434-16-2

Basic information

• Product Name: 7-Dehydrocholesterol
• Synonyms: (3)-7-Dehydrochlesterol;(3beta)-Cholesta-5,7-dien-3-ol;(3-beta)-cholesta-7-dien-3-ol;(3beta)-cholesta-7-dien-3-ol;3-Hydroxycholesta-5,7-diene;5,7-Cholestandien-3.beta.-ol;5,7-Cholestandien-3beta-ol;7,8-Didehydrocholesterol
• CAS NO: 434-16-2
• Molecular Formula: C27H44O
• Molecular Weight: 384.64
• EINECS: 207-100-5
• Product Categories: Pharmaceutical Raw Materials;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 434-16-2.mol
• Article Data: 27

Chemical Properties

• Melting Point: 148-152 °C(lit.)
• Boiling Point: 451.27°C (rough estimate)
• Flash Point: 212.294 °C
• Appearance: white to off-white fine crystalline powder
• Density: 0.9717 (rough estimate)
• Vapor Pressure: 8.08E-12mmHg at 25°C
• Refractive Index: 1.5100 (estimate)
• Storage Temp.: −20°C
• Solubility: Chloroform (Sparingly), DMSO (Slightly, Heated, Sonicated), Ethyl Acetate (Sligh
• PKA: 14.91±0.70(Predicted)
• Water Solubility: Insoluble
• Stability: Light Sensitive
• Merck: 13,2887
• BRN: 2224615
• CAS DataBase Reference: 7-Dehydrocholesterol(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Dehydrocholesterol(434-16-2)
• EPA Substance Registry System: 7-Dehydrocholesterol(434-16-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: FZ5650000
• F: 8-10-23
• Hazardous Substances Data: 434-16-2(Hazardous Substances Data)

Usage

Description

7-Dehydrocholesterol (7-DHC) is an immediate precursor of cholesterol, playing a crucial role in the last step of cholesterol biosynthesis. It is reduced to cholesterol by the enzyme 3β-hydroxysterol-Δ7-reductase (DHCR7). Accumulation of 7-DHC occurs in Smith-Lemli-Opitz syndrome (SLOS), a disorder characterized by a mutation in the DHCR7 gene, decreased cholesterol levels in bodily tissues and fluids, and various developmental issues. Additionally, 7-DHC is a provitamin that can be converted to vitamin D3 by ultraviolet-B (UVB) light exposure in human skin.

Uses

Used in Vitamin D3 Production:
7-Dehydrocholesterol is used as a vitamin precursor for the production of vitamin D3. It is converted to vitamin D3 by the action of sunlight or ultraviolet irradiation, which is synthesized in the skin of animals and humans.
Used in Cholesterol Biosynthesis:
7-Dehydrocholesterol is used as an immediate precursor in the cholesterol biosynthesis process, being reduced to cholesterol by the enzyme 3β-hydroxysterol-Δ7-reductase (DHCR7).
Used in Diagnostics for Smith-Lemli-Opitz Syndrome:
7-Dehydrocholesterol is used as a diagnostic marker for Smith-Lemli-Opitz syndrome. Blood and tissue samples from infants with SLO syndrome contain reduced amounts of cholesterol and greatly increased concentrations of 7-dehydrocholesterol and its isomer 8-dehydrocholesterol.
Used as an Internal Standard in Sterol Analysis:
7-Dehydrocholesterol has been used as an internal standard to determine sterols, aiding in the accurate measurement and analysis of various sterol compounds in biological samples.

Biochem/physiol Actions

Down-regulates cholesterol biosynthesis in cultured Smith-Lemi-Opitz syndrome skin fibroblasts.

