13200-77-6

Basic information

• Product Name: 19-HYDROXYCHOLESTENONE
• Synonyms: 19-HYDROXYCHOLESTENONE;4-CHOLESTEN-19-OL-3-ONE
• CAS NO: 13200-77-6
• Molecular Formula: C₂₇H₄₄O₂
• Molecular Weight: 400.64
• Mol File: 13200-77-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 19-HYDROXYCHOLESTENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 19-HYDROXYCHOLESTENONE(13200-77-6)
• EPA Substance Registry System: 19-HYDROXYCHOLESTENONE(13200-77-6)

Safety Data

• Hazardous Substances Data: 13200-77-6(Hazardous Substances Data)

Usage

Chemical structure

A steroid compound with a hydroxyl group at the 19th carbon position.

Derivative

A derivative of cholesterol.

Biosynthesis

Involved in the biosynthesis of steroid hormones in the body.

Biological activities

Exhibits potential biological activities, such as anti-inflammatory properties and regulation of lipid metabolism.

Biomarker

Identified as a biomarker for certain diseases, including Niemann-Pick disease type C.

Disease association

Niemann-Pick disease type C, a rare inherited lipid storage disorder.

Research status

Further research is needed to fully understand the physiological roles and potential therapeutic applications of 19-Hydroxycholestenone.

Upstream product

• 749-00-8 6β,19-Oxido-Δ⁴-cholestenon-(3) 
• 90361-07-2 C₂₇H₄₃BrO₂ 
• 1258-07-7 (3S,5R,6R,8S,9S,10R,13R,14S,17R)-5-bromo-13-methyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-6,10-(epoxymethano)cyclopenta[a]phenanthren-3-yl acetate 
• 14908-10-2 5-Bromo-6β,19-epoxy-5α-cholestan-3β-ol 
• 1261029-94-0 19-O-(2-acetylamino-2-deoxy-β-D-glucopyranosyl)-19-hydroxy-cholest-4-en-3-one 

Downstream Products

• 21515-60-6 19-acetoxy-4-cholesten-3-one 
• 115884-06-5 4-Cholestene-3β,19-diol 3-Acetate 19-p-Toluenesulphonate 
• 115884-04-3 4-Cholestene-3α,19-diol 3-Acetate 19-p-Toluenesulphonate 
• 115884-05-4 4-Cholestene-3β,19-diol 19-p-Toluenesulphonate 
• 115884-03-2 4-Cholestene-3α,19-diol 19-p-Toluenesulphonate 
• 115884-22-5 <19-2H2>-4β,5-Cyclopropano-5β-cholestane-3β,19-diol 3-Acetate 19-p-Toluenesulphonate 
• 115884-21-4 <19-2H2>-4β,5-Cyclopropano-5β-cholestane-3β,19-diol 19-p-Toluenesulphonate 
• 96772-71-3 19-Hydroxy-4-cholesten-3-one 19-p-Toluenesulphonate 

Relevant articles and documents

Structure and biological evaluation of novel cytotoxic sterol glycosides from the marine red alga Peyssonnelia sp.

Bioactivity-guided fractionation of the extract from a Fijian red alga Peyssonnelia sp. led to the isolation of two novel sterol glycosides 19-O-β-d-glucopyranosyl-19-hydroxy-cholest-4-en-3-one (1) and 19-O-β-d-N-acetyl-2-aminoglucopyranosyl-19-hydroxy-cholest-4-en-3-one (2), and two known alkaloids indole-3-carboxaldehyde (3) and 3-(hydroxyacetyl)indole (4). Their structures were characterized by 1D and 2D NMR and mass spectral analysis. The sterol glycosides inhibited cancer cell growth with mean IC 50 values (for 11 human cancer cell lines) of 1.63 and 1.41 μM for 1 and 2, respectively. The most sensitive cancer cell lines were MDA-MB-468 (breast) and A549 (lung), with IC50's in of 0.71-0.97 μM for 1 and 2. Modification of the sterol glycoside structures revealed that the α,β-unsaturated ketone at C-3 and oxygenation at C-19 of 1 and 2 are crucial for anticancer activity, whereas the glucosidic group was not essential but contributed to enhanced activity against the most sensitive cell lines.

Hypervalent Organoiodine Compounds: Radical Fragmentation of Oxabicyclic Hemiacetals. Convenient Synthesis of Medium-sized and Spiro Lactones

Photolysis of steroidal models of oxabicyclic hemiacetals such as 2-oxabicyclodecan-1-ol, 9-oxabicyclononan-1-ol and 2-oxabicyclooctan-1-ol, in the presence of (diacetoxyiodo)benzene and iodine afforded, through ring expansion, ten-, nine- and eight-membered lactones, respectively.Spiro lactones of dihydropyran-5-spirocyclohexan-2(3H)-one and dihydrofuran-4-spirocyclohexan-2(3H)-one types were obtained by photolysis of steroidal models of 2-oxabicyclooctan-1-ol and 7-oxabicyclooctan-1-ol, respectively.