561-63-7

Usage

Uses

Used in Pharmaceutical Industry:
19-HYDROXYCHOLESTEROL is used as a pharmaceutical compound for its cytotoxicity effects. It can be utilized in the development of drugs targeting specific diseases or conditions where cytotoxicity is a desired outcome, such as cancer treatment.
Used in Chemical Research:
As a cholesterol oxidation product, 19-HYDROXYCHOLESTEROL is used as a research compound in the field of chemistry. It can be employed in studying the effects of cholesterol oxidation on cellular processes and the development of new therapeutic strategies.
Used in Cosmetics Industry:
Due to its cytotoxic properties, 19-HYDROXYCHOLESTEROL can be used as an active ingredient in the cosmetics industry, particularly in anti-aging products. It may help in the development of formulations that target the reduction of cellular damage and promote skin health.
Used in Environmental Applications:
19-HYDROXYCHOLESTEROL, being a cholesterol oxidation product, can be used in environmental applications to study the impact of cholesterol oxidation on ecosystems and develop strategies to mitigate the effects of such oxidation processes on the environment.

InChI:InChI=1/C27H46O2/c1-18(2)6-5-7-19(3)23-10-11-24-22-9-8-20-16-21(29)12-15-27(20,17-28)25(22)13-14-26(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3/t19-,21+,22+,23-,24+,25+,26-,27-/m1/s1

Upstream product

• 1104-72-9 (1aR,3aS,3bS,5aR,6R,8aS,8bS,10aR)-6-((R)-1,5-Dimethyl-hexyl)-3a-hydroxymethyl-5a-methyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-10-ol 
• 465-54-3 3,5-cyclocholesterol 
• 57-88-5 cholesterol 
• 604-35-3 Cholesteryl acetate 
• 137436-11-4 methyl 6-oxo-3α,5-cyclo-5α-cholestan-19-oate 
• 3111-05-5 6-oxo-3α,5-cyclo-5α-cholestan-19-oic acid 
• 137436-12-5 (1aR,3aS,3bS,5aR,6R,8aS,8bS,10aR)-6-((R)-1,5-Dimethyl-hexyl)-10-hydroxy-5a-methyl-tetradecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalene-3a-carboxylic acid methyl ester 
• 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 
• 1258-35-1 (3S,5R,6R,8S,9S,10R,13R,14S,17R)-5-bromo-6-hydroxy-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate 
• 750-59-4 3β-acetoxycholest-5-en-19-ol 

Relevant academic research and scientific papers

Sterol synthesis. Preparation and characterization of fluorinated and deuterated analogs of oxygenated derivatives of cholesterol

Oxygenated sterols, including both autoxidation products and sterol metabolites, have many important biological activities. Identification and quantitation of oxysterols by chromatographic and spectroscopic methods is greatly facilitated by the availability of authentic standards, and deuterated and fluorinated analogs are valuable as internal standards for quantitation. We describe the preparation, purification and characterization of 43 oxygenated sterols, including the 4β-hydroxy, 7α-hydroxy, 7β-hydroxy, 7-keto, and 19-hydroxy derivatives of cholesterol and their analogs with 25,26,26,26,27,27,27-heptafluoro (F7) and 26,26,26,27,27,27-hexadeuterio (d6) substitution. The 7α-hydroxy, 7β-hydroxy, and 7-keto derivatives of (25R)-cholest-5-ene-3β,26-diol (1d) and their 16,16-dideuterio analogs were also prepared. These d2-26-hydroxysterols and [16,16-2H2]-(25R)-cholest-5-ene-3β,26-diol (1e) were synthesized from [16,16-2H2]-(25R)-cholest-5-ene-3β,26-diol diacetate (2e), which can be prepared from diosgenin. The highly specific deuterium incorporation at C-16 in 1e and 2e should be useful in mass spectral analysis of 26-hydroxycholesterol samples by isotope dilution methods. The Δ5-3β,7α,26- and Δ5-3β,7β,26-triols were regioselectively oxidized/isomerized to the corresponding Δ4-3-ketosteroids with cholesterol oxidase. Also described are 5,6α-epoxy-5α-cholestan-3β-ol, its 5β,6β-isomer, cholestane-3β,5α,6β-triol, their F7 and d6 derivatives, and d3-25-hydroxycholesterol, which was prepared from 3β-acetoxy-27-norcholest-5-en-25-one (30). The 43 oxysterols and most synthetic intermediates were isolated in high purity and characterized by chromatographic and spectroscopic methods, including mass spectrometry and nuclear magnetic resonance (NMR) spectroscopy. Detailed mass spectral assignments are presented, and 1H NMR stereochemical assignments are derived for the C-19 protons of 19-hydroxysterols and for the side chain protons of 30. Copyright (C) 1999 Elsevier Science Ireland Ltd.

Biosynthetic studies of marine lipids. 39.1 19-norsterols: The course of c-19 methyl elimination

The biosynthesis of 19-norstanols in the Mediterranean sponge, Axinella polypoides, was investigated through the use of radiotracer experiments. It was found that the conversion of cholesterol (7) to 19-nor-5α-chotestan-3β-ol (8) involved oxidation at C-3 with the distribution of the abstracted hydride from the 3α-position of dietary cholesterol into all of the 19-norstanols of the native mixture. Furthermore, while the efficiency of conversion of Δ5-19-oxygenated sterol precursors 19-hydroxycholesterol (9) and 3β-hydroxycholest-5-en-19-oic acid (10) to 8 was low, the efficiency of the conversion of 19-hydroxycholest-4-en-3-one (23) to 8 was high, suggesting that the principal pathway for 19-norstanol biosynthesis involves oxidative isomerization of a dietary Δ5-3β-hydroxy sterol to the δ4-3-ketone before oxidation at C-19. It was also shown that the conversion of cholesterol to 19-nor-5α-cholestan-3β-ol involves the stereospecific loss of the 4β-hydrogen atom. It was further determined that the biological demethylation pathway is suppressed for dietary sterols bearing an unconventional configuration at C-20 in the hydrocarbon side chain.