28-carbon primary fatty alcohol
1-Octacosanol
Names
Preferred IUPAC name
Other names
n -Octacosanol; Octacosyl alcohol; Octanosol; Montanyl alcohol; Cluytyl alcohol
Identifiers
ChEBI
ChemSpider
ECHA InfoCard
100.008.348
KEGG
MeSH
1-octacosanol
UNII
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
OCCCCCCCCCCCCCCCCCCCCCCCCCCCC
Properties
C 28 H 58 O
Molar mass
410.771 g·mol−1
Melting point
83 °C (181 °F; 356 K)
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
1-Octacosanol [pronunciation? ] (also known as n -octacosanol, octacosyl alcohol, cluytyl[pronunciation? ] alcohol, montanyl[pronunciation? ] 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]
Octacosanol is insoluble in water but freely soluble in low molecular-weight alkanes and in chloroform .
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] In mice, octacosanol reduces stress and restores stress-affected sleep back to normal.[ 6]
^ EA Baker (1982) Chemistry and morphology of plant epicuticular waxes. pp. 139–165. 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
^ a b 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 . S2CID 43313071 .
^ 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 . PMC 4007727 . PMID 20581854 .
^ Kaushik, MK; Aritake, K; Takeuchi, A; Yanagisawa, M; Urade, Y (21 August 2017). "Octacosanol restores stress-affected sleep in mice by alleviating stress" . Scientific Reports . 7 (1): 8892. Bibcode :2017NatSR...7.8892K . doi :10.1038/s41598-017-08874-2 . PMC 5566941 . PMID 28827687 .
By consumption
Primary alcohols (1°)
Methanol Ethanol Butanol Straight-chain saturated C1 — C9 Straight-chain saturated C10 — C19 Straight-chain saturated C20 — C29 Straight-chain saturated C30 — C39
1-Triacontanol (melissyl / myricyl)
1-Hentriacontanol
1-Dotriacontanol (lacceryl)
1-Tritriacontanol
1-Tetratriacontanol (geddyl)
1-Pentatriacontanol
1-Hexatriacontanol
1-Heptatriacontanol
1-Octatriacontanol
1-Nonatriacontanol
Straight-chain saturated C40 — C49
1-Tetracontanol
1-Hentetracontanol
1-Dotetracontanol
1-Tritetracontanol
1-Tetratetracontanol
1-Pentatetracontanol
1-Hexatetracontanol
1-Heptatetracontanol
1-Octatetracontanol
1-Nonatetracontanol
Secondary alcohols (2°) Tertiary alcohols (3°) Hydric alcohols
Amyl alcohols Aromatic alcohols Saturatedfatty alcohols Branched and unsaturatedfatty alcohols Sugar alcohols
C1 — C7 Deoxy sugar alcohols Cyclic sugar alcohols Glycylglycitols
Terpene alcohols
Monoterpene alcohols Sesquiterpene alcohols Diterpene alcohols
Dialcohols Trialcohols Sterols Fluoroalcohols Preparations Reactions