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Nervonic acid information


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
CAS Number
  • 506-37-6 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:44247 checkY
ChEMBL
  • ChEMBL1173379 checkY
ChemSpider
  • 4444565 checkY
ECHA InfoCard 100.108.655 Edit this at Wikidata
KEGG
  • C08323 checkY
PubChem CID
  • 5281120
UNII
  • 91OQS788BE checkY
CompTox Dashboard (EPA)
  • DTXSID801009308 Edit this at Wikidata
InChI
  • 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
SMILES
  • O=C(O)CCCCCCCCCCCCC\C=C/CCCCCCCC
Properties
Chemical formula
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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Infobox references

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.

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Nervonic acid

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acid (3.5–4.5%), oleic acid (16–20%), linoleic acid (35–38%), eicosenoic acid (3.5–5.5%), erucic acid (1.5–3.5%), and nervonic acid (1.5%). The oil is often...

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its seed has the highest-known proportion of nervonic acid (C24H46O2, PubChem CID: 5281120). Nervonic acid is an important component in myelin biosynthesis...

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Very long chain fatty acid

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ceroplastic acid (C35). Several monounsaturated VLCFAs are also known: nervonic acid (Δ15-24:1), ximenic acid (Δ17-26:1), and lumequeic acid (Δ21-30:1)...

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Xanthoceras

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oil. The oil is particularly rich in long chain fatty acids, including erucic and nervonic acid, making it suitable for certain industrial purposes. Illipe...

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(August 2020). "The Acer truncatum genome provides insights into the nervonic acid biosynthesis". The Plant Journal. 104 (3): 662–678. doi:10.1111/tpj...

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Ximenia americana

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linoleic, and stearic acids along with smaller amounts of lumequic, ximenynic acid, arachidonic, erucic, and nervonic acids and a variety of other compounds...

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Heliophila africana

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acids. Linoleic acid makes up around 22% of the seed fatty acids. The relatively high levels of nervonic acid and lower levels of erucic acid may make this...

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