dihydrocholesterol
zymostanol
Identification
| Name | dihydrocholesterol |
| IUPAC | (3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol |
| CAS Number | 80-97-7 |
| EINECS | 201-315-8 |
| FDA UNII | 8M308U816E |
| Molecular Formula | C27 H48 O |
| Molecular Weight | 388.67876000 |
| MDL Number | MFCD00066413 |
| Beilstein | 2418594 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 141.50 °C. @ 760.00 mm Hg |
| Boiling Point | 455.53 °C. @ 760.00 mm Hg (est) |
| Flash Point | 375.00 °F. TCC ( 190.70 °C. ) (est) |
| logP (o/w) | 10.065 (est) |
| Soluble in | water, 0.0003391 mg/L @ 25 °C (est) |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | skin conditioning |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | emollients, skin conditioning |
| Recommendation for dihydrocholesterol usage levels up to | not for fragrance use. |
| Recommendation for dihydrocholesterol flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
5-alpha-
cholestan-3-beta-ol
(3b,5a)-
cholestan-3-ol
5a-
cholestan-3b-ol
cholestanol
5b-
cholestanol
b-
cholestanol
(+)-
dihydrocholesterol
5a-
dihydrocholesterol
(3S,5S,8R,9S,10S,13R,14S,17R)-10,13-
dimethyl-17-[(2R)-6-methyl-2-heptanyl]hexadecahydro-1H-cyclopenta[a]phenanthren-3-ol
(3S,5S,8R,9S,10S,13R,14S,17R)-10,13-
dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
zymostanol
PubMed:
Synthesis, spectroscopic and semiempirical studies of new quaternary alkylammonium conjugates of sterols.
PubMed:
Sterol composition of shellfish species commonly consumed in the United States.
PubMed:
Ordered-disordered domain coexistence in ternary lipid monolayers activates sphingomyelinase by clearing ceramide from the active phase.
PubMed:
Structural requirements of virion-associated cholesterol for infectivity, buoyant density and apolipoprotein association of hepatitis C virus.
PubMed:
The origin of cholesterol's condensing effect.
PubMed:
Influence of the nature of the sterol on the behavior of palmitic acid/sterol mixtures and their derived liposomes.
PubMed:
Micron-scale phase segregation in lipid monolayers induced by myelin basic protein in the presence of a cholesterol analog.
PubMed:
Fluconazole modulates membrane rigidity, heterogeneity, and water penetration into the plasma membrane in Saccharomyces cerevisiae.
PubMed:
Ordered nanoclusters in lipid-cholesterol membranes.
PubMed:
Critical exponents for line tension and dipole density difference from lipid monolayer domain boundary fluctuations.
PubMed:
Steroid 5alpha-reductase activity of Treponema denticola.
PubMed:
Comparison of the interaction of dihydrocholesterol and cholesterol with sphingolipid or phospholipid Langmuir monolayers.
PubMed:
Structural requirements of cholesterol for binding to Vibrio cholerae hemolysin.
PubMed:
Insertion selectivity of antimicrobial peptide protegrin-1 into lipid monolayers: effect of head group electrostatics and tail group packing.
PubMed:
Thermodynamic equilibrium of domains in a two-component Langmuir monolayer.
PubMed:
Method validation for the simultaneous determination of fecal sterols in surface waters by gas chromatography-mass spectrometry.
PubMed:
[The photobiology of vitamin D--a topic of renewed focus].
PubMed:
Phase behavior of lipid monolayers containing DPPC and cholesterol analogs.
PubMed:
An efficient diethyl ether-based soxhlet protocol to quantify faecal sterols from catchment waters.
PubMed:
Purification and some properties of cholesterol oxidase stable in detergents from gamma-proteobacterium Y-134.
PubMed:
Impact of membrane cholesterol content on the resistance of vesicles to surfactant attack.
PubMed:
Kinetics for the collapse of trilayer liquid-crystalline disks from a monolayer at an air-water interface.
PubMed:
Sterol structure determines miscibility versus melting transitions in lipid vesicles.
PubMed:
Sterol stringency of proliferation and cell cycle progression in human cells.
PubMed:
Calcium oxalate monohydrate precipitation at membrane lipid rafts.
PubMed:
Impact of 10 dietary sterols on growth and reproduction of Daphnia galeata.
PubMed:
Contrast inversion in the epifluorescence of cholesterol-phospholipid monolayers.
PubMed:
Unraveling the mystery surrounding cholesterol's condensing effect.
PubMed:
Liquid-crystalline collapse of pulmonary surfactant monolayers.
PubMed:
Critical points in charged membranes containing cholesterol.
PubMed:
Two fatty acids can replace one phospholipid in condensed complexes with cholesterol.
PubMed:
Sterol-induced upregulation of phosphatidylcholine synthesis in cultured fibroblasts is affected by the double-bond position in the sterol tetracyclic ring structure.
PubMed:
Miscibility critical pressures in monolayers of ternary lipid mixtures.
PubMed:
Chemical activity of cholesterol in membranes.
PubMed:
Electric field effect on cholesterol-phospholipid complexes.
PubMed:
The effect of sterol structure on membrane lipid domains reveals how cholesterol can induce lipid domain formation.
PubMed:
Condensed complexes of cholesterol and phospholipids.
PubMed:
[Congenital malformations of the genitourinary tract in children with Smith-Lemli-Opitz syndrome].
PubMed:
New method for determination of fecal sterols in urine using non-chlorinated solvents.
PubMed:
Liquid-liquid immiscibility in lipid monolayers.
PubMed:
Acid-catalyzed plasmenylcholine hydrolysis and its effect on bilayer permeability: a quantitative study.
PubMed:
Critical pressures in multicomponent lipid monolayers.
