474-63-5

Basic information

• Product Name: 5,24(28)-Cholestadien-24-methylen-3beta-ol
• Synonyms: Cholesterol, 24-methylene-;Ergosta-5,24(28)-dien-3beta-ol;Ergosta-5,24(28)-dien-3beta-ol (8ci);Ergosta-5,24(28)-dien-3-ol, (3beta)- (9ci);Nsc 232664;24-Methylcholesta-5,24(28)-dien-3β-ol;5α-Ergosta-5,24(28)-dien-3β-ol;Chalinasterol
• CAS NO: 474-63-5
• Molecular Formula: C₂₈H₄₆O
• Molecular Weight: 398.67
• Mol File: 474-63-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 490.3°Cat760mmHg
• Flash Point: 213.8°C
• Appearance: /
• Density: 0.98g/cm³
• Vapor Pressure: 1.14E-11mmHg at 25°C
• Refractive Index: 1.528
• CAS DataBase Reference: 5,24(28)-Cholestadien-24-methylen-3beta-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 5,24(28)-Cholestadien-24-methylen-3beta-ol(474-63-5)
• EPA Substance Registry System: 5,24(28)-Cholestadien-24-methylen-3beta-ol(474-63-5)

Safety Data

• Hazardous Substances Data: 474-63-5(Hazardous Substances Data)

Usage

Uses

Ostreasterol is a marine steroid, and also a derivative compound of hydroxycholesterol (H918040), which functions as the main cholesterol elimination product of the brain and was found to be increased in serum of Alzheimer patients.

Definition

ChEBI: A 3beta-sterol having the structure of cholesterol with a methylene group at C-24.

InChI:InChI=1/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9,18,20,22-26,29H,3,7-8,10-17H2,1-2,4-6H3/t20-,22+,23+,24-,25+,26+,27+,28-/m1/s1

Upstream product

• 68844-31-5 (1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-6-((R)-1,5-Dimethyl-4-methylene-hexyl)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalene 
• 51231-25-5 3α,5-cyclo-22-iodo-5α-23,24-bisnorcholan-6β-ol 6-methyl ether 
• 105395-33-3 (1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-Methoxy-3a,5a-dimethyl-6-[(E)-(R)-1-methyl-4-phenylselanyl-5-(toluene-4-sulfonyl)-pent-4-enyl]-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalene 
• 105395-37-7 (1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-6-{(R)-1,5-Dimethyl-4-[1-(toluene-4-sulfonyl)-meth-(E)-ylidene]-hexyl}-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalene 
• 105395-38-8 [(R)-5-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-Methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-hex-1-ynyl]-trimethyl-silane 
• 105395-32-2 (1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-Methoxy-3a,5a-dimethyl-6-((R)-1-methyl-pent-4-ynyl)-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalene 
• 497841-91-5 5α,6β-dibromostigmast-22-en-3β-(2-tetrahydropyranyl)ether 
• 287471-28-7 stigmast-4,22-dien-3β-(2-tetrahydropyranyl)ether 
• 89495-47-6 (22-trans)-hydroxy-3β-cholestadiene-5,22-one-24 
• 121077-68-7 (3-methyl-2-oxobutyl)triphenyl-arsonium bromide 
• 53906-49-3 3β-ol-23,24-bisnor-chol-5-en-22-al hemihydrochloride 
• 83-48-7 Stigmasterol 
• 20981-59-3 3β-acetoxy-cholest-5-en-24-one 
• 17752-16-8 24-oxocholesterol 

Downstream Products

• 55688-44-3 24-methylene-cholest-4-ene-3-one 
• 481-14-1 28-Isofucosterol 
• 481-14-1 isofucosterol 
• 2364-23-0 clerosterol 
• 6538-02-9 ergostanol 
• 474-60-2 campestanol 
• 1900-53-4 campesteryl acetate 
• 474-62-4 Campesterol 
• 50-00-0 formaldehyd 
• 57-88-5 cholesterol 
• 313-04-2 demosterol 
• 20780-41-0 Δ^5,24(28)-ergostadien-3β-ol 
• 82949-88-0 ergosta-5,23(Z)-dien-3β-ol 
• 79733-00-9 24-methylcholesta-5,E-23-dien-3β-ol 

Relevant articles and documents

Synthesis of polyhydroxysterols (V): Efficient and stereospecific synthesis of 24-methylene-cholest-5-ene-3β,7α-diol and its C-7 epimer

This paper describes the efficient and stereospecific synthesis of cytotoxic dihydroxylated sterols, 24-methylene-cholest-5-ene-3β,7α- diol 1, and its C-7 epimer, 24-methylene-cholest-5-ene-3β,7β-diol 2. The crux of the synthesis is that the selective allylic oxidation of 24-methylene-cholesteryl acetate proceeds to 24-methylene-7-keto-cholesteryl acetate without extensive byproduct formation from reaction at the Δ24(28) double bond. This methodology may be useful for the preparation of other oxysterols with non-standard side chains.

Synthesis of polyhydroxysterols (III): synthesis and structural elucidation of 24-methylenecholest-4-en-3beta,6 alpha-diol.

Using stigmasterol as the starting material, 24-methylenecholest-4-en-3beta,6 alpha-diol (2) was synthesized in eight steps in 13% overall yield. The introduction of the sterol side-chain was carried out using (3-methyl-2-oxobutyl)-triphenylarsonium bromide (11) and K(2)CO(3) in a solid-liquid phase-transfer Wittig reaction. Construction of the steroidal nucleus was finished by oxidation of 24-methylenecholest-5-en-3beta-ol (9) with pyridinium chlorochromate (PCC) in dichloromethane at ambient temperature and by reduction of 24-methylenecholest-4-en-3,6-dione (10) with NaBH(4) in the presence of CeCl(3).7H(2)O.

APPLICATION OF SELENOSULFONATION TO MARINE STEROL SYNTHESIS. PREPARATION OF 24,28-DEHYDROAPLYSTEROL, XESTOSTEROL AND OSTREASTEROL FROM A COMMON ACETYLENIC INTERMADIATE

The title compounds were synthesized from a readily available steroidal acetylene by a protocol employing selenosulfonation, introduction of the appropriate side chain at C-24 via an alkyl selenocuprate, and reductive desulfonylation.