1-Octacosanol

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1-Octacosanol

IUPAC name Octacosan-1-ol
Other names n-Octacosanol; Octacosyl alcohol; Octanosol; Montanyl alcohol; Cluytyl alcohol
Identifiers
CAS number	557-61-9^N
PubChem	68406
ChemSpider	61689^Y
UNII	81I2215OVK^Y
KEGG	C08387^Y
MeSH	1-octacosanol
ChEBI	CHEBI:28243^Y
Jmol-3D images	Image 1
SMILES OCCCCCCCCCCCCCCCCCCCCCCCCCCCC
InChI InChI=1S/C28H58O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29/h29H,2-28H2,1H3^Y Key: CNNRPFQICPFDPO-UHFFFAOYSA-N^Y InChI=1/C28H58O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29/h29H,2-28H2,1H3 Key: CNNRPFQICPFDPO-UHFFFAOYAC
Properties
Molecular formula	C₂₈H₅₈O
Molar mass	410.76 g mol⁻¹
Melting point	83 °C; 181 °F; 356 K
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

1-Octacosanol (also known as n-octacosanol, octacosyl alcohol, cluytyl alcohol, montanyl alcohol) is a straight-chain aliphatic 28-carbon primary fatty alcohol that is common in the epicuticular waxes of plants, including the leaves of many species of Eucalyptus, of most forage and cereal grasses, of Acacia, Trifolium, Pisum and many other legume genera among many others, sometimes as the major wax constituent.^[1] Octacosanol also occurs in wheat germ.^[2]

Chemistry

Octacosanol is insoluble in water but freely soluble in low molecular-weight alkanes and in chloroform.

Biological effects

Octacosanol is the main component in the mixture policosanol.^[3] Octacosanol has been subject to preliminary study for its potential benefit for patients with Parkinson's disease.^[4]^[5] Studies have also found that octacosanol may inhibit the production of cholesterol.^[3]

References

↑ EA Baker (1982) Chemistry and morphology of plant epicuticular waxes. pp139-165. In "The Plant Cuticle". edited by DF Cutler, KL Alvin and CE Price. Academic Press, London. ISBN 0-12-199920-3
↑ "Octacosanol". Natural Products (Professional). drugs.com. Archived from the original on 3 June 2009. Retrieved 9 July 2009. "isolated from wheat germ oil or other plants"
↑ 3.0 3.1 Taylor, Johanna C; Rapport, Lisa; Lockwood, G.Brian (2003). "Octacosanol in human health". Nutrition 19 (2): 192–5. doi:10.1016/S0899-9007(02)00869-9. PMID 12591561.
↑ Snider, SR (1984). "Octacosanol in parkinsonism". Annals of neurology 16 (6): 723. doi:10.1002/ana.410160615. PMID 6395790.
↑ Wang, T; Liu, YY; Wang, X; Yang, N; Zhu, HB; Zuo, PP (2010). "Protective effects of octacosanol on 6-hydroxydopamine-induced Parkinsonism in rats via regulation of ProNGF and NGF signaling". Acta pharmacologica Sinica 31 (7): 765–74. doi:10.1038/aps.2010.69. PMID 20581854.

v t e Alcohols

Straight-chain primary alcohols (1°)	Methanol (C 1) Ethanol (C 2) 1-Propanol (C 3) n-Butanol (C 4) 1-Pentanol (C 5) 1-Hexanol (C 6) 1-Heptanol (C 7) 1-Octanol (C 8) 1-Nonanol (C 9) 1-Decanol (C 10) Undecanol (C 11) Dodecanol (C 12) Tridecan-1-ol (C 13) 1-Tetradecanol (C 14) Pentadecan-1-ol (C 15) Cetyl alcohol (C 16) Heptadecan-1-ol (C 17) Stearyl alcohol (C 18) Nonadecan-1-ol (C 19) Arachidyl alcohol (C 20) Heneicosan-1-ol (C 21) Docosanol (C 22) Tricosan-1-ol (C 23) 1-Tetracosanol (C 24) Pentacosan-1-ol (C 25) 1-Hexacosanol (C 26) 1-Heptacosanol (C 27) 1-Octacosanol (C 28) 1-Nonacosanol (C 29) Triacontanol (C 30) Policosanol

Other primary alcohols	Isobutanol (C 4) Isoamyl alcohol (C 5)

Secondary alcohols (2°)	Isopropanol (C 3) 2-Butanol (C 4) 2-Pentanol (C 5) 2-Hexanol (C 6) 2-Heptanol (C 7) 2-Methyl-1-butanol (C 5) Cyclohexanol (C 6)

Tertiary alcohols (3°)	tert-Butyl alcohol (C 4) tert-Amyl alcohol (C 5) 2-Methyl-2-pentanol (C 6) 2-Methylhexan-2-ol (C 7) 2-Methylheptan-2-ol (C 8) 3-Methyl-3-pentanol (C 6) 3-Methyloctan-3-ol (C 9)

Biochemical families: carbohydrates alcohols glycoproteins glycosides lipids eicosanoids fatty acids / intermediates phospholipids sphingolipids steroids nucleic acids constituents / intermediates proteins Amino acids / intermediates tetrapyrroles / intermediates

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