PubMed:
Inverse relationship between plasma cholestanol concentrations and bile acid synthesis in sitosterolemia.
PubMed:
Electric field-induced concentration gradients in lipid monolayers.
PubMed:
Gallstone formation in cholestanol-fed mice.
PubMed:
Effect of sterol structure on the partition of sterol between phospholipid vesicles of different composition.
PubMed:
Influence of sterol structure on phospholipid phase behavior as detected by parinaric acid fluorescence spectroscopy.
PubMed:
LM cell growth and membrane lipid adaptation to sterol structure.
PubMed:
Hypersecretion of mucus glycoprotein by the gallbladder epithelium in experimental cholelithiasis.
PubMed:
Dihydrocholesterol-induced gallstones in the rabbit: evidence that bile acids cause gallbladder epithelial injury.
PubMed:
Quantitative GLC analysis of sterols in biological samples.
PubMed:
Epithelial cell proliferation in diverse models of experimental cholelithiasis.
PubMed:
Enhanced fluid transport across gallbladder mucosa in experimental cholelithiasis.
PubMed:
Effect of exogenous lipid on lipid synthesis by bone and bone cell cultures.
PubMed:
[Dihydrocholesterol-induced gallstone in rabbits].
PubMed:
The interaction of nitrogen dioxide with monomolecular films of cholesterol, dihydrocholesterol, and cholesteryl acetate.
PubMed:
Biliary mucous substances in dihydrocholesterol-induced cholelithiasis.
PubMed:
[Electron spin resonance of free radicals in x-irradiated cholesterol and 5,6-dihydrocholesterol].
PubMed:
The occurrence of 5alpha-cholestan-3beta-ol (Dihydrocholesterol) in human skin surface lipid.
PubMed:
Suppression of cholesterol synthesis in rat liver by dihydrocholesterol administration.
PubMed:
ON GALLSTONE FORMATION IN RABBITS INDUCED BY DIHYDROCHOLESTEROL. 2. INFLUENCE OF OLIVE OIL IN THE DIET.
PubMed:
[SEPARATION OF CHOLESTEROL, DESMOSTEROL AND 5-DIHYDROCHOLESTEROL BY THIN-LAYER CHROMATOGRAPHY AFTER PROPIONYLATION].
PubMed:
BIOSYNTHESIS OF 5-ALPHA-CHOLESTAN-3-BETA-OL IN THE RABBIT AND GUINEA PIG.
PubMed:
[RESEARCH ON BILIARY CALCULOSIS INDUCED BY CHOLESTANOL IN RABBITS].
PubMed:
SEPARATION OF NUCLEAR SATURATED FROM UNSATURATED STEROLS.
PubMed:
ON GALLSTONE FORMATION IN RABBITS INDUCED BY DIHYDROCHOLESTEROL.
PubMed:
METABOLISM OF COPROSTANOL-C14 AND CHOLESTANOL-4-C14 IN MAN.
PubMed:
DIFFERENTIAL MIGRATION OF STEROL ACETATES ON SILICA GELS AND ITS APPLICATION TO THE FRACTIONATION OF STEROL MIXTURES. ANL-6723.
PubMed:
Biological studies of dihydro-cholesterol. V. Effect of androgens upon the biologic disposition of dihydrocholesterol in the rabbit.
PubMed:
A new method for the determination of dihydrocholesterol in tissues.
PubMed:
PAPER CHROMATOGRAPHY OF SOME CHOLESTEROL DERIVATIVES.
PubMed:
Influence of added cholesterol and dihydrocholesterol upon the multiplication of entamoeba histolytica in MS-F medium.
PubMed:
Early pathologic and biochemical changes in rabbits fed dihydrocholesterol.
PubMed:
Experimental aortic atherosclerosis in rabbits following the ingestion of dihydrocholesterol.
PubMed:
Comparison of lymphatic absorption of dihydrocholesterol and cholesterol in the rat.
PubMed:
Biological studies of dihydrocholesterol. IV. Effect of bile acids and other choleretic agents on dihydrocholesterol-induced cholelithiasis in the rabbit.
PubMed:
Biological studies of dihydrocholesterol. III. Regression of dihydrocholesterol-induced cholecystitis and cholelithiasis in the rabbit.
PubMed:
Biological studies of dihydrocholesterol. II. Effect of dehydrocholic acid on dihydrocholesterol-induced cholelithiasis in the rabbit.
PubMed:
Effect of dihydrocholesterol and beta-sitosterol on cholesterol atherosclerosis in rabbits.
PubMed:
Biological studies of dihydrocholesterol; production of biliary concrements and inflammatory lesions of the biliary tract in rabbits.
PubMed:
Effect of dihydrocholesterol and soybean sterols on cholesterol metabolism in rabbit and rat.
PubMed:
Absorption of dihydrocholesterol and soya sterols by the rat's intestine.
PubMed:
Production of arteriosclerosis in birds by the prolonged feeding of dihydrocholesterol.
PubMed:
Effect of dihydrocholesterol and soy bean sterols on elevated tissue cholesterol.
PubMed:
Prevention of the cholesterol type of fatty livers in mice by dietary dihydrocholesterol.
PubMed:
The effect of dihydrocholesterol on the absorption of cholesterol by the rat.
PubMed:
Effect of dihydrocholesterol (cholestanol) administration on plasma cholesterol and atherosclerosis in the rabbit.
PubMed:
Prevention of plasma cholesterol elevation and atheromatosis in the cholesterol-fed bird by the administration of dihydrocholesterol.
PubMed:
The formation of coprosterol in the intestine: Possible rôle of dihydrocholesterol, and a method of determining dihydrocholesterol in presence of cholesterol.