.[2]

This acid is among the group of cerebrosides, which are fatty acids of the glycosphingolipids group, which are components of muscles and the nervous system, accounting for approximately 40% of the total fatty acids in sphingolipids.[3]

  1. ^ Nervonic acid at Sigma-Aldrich
  2. ^ "American Oil Chemists' Society". AOCS. Archived from the original on 2016-03-04.
  3. ^ Sandhir, R.; Khan, M.; Chahal, A.; Singh, I. (1998). "Localization of nervonic acid beta-oxidation in human and rodent peroxisomes: Impaired oxidation in Zellweger syndrome and X-linked adrenoleukodystrophy" (PDF). Journal of Lipid Research. 39 (11): 2161–71. doi:10.1016/S0022-2275(20)32471-8. PMID 9799802.