34347-28-9

Basic information

• Product Name: 20E-DEHYDROCHOLESTEROL
• Synonyms: 5,20(22)-CHOLESTADIEN-3-BETA-OL;5,22-CHOLESTADIEN-3-BETA-OL;5,22E-CHOLESTADIEN-3-BETA-OL;22E-DEHYDROCHOLESTEROL;22-DEHYDROCHOLESTEROL;22-DEHYDROCHOLESTEROL (CIS);22-DEHYDROCHOLESTEROL (TRANS);22Z-DEHYDROCHOLESTEROL
• CAS NO: 34347-28-9
• Molecular Formula: C₂₇H₄₄O
• Molecular Weight: 384.64
• Mol File: 34347-28-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 133.5-134.0 °C
• Boiling Point: 479.9°Cat760mmHg
• Flash Point: 208.3°C
• Appearance: /
• Density: 0.99g/cm³
• Vapor Pressure: 3.18E-11mmHg at 25°C
• Refractive Index: 1.535
• PKA: 15.03±0.70(Predicted)
• CAS DataBase Reference: 20E-DEHYDROCHOLESTEROL(CAS DataBase Reference)
• NIST Chemistry Reference: 20E-DEHYDROCHOLESTEROL(34347-28-9)
• EPA Substance Registry System: 20E-DEHYDROCHOLESTEROL(34347-28-9)

Safety Data

• Hazardous Substances Data: 34347-28-9(Hazardous Substances Data)

Usage

General Description

20E-Dehydrocholesterol, also known as provitamin D3, is a cholesterol precursor that is found in the skin of humans and other animals. It plays a crucial role in the synthesis of vitamin D when exposed to ultraviolet light. Upon UV exposure, 20E-dehydrocholesterol is converted into pre-vitamin D3, which then undergoes further chemical reactions in the body to produce active vitamin D. This process is essential for maintaining healthy bones and teeth, as well as for supporting the immune system and overall health. Additionally, 20E-dehydrocholesterol is also used in the production of certain drugs and as a precursor for the synthesis of cholesterol and steroid hormones in the body.

InChI:InChI=1/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h6,8-9,18-19,21-25,28H,7,10-17H2,1-5H3/b8-6+/t19-,21+,22+,23?,24+,25+,26+,27-/m1/s1

Upstream product

• 28322-40-9 isoamyltriphenylphosphonium bromide 
• 3986-89-8 (20S)-3-oxopregn-4-ene-20-carboxaldehyde 
• 40736-33-2 (20S)-20-hydroxymethylpregn-4-en-3-one 
• 83-48-7 Stigmasterol 
• 107-84-6 1-chloro-3-methylbutane 
• 53906-49-3 3β-ol-23,24-bisnor-chol-5-en-22-al hemihydrochloride 
• 53139-42-7 stigmasteryl tosylate 
• 10211-88-8 (20S)-3β-acetoxybisnorchol-5-en-22-al 
• 80925-45-7 (22E,25R,S)-N,N-dimethyl-3β-acetoxycholesta-5,22-dien-26-amide 
• 80907-93-3 (22E,25R,S)-26-(dimethylamino)cholesta-5,22-dien-3β-ol N-oxide 
• 80907-91-1 (20S,22R,S)-3β-acetoxychola-5,23-dien-22-ol 
• 80907-92-2 (22E,25R,S)-26-(dimethylamino)cholesta-5,22-dien-3β-ol 
• 76719-23-8 (22E)-cholest-5,22-diene-3β-tetrahydropyranyloxy-26-oic acid ethyl ester 
• 77736-44-8 2-[(3S,8S,9S,10R,13R,14S,17R)-17-((E)-(R)-1,5-Dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-tetrahydro-pyran 

Downstream Products

• 57-88-5 cholesterol 
• 86270-28-2 C₃₄H₅₀O₃S 
• 86794-55-0 (23R)-cholest-5-ene-3β,23-diol dibenzoate 
• 17955-01-0 (22S)-22-hydroxycholesterol dibenzoate 
• 64110-88-9 (22E)-22,23-dehydrocholesterol benzoate 

Relevant articles and documents

Methods for preparing cholesterol, and derivatives and analogs thereof

The present invention relates to the field of pharmaceutical chemistry, and in particular to methods of preparing cholesterol,and derivatives and analogs thereof. The cholesterol derivatives include, but not limited to, 7-dehydrocholesterol, 25-hydroxycholesterol, 25- hydroxy7dehydrocholesterol and ergosterol. In the invention, phytosterol can be used as a raw material to prepare the compound shown in the formula I through microbial conversion, and then cholesterol and the derivatives and analogues thereof are prepared.

Preparation of Some Unsaturated Side-Chain Derivatives of Cholesterol

Cholesta 5,22(E),25-trien-3β-ol (6), cholesta-5,25-dien-3β-ol (7), 5α-cholest-25-en-3β-ol (8), cholesta-5,22(E),24-triene-3β-ol (9), and cholesta-5,22(E)-dien-3β-ol were prepared from the product obtained by reaction of 3β-acetoxychola-5,23-dien-22-ol with N,O-ketene acetal.

Synthesis of sterols with modified side chains

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