dihydrocholesterol

zymostanol

CAS: 80-97-7 C27 H48 O MW: 388.67876000

Identification

Namedihydrocholesterol
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 Number80-97-7
EINECS201-315-8
FDA UNII8M308U816E
Molecular FormulaC27 H48 O
Molecular Weight388.67876000
MDL NumberMFCD00066413
Beilstein2418594

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

CosIngcosmetic data
Cosmetic Usesskin conditioning

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryemollients, skin conditioning
Recommendation for dihydrocholesterol usage levels up tonot for fragrance use.
Recommendation for dihydrocholesterol flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

coffee bean oat leaf oat seed walnut english walnut nut

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.