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1-Octacosanol

From Wikipedia, the free encyclopedia
28-carbon primary fatty alcohol

1-Octacosanol
Names
Preferred IUPAC name
Octacosan-1-ol
Other names
n-Octacosanol; Octacosyl alcohol; Octanosol; Montanyl alcohol; Cluytyl alcohol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard100.008.348Edit this at Wikidata
KEGG
MeSH1-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 checkY
    Key: CNNRPFQICPFDPO-UHFFFAOYSA-N checkY
  • 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
C28H58O
Molar mass410.771 g·mol−1
Melting point83 °C (181 °F; 356 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

1-Octacosanol[pronunciation?] (also known asn-octacosanol, octacosyl alcohol, cluytyl[pronunciation?] alcohol, montanyl[pronunciation?] alcohol) is a straight-chainaliphatic 28-carbonprimaryfatty alcohol that is common in theepicuticular waxes of plants, including the leaves of many species ofEucalyptus, of mostforage andcerealgrasses, ofAcacia,Trifolium,Pisum and many otherlegume genera among many others, sometimes as the major wax constituent.[1] Octacosanol also occurs in wheat germ.[2]

Chemistry

[edit]

Octacosanol is insoluble in water but freely soluble in low molecular-weightalkanes and inchloroform.

Biological effects

[edit]

Octacosanol is the main component in the mixturepolicosanol.[3] Octacosanol has been subject to preliminary study for its potential benefit for patients withParkinson's disease.[4][5] Studies have also found that octacosanol may inhibit the production ofcholesterol.[3] In mice, octacosanol reduces stress and restores stress-affected sleep back to normal.[6]

References

[edit]
  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. Retrieved9 July 2009.isolated from wheat germ oil or other plants
  3. ^abTaylor, 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.S2CID 43313071.
  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.Bibcode:2017NatSR...7.8892K.doi:10.1038/s41598-017-08874-2.PMC 5566941.PMID 28827687.
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