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(25R)-cholest-5-ene-3β,26-diol

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Origin: China

Cas No: 20380-11-4

Specification: 99%min

Min order Quantity: 1 /kg

Supply Ability: 80 mt/month

Lead time: 7 days for OEM, 3 days for ready goods

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CAS No.: 20380-11-4 Formula: C27H46O2 Molecular Weight: 402.65300

Description

27-Hydroxycholesterol (27-HC) is an endogenous oxysterol with multiple biological functions, including activity as a selective estrogen receptor modulator (SERM) (a mixed, tissue-specific agonist-antagonist of the estrogen receptor (ER)) and as an agonist of the liver X receptor (LXR). It is a metabolite of cholesterol that is produced by the enzyme CYP27A1.
A link between high cholesterol and breast cancer has been identified, and it has been proposed that this is due to 27-HC production by CYP27A1. Because of its estrogenic action, 27-HC stimulates the growth of ER-positive breast cancer cells, and has been implicated in limiting the effectiveness of aromatase inhibitors in the treatment of breast cancer. As such, identified CYP27A1 inhibitors, including the marketed drugs anastrozole, fadrozole, bicalutamide, dexmedetomidine, ravuconazole, and posaconazole, have been proposed as potential adjuvant therapies in ER-positive breast cancer.

Basic Info

Chemical Name	(25R)-cholest-5-ene-3β,26-diol
Synonyms	(25R)-cholest-5-ene-3beta,26-diol; 5,25R-Cholesten-3beta,26-diol;
CAS No.	20380-11-4
Molecular Formula	C27H46O2
Molecular Weight	402.65300
PSA	40.46000
LogP	6.36110

Properties

Density	1.03
Boiling Point	517.1ºC at 760 mmHg
Melting Point	172 - 173 °C
Flash Point	215.6ºC
Refractive Index	1.537
Vapor Pressure	7.43E-13mmHg at 25°C

Synthesis Route

(20R)-20-(2-hydroxyethyl)-5-pregnen-3β-ol tetrahydropyranyl ether→(25R)-cholest-5-ene-3β,26-diol
→(25R)-cholest-5-ene-3β,26-diol
(25R)-cholest-5-en-3β,26-diol 26-(2'-tetrahydropyranyl) ether→(25R)-cholest-5-ene-3β,26-diol

Precursor

(25R)-cholest-5-en-3β,26-diol 26-(2'-tetrahydropyranyl) ether
(25R)-cholest-5-ene-3β,16β,26-triol 3β,26-dipivalate
(20R)-20-(2-hydroxyethyl)-5-pregnen-3β-ol tetrahydropyranyl ether
(3S,8S,9S,10R,13R,14S,17R)-17-((2R)-7-hydroxy-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

Downstream Product

(25R)-5α-cholestane-3β,26-diol 26-pivalate
(25R)-5α-cholest-14-ene-3α,26-diol 3α,26-diacetate
(25R)-3-oxo-5α-cholestan-26-oic acid
(25R)-26-chloro-4,4-dimethyl-5α-cholesta-8,14-dien-3β-ol

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