23656-66-8

Usage

Compound

22-dehydrodesmosterol

Found in

plants and algae

Precursor to

cholesterol in animals

Role

biosynthesis of steroids

Key intermediate in

synthesis of various sterol compounds

Inhibitor of

HMG-CoA reductase enzyme

Potential properties

antioxidant, anti-inflammatory

Studied for

cardiovascular and metabolic diseases, treatment of cancer and other diseases

InChI:InChI=1/C27H42O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h6-9,19,21-25,28H,10-17H2,1-5H3/b8-6+/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

Upstream product

• 80907-92-2 (22E,25R,S)-26-(dimethylamino)cholesta-5,22-dien-3β-ol 
• 80907-91-1 (20S,22R,S)-3β-acetoxychola-5,23-dien-22-ol 
• 25819-77-6 (S)-2-((1aR,3aR,3bS,5aS,6R,8aS,8bS)-10-Methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-propionaldehyde 
• 80925-45-7 (22E,25R,S)-N,N-dimethyl-3β-acetoxycholesta-5,22-dien-26-amide 
• 80907-93-3 (22E,25R,S)-26-(dimethylamino)cholesta-5,22-dien-3β-ol N-oxide 
• 34714-34-6 cholesta-5,22(E),25-trien-3β-ol 
• 60015-88-5 (1aR,3aR,3bS,5aR,6R,8aS,8bS)-6-((E)-(R)-1,5-Dimethyl-hexa-2,4-dienyl)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalene 
• 25819-82-3 22E-cholesta-5,22,24-trien-3β-yl acetate 
• 89472-03-7 (E)-(R)-4-((1aR,3aR,3bS,5aR,6R,8aS,8bS)-10-Methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-pent-2-enoic acid ethyl ester 
• 56259-13-3 (E)-(R)-4-((1aR,3aR,3bS,5aR,6R,8aS,8bS)-10-Methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-pent-2-en-1-ol 

Relevant academic research and scientific papers

MECHANISM OF STIGMASTEROL DEALKYLATION IN INSECT

Deuterated stigmasterols (10, 11 and 12) were chemically synthesized and fed to silkworm larvae.GC-MS analysis of the metabolites, cholesterol (4) and desmosterol (6), indicates the migration of 25-hydrogen to C-24position during stigmasterol dealkylation. 22,24(28)-Dienes (8a and 8b) were shown to be converted to 22,24-diene (5), desmosterol and cholesterol.

Synthesis of plant-derived cholesterol from bisnoralcohol

Currently, the market demand of the non-animal-derived cholesterol is increasing. A novel synthetic route of producing cholesterol was developed through multiple reactions from plant-sourced and commercially available bisnoralcohol (BA). The key reaction conditions, including solvents, reaction temperatures, bases and reducing agents of the route were investigated and optimized. In this straightforward synthetic pathway of cholesterol, most of the reaction steps possess high conversions with average yields of 94%, and the overall yield is up to 74% (5 steps) from the BA. The epicholesterol and were also synthesized. This promising route offers economical and efficient strategies for potential large-scale production of plant-derived cholesterol.

Preparation of Some Unsaturated Side-Chain Derivatives of Cholesterol

Cholesta 5,22(E),25-trien-3β-ol (6), cholesta-5,25-dien-3β-ol (7), 5α-cholest-25-en-3β-ol (8), cholesta-5,22(E),24-triene-3β-ol (9), and cholesta-5,22(E)-dien-3β-ol were prepared from the product obtained by reaction of 3β-acetoxychola-5,23-dien-22-ol with N,O-ketene acetal.