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Details

Stereochemistry ACHIRAL
Molecular Formula C28H58O
Molecular Weight 410.7606
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 1-OCTACOSANOL

SMILES

CCCCCCCCCCCCCCCCCCCCCCCCCCCCO

InChI

InChIKey=CNNRPFQICPFDPO-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C28H58O
Molecular Weight 410.7606
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: description was created based on several sources, including https://www.drugs.com/npp/octacosanol.html https://www.ncbi.nlm.nih.gov/pubmed/12591561 https://www.ncbi.nlm.nih.gov/pubmed/20301014

Octacosanol, a low–molecular-weight primary aliphatic alcohol, is the main component of a natural product wax extracted from plants. Most studies have used a wheat-germ oil extract, or policosanol, a natural mixture of primary alcohols isolated from sugar cane wax, of which octacosanol is the main component (approximately 67% of policosanol is octacosanol). It has a number of indications for its use, many of which are currently being researched. Moreover, a small controlled study showed that some patients with mild Parkinsonism claimed of benefit from octacosanol. Although some research has been conducted using policosanol, little research is currently available that focuses on octacosanol alone. Studies have also found that octacosanol may inhibit the production of cholesterol. In the early 1990s, researchers at Dalmer Laboratories in La Habana Cuba isolated and produced the first policosanol (PC) supplement. The original PC supplement has been approved as a cholesterol-lowering drug in over 25 countries throughout the Caribbean and South America. Cuban studies claim that 1 to 20 mg/day of the original PC supplement are effective at producing significant reductions in total cholesterol (TC) and low-density lipoprotein cholesterol (LDL-C). These studies also show that PC supplements are potent antioxidants, promote proper arterial endothelial cell function, inhibit platelet aggregation and thrombosis, and serve as effective treatments for intermittent claudication. However, for the most part, those studies reporting therapeutic efficacy of PC were carried out by one research group situated in Cuba. Conversely, research groups outside of Cuba have failed to validate the cholesterol-lowering and antioxidant efficacy of PC. Cuban researchers, however, continue to claim that the efficacy is attributed to the unique purity and composition of the original PC preparation, a mixture not found in PC products used by external research groups. The absence of independent and external studies confirming the therapeutic benefits of PC in disease prevention and treatment raises questions regarding their true efficacy. Octacosanol also may prevent from atherosclerosis through activation of the PI3K/Akt and MAPK/Erk1/2 signaling pathways.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Trace determination of 1-octacosanol in rat plasma by solid-phase extraction with Tenax GC and capillary gas chromatography.
2001 Oct 5
Remediation of fine fractions of dredged sediments by flotation.
2002 Aug
Inhibition of rat lipoprotein lipid peroxidation by the oral administration of D003, a mixture of very long-chain saturated fatty acids.
2002 Jan
Study of the interaction between policosanol and excipients.
2002 Mar-Apr
[A new chromone glycoside from Cassia siamea lam].
2003 Feb
Octacosanol in human health.
2003 Feb
[Studies on chemical constituents of Choerospondias axillaris].
2003 Jan
Wheat germ policosanol failed to lower plasma cholesterol in subjects with normal to mildly elevated cholesterol concentrations.
2004 Oct
Quantitative determination of sterols and other alcohols in overland flow from grazing land and possible source materials.
2005 Aug
Policosanol has no antioxidant activity in human low-density lipoprotein but increases excretion of bile acids in hamsters.
2005 Aug 10
Antihyperlipidaemic effect of a Monascus purpureus brand dietary supplement on a large sample of subjects at low risk for cardiovascular disease: a pilot study.
2005 Dec
Policosanol contents and compositions of wheat varieties.
2005 Jul 13
Antibacterial potential from Indian Suregada angustifolia.
2005 Jul 14
In vitro and in vivo study of octacosanol metabolism.
2005 Mar-Apr
What do microbes encounter at the plant surface? Chemical composition of pea leaf cuticular waxes.
2005 Sep
Secondary metabolites from Senecio burtonii (Compositae).
2006 Apr
Structural analysis of wheat wax (Triticum aestivum, c.v. 'Naturastar' L.): from the molecular level to three dimensional crystals.
2006 Jan
Policosanol content and composition in perilla seeds.
2006 Jul 26
Policosanol inhibits cholesterol synthesis in hepatoma cells by activation of AMP-kinase.
2006 Sep
Comparison of composition and absorption of sugarcane policosanols.
2007 Feb
[Study on the active components of Nardostachys chinensis].
2007 Jan
Quantification of sterols and aliphatic alcohols in Mediterranean stone pine (Pinus pinea L.) populations.
2007 Mar 21
In silico toxicological screening of natural products.
2008
Effects of emulsified policosanols with different chain lengths on cholesterol metabolism in heterozygous LDL receptor-deficient mice.
2008 Apr
Changes in cholesterol kinetics following sugar cane policosanol supplementation: a randomized control trial.
2008 Apr 30
Octacosanol administration to humans decreases neutral sterol and bile acid concentration in feces.
2008 Feb
Octacosanol attenuates disrupted hepatic reactive oxygen species metabolism associated with acute liver injury progression in rats intoxicated with carbon tetrachloride.
2008 Mar
Three novel compounds from the leaves of Smallanthus sonchifolius.
2008 Nov-Dec
Application of GC-MS for the detection of lipophilic compounds in diverse plant tissues.
2009 Apr 24
Trace quantification of 1-octacosanol and 1-triacontanol and their main metabolites in plasma by liquid-liquid extraction coupled with gas chromatography-mass spectrometry.
2009 Dec 15
Antiatherosclerotic function of Kokuto, Okinawan noncentrifugal cane sugar.
2009 Jan 14
Solid lipid nanoparticles: a modern formulation approach in drug delivery system.
2009 Jul
Long-chain fatty alcohols from pomace olive oil modulate the release of proinflammatory mediators.
2009 Mar
Policosanol, alpha-tocopherol, and moisture content as a function of timing of harvest of Switchgrass (Panicum virgatum L.).
2009 May 13
Regulation of HMGCoA reductase activity by policosanol and octacosadienol, a new synthetic analogue of octacosanol.
2009 Oct
Effects of Phyllanthus reticulatus on lipid profile and oxidative stress in hypercholesterolemic albino rats.
2010 Dec
Traditional herbal medicine in far-west Nepal: a pharmacological appraisal.
2010 Dec 13
Nutritional bioactive components of wheat straw as affected by genotype and environment.
2010 Jan
Phytopharmacology of Ficus religiosa.
2010 Jul
Protective effects of octacosanol on 6-hydroxydopamine-induced Parkinsonism in rats via regulation of ProNGF and NGF signaling.
2010 Jul
Plant neighbor identity influences plant biochemistry and physiology related to defense.
2010 Jun 17
Synthesis of 1-octacosanol and GC-C-IRMS discrimination of samples from different origin.
2010 Mar
Metabolic profiling of Arabidopsis thaliana epidermal cells.
2010 Mar
Phytoconstituents from Alpinia purpurata and their in vitro inhibitory activity against Mycobacterium tuberculosis.
2010 Oct
Patents

