705926-28-9

Basic information

• Product Name: (22E)-3β-hydroxyergosta-8(14),22-dien-15-one
• CAS NO: 705926-28-9
• Molecular Weight: 412.656
• Mol File: 705926-28-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (22E)-3β-hydroxyergosta-8(14),22-dien-15-one(CAS DataBase Reference)
• NIST Chemistry Reference: (22E)-3β-hydroxyergosta-8(14),22-dien-15-one(705926-28-9)
• EPA Substance Registry System: (22E)-3β-hydroxyergosta-8(14),22-dien-15-one(705926-28-9)

Safety Data

• Hazardous Substances Data: 705926-28-9(Hazardous Substances Data)

Upstream product

• 71242-49-4 (3S,5S,10S, 13R,17R)-17-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-10,13-dimethyl-2,3,4,5,6,7,10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate 
• 57-87-4 ergosta-5,7,22-triene-3β-ol 
• 4356-12-1 (22E)-3β-acetoxy-5α-ergosta-7,14,22-triene 
• 705926-27-8 3β-acetoxy-24-methyl-14α,15α-oxido-5α-cholesta-7,22-diene 
• 87530-82-3 (3S,5S,9R,10S,13R,17R)-17-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-10,13-dimethyl-15-oxo-2,3,4,5,6,7,9,10,11,12,13,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate 
• 36071-76-8 (3β,5α,22E)-3-(benzoyloxy)ergosta-8(14),22-dien-15-one 

Relevant articles and documents

Synthesis of new 15-ketosterol analogues from ergosterol

Ergosteryl acetate was converted through three stages into 3β-acetoxy-24-methyl-5α-cholesta-8(14),22-diene-15-one in 32% overall yield. The product was transformed to 3β-hydroxy-24-methyl-5α- cholesta-8(14),22-diene-15-one, 3α-hydroxy-24-methyl-5α-cholesta- 8(14),22-diene-15-one, and 24-methyl-5α-cholesta-8(14),22-diene-3,15- dione. The compounds were characterized by 1H and 13C NMR spectra.

Novel side chain modified Δ8(14)-15-ketosterols

Synthesis of five novel Δ8(14)-15-ketosterols comprising modified side chains starting from ergosterol is described. Ergosteryl acetate was converted into (22E)-3β-acetoxy-5α-ergosta-8(14),22-dien-15-one through three stages in 32% overall yield; further transformations of the product obtained led to (22E)-3β-hydroxy-5α-ergosta-8(14),22-dien-15-one, (22S,23S)-3β-hydroxy-22,23-oxido-5α-ergost-8(14)-en-15-one, (22R,23R)-3β-hydroxy-22,23-oxido-5α-ergost-8(14)-en-15-one, (22R,23R)-5α-ergost-8(14)-en-15-on-3β,22,23-triol and (22R,23R)-3β-hydroxy-22,23-isopropylidenedioxy-5α-ergost-8(14)-en-15-one. New Δ8(14)-15-ketosterols were evaluated for their cytotoxicity and effects on sterol biosynthesis in human hepatoma Hep G2 cells in comparison with known 3β-hydroxy-5α-cholest-8(14)-en-15-one. Among the compounds tested, (22R,23R)-3β-hydroxy-22,23-oxido-5α-ergost-8(14)-en-15-one was found to be the most potent inhibitor of sterol biosynthesis (IC50 = 0.6 ± 0.2 μM), whereas (22R,23R)-5α-ergost-8(14)-en-15-on-3β,22,23-triol exhibited the highest cytotoxicity (TC50 = 12 ± 3 μM at a 24 h incubation).

Improved preparation of (3β,5α,14α)-3-hydroxy-14-methylcholest-7-en-15-one. Synthesis of ergostenone and 20α-(hydroxymethyl)pregnenone analogues

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