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/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1

Upstream product

• 5226-01-7 Lumisterol₃ 
• 54201-67-1 3-β-acetoxycholest-5-en-7-one tosylhydrazone 
• 107-82-4 i-pentyl bromide 
• 40736-33-2 (20S)-20-hydroxymethylpregn-4-en-3-one 
• 19707-16-5 22-tosyloxy-23,24-dinorchol-4-en-3-one 
• 110-89-4 piperidine 
• 123-91-1 1,4-dioxane 
• 6038-38-6 3β,7β-bis-benzoyloxy-cholest-5-ene 
• 108-48-5 2,6-dimethylpyridine 
• 57566-18-4 7α-bromocholesterol acetate 
• 108-75-8 2,4,6-trimethyl-pyridine 
• 604-35-3 Cholesteryl acetate 
• 604-32-0 cholesterol benzoate 
• 110-54-3 hexane 

Downstream Products

• 1059-86-5 7-Dehydrocholesteryl acetate 
• 51982-45-7 Δ^5,7,9-cholestatrien-3β-ol 
• 67-97-0 cholecalciferol 
• 434-16-2 lumisterol₃ 
• 1173-13-3 previtamin D₃ 
• 1173-13-3 tachysterol₃ 
• 21307-05-1 previtamin D₂ 
• 474-69-1 lumisterol 
• 115-61-7 Tachysterol 
• 1173-13-3 previtamin D₃ 
• 67-97-0 vitamin D₃ 
• 17592-07-3 tachysterol₃ 
• 5226-01-7 Lumisterol₃ 
• 10346-43-7 Lumisterol₃ 

Relevant articles and documents

Oxidation of cholesterol by a biomimetic oxidant, cetyltrimethylammonium dichromate

The oxidation of cholesterol by cetyltrimethylammonium dichromate (CTADC) in dichloromethane (DCM) yielded 7-dehydrocholesterol, while with addition of acetic acid in DCM the product was found to be 5-cholesten-3-one. The kinetics of oxidation of cholesterol by CTADC in DCM, in the presence of acid, was investigated with change in [acid], [cholesterol], [CTADC], [surfactant], temperature, and solvents. The reaction was found to be first order with acetic acid and fractional order with CTADC and cholesterol. Michaelis-Menten-type kinetics was observed with respect to cholesterol. The solvent isotope effect was found to be k(D2O)/k(H2O) = 0.72. The observed experimental data suggest that the reaction occurs in reversed micellar system, akin to an enzymatic environment, and the reaction path involves the intermediate formation of an ester complex, which undergoes decomposition to give the product.

ORGANIC SOLVENT NANOFILTRATION OF 7-DEHYDROCHOLESTEROL OR 25-HYDROXY-7-DEHYDROCHOLESTEROL OR THEIR OH PROTECTED FORMS

The present invention relates to the purification of 7-dehydrocholesterol or 25-hydroxy-7-dehydrocholesterol or their OH-protected forms, respectively. It has been found that the process using organic solvent nanofiltration allows an efficient reduction of the amount of a new higher molecular compound which is formed in a 5 new synthesis process of of 7-dehydrocholesterol or 25-hydroxy-7-dehydrocholes- terol or their OH-protected forms in small amounts. Said new higher molecular compound can be used as colorant.

Preparation method of 7-dehydrocholesterol for production of vitamin D3

The invention particularly discloses a preparation method of 7-dehydrocholesterol for production of vitamin D3. The preparation method comprises the following steps: an esterification reaction, a bromination reaction, a debromination reaction and a saponification hydrolysis reaction. The esterification reaction comprises the following steps: adding cholesterol, an acid-binding agent and a solid catalyst into petroleum ether, carrying out heating to 45-50 DEG C in a nitrogen atmosphere, dropwise adding benzoyl chloride, performing heating to 78-82 DEG C after dropwise adding, conducting stirring for a reaction for 3-5 hours, adding distilled water to quench the reaction, performing filtering to obtain filter residues and a filtrate, extracting the filter residues with distilled water, concentrating an oil layer, then adding acetone, carrying out a reflux reaction for 30-40 minutes, conducting cooling to 20-30 DEG C, and performing filtering to obtain cholesterol benzoate; and soaking, filtering and drying the filter residues to obtain a solid desiccant, and repeatedly using the solid desiccant. The method has the advantage of facilitating cyclic utilization of the catalyst.