Cholesta-5,7-dien-3beta-ol

Base Information

• Chemical Name: Cholesta-5,7-dien-3beta-ol
• CAS No.: 434-16-2
• Molecular Formula: C27H44O
• Molecular Weight: 384.646
• Hs Code.: 29061990
• NSC Number: 18159
• Wikidata: Q105270121
• Mol file: 434-16-2.mol

Synonyms:.DELTA.7-Cholesterol;Cholesterol, 7-dehydro-;.DELTA.5,7-Cholesterol;Cholesta-5,7-dien-3-beta-ol;5,7-Cholestandien-3.beta.-ol;(3.beta.)-Cholesta-5,7-dien-3-ol;Cholesta-5,7-dien-3.beta.-ol;NSC-18159;Cholesta-5,7-dien-3-ol, (3beta)-;Cholesta-5,7-dien-3-ol, (3-beta)-;Cholesta-5,7-dien-3-ol, (3.beta.)-;SCHEMBL287700;Cholesta-5,7-dien-3-.beta.-ol;NSC18159;AKOS015916288;LS-53098;FT-0621393;FT-0670878;FT-0696900;17-(1,5-DIMETHYL-HEXYL)-10,13-DIMETHYL-DODECAHYDRO-CYCLOPENTA(A)PHENANTHREN-3-OL

Chemical Property of Cholesta-5,7-dien-3beta-ol

Chemical Property:

• Appearance/Colour: white to off-white fine crystalline powder
• Vapor Pressure: 8.08E-12mmHg at 25°C
• Melting Point: 148-152 °C(lit.)
• Refractive Index: 1.535
• Boiling Point: 493.744 °C at 760 mmHg
• PKA: 14.91±0.70(Predicted)
• Flash Point: 212.294 °C
• PSA: 20.23000
• Density: 1.002 g/cm³
• LogP: 7.30880
• Storage Temp.: −20°C
• Solubility.: Chloroform (Sparingly), DMSO (Slightly, Heated, Sonicated), Ethyl Acetate (Sligh
• Water Solubility.: Insoluble
• XLogP3: 8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 384.339216023
• Heavy Atom Count: 28
• Complexity: 643

Purity/Quality:

99%, ^*data from raw suppliers

(3β)-7-DehydroCholesterol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2=CC=C4C3(CCC(C4)O)C)C
• Description: 7-dehydro Cholesterol (7-DHC) is an immediate precursor of cholesterol. It is reduced to cholesterol by the enzyme 3β-hydroxysterol-Δ7-reductase (DHCR7) in the last step of cholesterol biosynthesis. 7-DHC accumulates in Smith-Lemli-Opitz syndrome (SLOS), a disorder characterized by a mutation in the DHCR7 gene and decreased cholesterol levels in bodily tissues and fluids, as well as microcephaly, intellectual disability, and distinctive dysmorphic features. It is highly susceptible to free radical oxidation, giving rise to several oxysterols that may be involved in the pathogenesis of SLOS. 7-DHC levels are increased in brain, liver, and serum in a rat model of SLOS induced by the DHCR7 inhibitor AY 9944 . 7-DHC is a provitamin that is converted to vitamin D3 by ultraviolet-B (UVB) light in a human skin equivalent system and in isolated human skin samples.
• Uses: A vitamin precursor. Vitamin D3 is produced by the action of sunlight or ultraviolet irradiation from the precursor, 7-dehydrocholesterol (7-DC), that is synthesized in the skin of animals and humans. In most tissues of the body, 7-dehydrocholesterol is the immediate precursor of cholesterol. It is reduced to cholesterol by the enzyme 3β-hydroxysterol-Δ7-reductase (DHCR7) in the last step of cholesterol biosynthesis. 7-DHC accumulates in Smith-Lemli-Opitz syndrome (SLOS), a disorder characterized by a mutation in the DHCR7 gene and decreased cholesterol levels in bodily tissues and fluids, as well as microcephaly, intellectual disability, and distinctive dysmorphic features. It is highly susceptible to free radical oxidation, giving rise to several oxysterols that may be involved in the pathogenesis of SLOS. 7-DHC levels are increased in brain, liver, and serum in a rat model of SLOS induced by the DHCR7 inhibitor AY 9944. 7-DHC is a provitamin that is converted to vitamin D3 by ultraviolet-B (UVB) light in a human skin equivalent system and in isolated human skin samples. 7-Dehydrocholesterol (7-DHC), a 5,7-conjugated diene sterol is a biosynthetic precursor of cholesterol. It helps in the production of vitamin D3 when exposed to ultraviolet B (UVB) radiation. 7-Dehydrocholesterol has been used as an internal standard to determine sterols. 7-dehydrocholesterol is used in the diagnosis of Smith-Lemli-Opitz syndrome. Blood and tissue of infants with Smith- Lemli-Opitz (SLO) syndrome contain reduced amounts of cholesterol and greatly increased concentrations of 7-dehydrocholesterol and of its isomer 8-dehydrocholesterol. A vitamin D3 precursor.

Technology Process of Cholesta-5,7-dien-3beta-ol

There total 83 articles about Cholesta-5,7-dien-3beta-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

7-Dehydrocholesteryl acetate (1059-86-5) → 7-dehydrocholesterol (434-16-2)

Guidance literature:

With alkali metal hydroxide; In methanol; at 50 ℃; Large scale;

Reference yield: 88.0%

3β-tert-butyldimethylsilyloxy-cholesta-5,7-diene (207221-59-8) → 7-dehydrocholesterol (434-16-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2.5h; Inert atmosphere;

Reference yield: 68.0%

7-α,β-bromocholesteryl 3β-acetate (61949-57-3) → cholest-4,6-diene-3-ol (14214-69-8) + 7-dehydrocholesterol (434-16-2)

Guidance literature:

With 2,4,6-trimethyl-pyridine; tetrabutylammomium bromide; In acetic acid butyl ester; at 125 ℃; for 0.166667h; Yields of byproduct given;

DOI:10.1246/bcsj.59.3702

upstream raw materials:

piperidine

1,4-dioxane

3β,7β-bis-benzoyloxy-cholest-5-ene

2,6-dimethylpyridine

Downstream raw materials:

3β-benzoyloxycholesta-5,7-diene

cholesta-4,7-dien-3-one

cholecalciferol

lumisterol₃

Refernces

• 1、 -. "Preparation method of 7-dehydrocholesterol for production of vitamin D3". . . Retrieved 2021/04/07.
• 2、 -. "PREPARATION OF 7-DEHYDROCHOLESTEROL USING SPECIFIC AROMATIC SOLVENTS". Page/Page column 16. . Retrieved 2021/10/30.