2034-72-2

Basic information

• Product Name: Stigmasta-3,5-dien-7-one
• Synonyms: Stigmasta-3,5-dien-7-one;Tremulone;β-Saccharostenone
• CAS NO: 2034-72-2
• Molecular Formula: C₂₉H₄₆O
• Molecular Weight: 410.67
• Mol File: 2034-72-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Stigmasta-3,5-dien-7-one(CAS DataBase Reference)
• NIST Chemistry Reference: Stigmasta-3,5-dien-7-one(2034-72-2)
• EPA Substance Registry System: Stigmasta-3,5-dien-7-one(2034-72-2)

Safety Data

• Hazardous Substances Data: 2034-72-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C29H46O/c1-7-21(19(2)3)12-11-20(4)23-13-14-24-27-25(15-17-29(23,24)6)28(5)16-9-8-10-22(28)18-26(27)30/h8,10,18-21,23-25,27H,7,9,11-17H2,1-6H3/t20-,21-,23-,24+,25+,27+,28+,29-/m1/s1

Upstream product

• 18376-53-9 (24R)-3β-acetoxystigmast-5-en-7-one 
• 104-15-4 toluene-4-sulfonic acid 
• 108-88-3 toluene 
• 95826-57-6 7-oxostigmast-5-en-3-β-yl chloride 
• 145985-28-0 7-oxo-poriferast-5-en-3β-yl-acetate 
• 145163-97-9 7-Oxositosterol 
• 915-05-9 clionasteryl acetate 
• 145985-29-1 stigmast-3β,7α-dihydroxyl-5-ene 
• 83-46-5 clionasterol 
• 33999-15-4 (24R)-3β-chlorostigmast-5-ene 

Relevant articles and documents

P -TsOH-Catalyzed one-pot transformation of di- and trihydroxy steroids towards diverse A/B-ring oxo-functionalization

A solid support-mediated p-TsOH-catalyzed milder transformative protocol was developed to furnish diverse ring-A and/or ring-B oxo-functionalized steroids. To furnish interesting isomers involving the A/B-ring of biomolecules in a one-pot approach, only solid supports (and not solution!) were found to be effective. p-TsOH/SiO2-oxidation of 4β-hydroxycholesterol, the major oxysterol in human circulation, into a mixture of cholest-4-en-3-one, cholest-4-ene-3,6-dione, and 5α-cholestane-3,6-dione was the starting point for the investigations herein. The reaction protocol was optimized in detail, and efforts were carried out toward gaining an understanding of the mechanistic aspects favoring the solid support, and a possible synergetic catalytic system involving p-TsOH and SiO2 was expected to be a key part. Application of the novel methodology to 4β,7α-dihydroxy steroids resulted in the desired diverse ketosteroids through oxidation/oxidative dehydration, which generalized the process as a facile multi-oxo-functionalization steroidal transformation.

MINOR C29-STEROIDS FROM THE MARINE RED ALGA, GRACILARIA EDULIS

Four minor C29-steroids, poriferast-5-en-3β-ol (clionasterol), 3β-hydroxyporiferast-5-en-7-one, poriferast-5-en-3β,7α-diol and poriferasta-3,5-diene-7-one were isolated from the marine red alga, Gracilaria edulis.This is the first report of the characterization of the last three compounds from the natural source and the first compound from a species of Gracilaria. Key Word Index - Gracilaria edulis; Gracilariaceae; marine red alga; steroids; 3β-hydroxyporiferast-5-en-7-one; poriferast-5-en-3β,7α-diol; poriferasta-3,5-dien-7-one.

Baeyer-Villiger Oxidation of Some α,β-Unsaturated Ketones in Stigmastane Series

The perbenzoic acid oxidation of 7-oxostigmast-5-en-3β-yl chloride (I) gives 7-oxostigmast-3,5-diene (III), the formyl lactone (V) and the secoacid (VI). 7-Oxostigmast-5-en-3β-yl acetate (II) provides the formyl lactone (VII) and compound (VI). 7-Oxostigmast-3,5-diene (III) under similar conditions gives the epoxide (VIII), the diol (IX), the ε-lactone (X) and the dihydroxy epoxide (XI). 7-Oxostigmast-5-ene (IV) gives only the secoacid (XII).The products have been characterized on the basis of their chemical and spectral properties.