1-Octacosanol

{{short description|28-carbon primary fatty alcohol}}

{{Use dmy dates|date=July 2020}}

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477208352

| ImageFile=1-Octacosanol-folded.svg

| ImageSize=200px

| PIN=Octacosan-1-ol

| OtherNames=n-Octacosanol; Octacosyl alcohol; Octanosol; Montanyl alcohol; Cluytyl alcohol

|Section1={{Chembox Identifiers

| KEGG = C08387

| KEGG_Ref = {{keggcite|correct|kegg}}

| 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

| InChIKey = CNNRPFQICPFDPO-UHFFFAOYAC

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = CNNRPFQICPFDPO-UHFFFAOYSA-N

| CASNo=557-61-9

| CASNo_Ref = {{cascite|changed|??}}

| PubChem=68406

| SMILES = OCCCCCCCCCCCCCCCCCCCCCCCCCCCC

| ChemSpiderID = 61689

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| UNII = 81I2215OVK

| UNII_Ref = {{fdacite|correct|FDA}}

| ChEBI = 28243

| ChEBI_Ref = {{ebicite|correct|EBI}}

| MeSHName=1-octacosanol

}}

|Section2={{Chembox Properties

| C=28 | H=58 | O=1

| Appearance=

| Density=

| MeltingPtC=83

| BoilingPt=

| Solubility=

}}

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

}}

1-Octacosanol{{Pronunciation needed|date=December 2023}} (also known as n-octacosanol, octacosyl alcohol, cluytyl{{Pronunciation needed|date=December 2023}} alcohol, montanyl{{Pronunciation needed|date=December 2023}} 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.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 also occurs in wheat germ.{{cite web

|title=Octacosanol

|work=Natural Products (Professional)

|publisher=drugs.com

|url=https://www.drugs.com/npp/octacosanol.html

|quote=isolated from wheat germ oil or other plants

|accessdate=9 July 2009

|archiveurl=https://web.archive.org/web/20090603230755/http://www.drugs.com/npp/octacosanol.html

|archivedate=3 June 2009

|url-status=live

}}

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.{{cite journal | doi = 10.1016/S0899-9007(02)00869-9 | title = Octacosanol in human health | year = 2003 | last1 = Taylor | first1 = Johanna C | last2 = Rapport | first2 = Lisa | last3 = Lockwood | first3 = G.Brian | journal = Nutrition | volume = 19 | issue = 2 | pages = 192–5 | pmid = 12591561}} Octacosanol has been subject to preliminary study for its potential benefit for patients with Parkinson's disease.{{cite journal | pmid = 6395790 | year = 1984 | last1 = Snider | first1 = SR | title = Octacosanol in parkinsonism | volume = 16 | issue = 6 | pages = 723 | doi = 10.1002/ana.410160615 | journal = Annals of Neurology| s2cid = 43313071 }}{{cite journal | pmid = 20581854 | year = 2010 | last1 = Wang | first1 = T | last2 = Liu | first2 = YY | last3 = Wang | first3 = X | last4 = Yang | first4 = N | last5 = Zhu | first5 = HB | last6 = Zuo | first6 = PP | title = Protective effects of octacosanol on 6-hydroxydopamine-induced Parkinsonism in rats via regulation of ProNGF and NGF signaling | volume = 31 | issue = 7 | pages = 765–74 | doi = 10.1038/aps.2010.69 | journal = Acta Pharmacologica Sinica| pmc = 4007727 }} Studies have also found that octacosanol may inhibit the production of cholesterol. In mice, octacosanol reduces stress and restores stress-affected sleep back to normal.{{cite journal|last1 = Kaushik | first1 = MK | last2 = Aritake | first2 = K | last3 = Takeuchi | first3 = A | last4 = Yanagisawa | first4 = M | last5 = Urade | first5 = Y|title=Octacosanol restores stress-affected sleep in mice by alleviating stress|journal=Scientific Reports|date=21 August 2017|volume=7| issue = 1 | pages = 8892 |doi=10.1038/s41598-017-08874-2| pmid = 28827687 | pmc = 5566941 | bibcode = 2017NatSR...7.8892K }}

References

{{reflist}}

{{Alcohols}}

{{DEFAULTSORT:Octacosanol, 1-}}

Category:Fatty alcohols

Category:Primary alcohols

Category:Alkanols