561-63-7

Basic information

• Product Name: 19-HYDROXYCHOLESTEROL
• Synonyms: 19-HYDROXYCHOLESTEROL;5-CHOLESTEN-3-BETA, 19-DIOL;(3)-Cholest-5-ene-3,19-diol;3,19-Dihydroxycholest-5-ene;Cholest-5-ene-3,19-diol;Cholest-5-ene-3,19-diol, (3b)-;5-Cholestene-3β,19-diol
• CAS NO: 561-63-7
• Molecular Formula: C27H46O2
• Molecular Weight: 402.65
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Steroids
• Mol File: 561-63-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 153-155?C
• Boiling Point: 519.7°Cat760mmHg
• Flash Point: 217°C
• Appearance: /
• Density: 1.03g/cm³
• Vapor Pressure: 5.68E-13mmHg at 25°C
• Refractive Index: 1.537
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 19-HYDROXYCHOLESTEROL(CAS DataBase Reference)
• NIST Chemistry Reference: 19-HYDROXYCHOLESTEROL(561-63-7)
• EPA Substance Registry System: 19-HYDROXYCHOLESTEROL(561-63-7)

Safety Data

• Hazardous Substances Data: 561-63-7(Hazardous Substances Data)

Usage

Description

19-HYDROXYCHOLESTEROL is a metabolite of cholesterol, which is a cholesterol oxidation product with cytotoxicity effects. It is a white solid and is known for its potential applications in various industries due to its unique chemical properties.

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 
• 750-59-4 3β-acetoxycholest-5-en-19-ol 
• 57-88-5 cholesterol 
• 604-35-3 Cholesteryl 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 
• 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 
• 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 
• 3111-05-5 6-oxo-3α,5-cyclo-5α-cholestan-19-oic acid 
• 137436-11-4 methyl 6-oxo-3α,5-cyclo-5α-cholestan-19-oate 

Relevant articles and documents

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.

Steroid series. XVI. The preparation of 3-alpha, 5-alpha-cyclo-6-beta,19-oxidosteroids and its conversion to 19 -oxygenated steroid derivatives.

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