Sample Use Guides

10 mg/day
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Jun 26 14:52:48 UTC 2021
Edited
by admin
on Sat Jun 26 14:52:48 UTC 2021
Record UNII
81I2215OVK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
1-OCTACOSANOL
Systematic Name English
OCTACOSANOL [WHO-DD]
Common Name English
OCTACOSANOL [MI]
Common Name English
OCTANOSOL
Common Name English
OCTACOSANOL
MART.   MI   WHO-DD  
Systematic Name English
CLUYTYL ALCOHOL
Common Name English
OCTACOSANOL (CONSTITUENT OF SAW PALMETTO) [DSC]
Common Name English
NSC-10770
Code English
OCTACOSYL ALCOHOL
Systematic Name English
MONTANYL ALCOHOL
Systematic Name English
N-OCTACOSANOL
Common Name English
OCTACOSANOL [MART.]
Common Name English
Classification Tree Code System Code
DSLD 545 (Number of products:149)
Created by admin on Sat Jun 26 14:52:48 UTC 2021 , Edited by admin on Sat Jun 26 14:52:48 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
209-181-2
Created by admin on Sat Jun 26 14:52:48 UTC 2021 , Edited by admin on Sat Jun 26 14:52:48 UTC 2021
PRIMARY
CAS
557-61-9
Created by admin on Sat Jun 26 14:52:48 UTC 2021 , Edited by admin on Sat Jun 26 14:52:48 UTC 2021
PRIMARY
EPA CompTox
557-61-9
Created by admin on Sat Jun 26 14:52:48 UTC 2021 , Edited by admin on Sat Jun 26 14:52:48 UTC 2021
PRIMARY
DRUG BANK
DB11220
Created by admin on Sat Jun 26 14:52:48 UTC 2021 , Edited by admin on Sat Jun 26 14:52:48 UTC 2021
PRIMARY
FDA UNII
81I2215OVK
Created by admin on Sat Jun 26 14:52:48 UTC 2021 , Edited by admin on Sat Jun 26 14:52:48 UTC 2021
PRIMARY
RXCUI
12166
Created by admin on Sat Jun 26 14:52:48 UTC 2021 , Edited by admin on Sat Jun 26 14:52:48 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C1505
Created by admin on Sat Jun 26 14:52:48 UTC 2021 , Edited by admin on Sat Jun 26 14:52:48 UTC 2021
CONCEPT Dietary Supplement
NCI_THESAURUS
C87340
Created by admin on Sat Jun 26 14:52:48 UTC 2021 , Edited by admin on Sat Jun 26 14:52:48 UTC 2021
PRIMARY
MERCK INDEX
M8103
Created by admin on Sat Jun 26 14:52:48 UTC 2021 , Edited by admin on Sat Jun 26 14:52:48 UTC 2021
PRIMARY Merck Index
MESH
C044309
Created by admin on Sat Jun 26 14:52:48 UTC 2021 , Edited by admin on Sat Jun 26 14:52:48 UTC 2021
PRIMARY
WIKIPEDIA
1-OCTACOSANOL
Created by admin on Sat Jun 26 14:52:48 UTC 2021 , Edited by admin on Sat Jun 26 14:52:48 UTC 2021
PRIMARY
PUBCHEM
68406
Created by admin on Sat Jun 26 14:52:48 UTC 2021 , Edited by admin on Sat Jun 26 14:52:48 UTC 2021
PRIMARY
EVMPD
SUB34737
Created by admin on Sat Jun 26 14:52:48 UTC 2021 , Edited by admin on Sat Jun 26 14:52:48 UTC 2021
PRIMARY
DRUG CENTRAL
4668
Created by admin on Sat Jun 26 14:52:48 UTC 2021 , Edited by admin on Sat Jun 26 14:52:48 UTC 2021
PRIMARY
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