1-Octacosanol

1-Octacosanol
Names
	IUPAC name Octacosan-1-ol
	Other names n-Octacosanol; Octacosyl alcohol; Octanosol; Montanyl alcohol; Cluytyl alcohol
Identifiers
CAS Number	557-61-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28243 ;
ChemSpider	61689 ;
ECHA InfoCard	100.008.348
KEGG	C08387 ;
MeSH	1-octacosanol
PubChem CID	68406;
UNII	81I2215OVK ;
CompTox Dashboard (EPA)	DTXSID1025803 ;
	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 Key: CNNRPFQICPFDPO-UHFFFAOYSA-N ; 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;
	SMILES OCCCCCCCCCCCCCCCCCCCCCCCCCCCC;
Properties
Chemical formula	C28H58O
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).
	verify (what is ?)
	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] In mice, octacosanol reduces stress and restores stress-affected sleep back to normal.[6]

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References

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
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. 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. doi:10.1038/s41598-017-08874-2. PMC 5566941. PMID 28827687.

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[Baker-1] 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

[2] "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

[taylor-3] 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.

[4] Snider, SR (1984). "Octacosanol in parkinsonism". Annals of Neurology. 16 (6): 723. doi:10.1002/ana.410160615. PMID 6395790.

[5] 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.

[6] 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. doi:10.1038/s41598-017-08874-2. PMC 5566941. PMID 28827687.