63015-91-8

Basic information

• Product Name: Cholest-5-en-23-yn-3β-ol
• Synonyms: Cholest-5-en-23-yn-3β-ol
• CAS NO: 63015-91-8
• Molecular Formula: C27H42O
• Molecular Weight: 382.62178
• Mol File: 63015-91-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cholest-5-en-23-yn-3β-ol(CAS DataBase Reference)
• NIST Chemistry Reference: Cholest-5-en-23-yn-3β-ol(63015-91-8)
• EPA Substance Registry System: Cholest-5-en-23-yn-3β-ol(63015-91-8)

Safety Data

• Hazardous Substances Data: 63015-91-8(Hazardous Substances Data)

Upstream product

• 84582-62-7 (24S)-24H-Isocalysterol 
• 57331-04-1 (28R)-calysterol 
• 83511-84-6 (23R)-23,28-cyclostigmasta-5,24(28)-dien-3-β-ol 
• 85798-19-2 (23S)-23,28-cyclostigmasta-5,24(28)-dien-3-β-ol 

Relevant articles and documents

BIOSYNTHETIC STUDIES OF MARINE LIPIDS. 21. EXPERIMENTAL DEMONSTRATION OF A BIOSYNTHETIC INTERCONVERSION OF CYCLOPROPENE STEROLS IN THE SPONGE CALYX NICAEENSIS

In vivo isomerization of cyclopropenes has been demonstrated for the first time through feeding experiments of appropriately labeled cyclopropene sterols (1c-4c) in the sponge Calyx nicaeensis.

ACID-CATALYZED AND PHOTOCHEMICAL ISOMERIZATION OF STEROIDAL CYCLOPROPENES.

The acid-catalyzed and photochemical isomerization of two naturally occurring steroidal cyclopropenes, (28R)-calysterol and (23R)-23H-isocalysterol is described. Cyclopropene on treatment with methanolic sulfuric acid afforded 23-ethylated cholesterol derivatives containing conjugated diene systems or methoxylated side chains. The sole production of C-23 ethylated sterols demonstrates that this cyclopropene undergoes acid-promoted bond cleavage only between C-24 and C-28. By contrast, methanolic sulfuric acid treatment of the isomeric cyclopropene generated conjugated dienes with 24-methyl-24-homocholestane and 24-ethylcholestane side chains, together with their methoxylated derivatives. This implies that bond fission between C-23 and C-24, as well as C-23 and C-28, is operating in this instance, which is of mechanistic significance.