Nervonic acid

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Nervonic acid^[1]

IUPAC name (Z)-Tetracos-15-enoic acid
Other names cis-15-Tetracosenoic acid 24:1 cis, delta 9 or 24:1 omega 9
Identifiers
CAS number	506-37-6^N
PubChem	5281120
ChemSpider	4444565^Y
KEGG	C08323^Y
ChEBI	CHEBI:44247^Y
ChEMBL	CHEMBL1173379^Y
Jmol-3D images	Image 1
SMILES O=C(O)CCCCCCCCCCCCC\C=C/CCCCCCCC
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-^Y Key: GWHCXVQVJPWHRF-KTKRTIGZSA-N^Y 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
Properties
Molecular formula	C₂₄H₄₆O₂
Molar mass	366.62 g/mol
Melting point	42–43 °C
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Nervonic acid is a monounsaturated omega-9 fatty acid. Nervonic acid has been identified as important in the biosynthesis of nerve cell myelin.^[2] It is found in the sphingolipids of white matter in human brain.

Nervonic acid is used in the treatment of disorders involving demyelination, such as adrenoleukodystrophy and multiple sclerosis where there is a decreased level of nervonic acid in sphingolipids.^[3]

Notes

^ Nervonic acid at Sigma-Aldrich
^ US Patent 6664406, Nervonic acid derivatives, their preparation and use
^ WO/1996/005740, Nervonic Acid Compositions

Additional references

Appelqvist (1976) Lipids in Cruciferae. In: Vaughan JG, Macleod AJ (Eds), The biology and the Chemistry of Cruciferae. Academic Press, London, UK, pp. 221-277.
Sargent JR, Coupland K, Wilson R (1994). Nervonic Acid and Demyelinating Disease. Medical Hypothesese 42, pp. 237-242.

v t e Lipids: fatty acids

Saturated	VFA: Acetic (C2) · Propionic (C3) · Butyric (C4) · Valeric (C5) · Caproic (C6) · Enanthic (C7) · Caprylic (C8) · Pelargonic (C9) · Capric (C10) · Undecylic (C11) · Lauric (C12) · Tridecylic (C13) · Myristic (C14) · Pentadecanoic (C15) · Palmitic (C16) · Margaric (C17) · Stearic (C18) · Nonadecylic (C19) · Arachidic (C20) · Heneicosylic (C21) · Behenic (C22) · Tricosylic (C23) · Lignoceric (C24) · Pentacosylic (C25) · Cerotic (C26) · Heptacosylic (C27) · Montanic (C28) · Nonacosylic (C29) · Melissic (C30) · Hentriacontylic (C31) · Lacceroic (C32) · Psyllic (C33) · Geddic (C34) · Ceroplastic (C35) · Hexatriacontylic (C36)

n−3 Unsaturated	α-Linolenic • Stearidonic • Eicosapentaenoic • Docosahexaenoic

n−6 Unsaturated	Linoleic • γ-Linolenic • Dihomo-γ-linolenic • Arachidonic

n−9 Unsaturated	Oleic • Elaidic • Eicosenoic • Erucic • Nervonic • Mead

biochemical families: proteins (amino acids/intermediates) · nucleic acids (constituents/intermediates) · carbohydrates (glycoproteins, alcohols, glycosides) lipids (fatty acids/intermediates, phospholipids, steroids, sphingolipids, eicosanoids) · tetrapyrroles/intermediates

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