61954-91-4

Basic information

• Product Name: (1alpha,3beta)-cholesta-5,7-diene-1,3,25-triol
• Synonyms: Cholesta-5,7-diene-1,3,25-triol, (1alpha,3beta)-
• CAS NO: 61954-91-4
• Molecular Formula: C₂₇H₄₄O₃
• Molecular Weight: 416.6365
• EINECS: 612-815-4
• Mol File: 61954-91-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 561.9°C at 760 mmHg
• Flash Point: 238.4°C
• Density: 1.09g/cm³
• Vapor Pressure: 5.75E-15mmHg at 25°C
• Refractive Index: 1.561
• CAS DataBase Reference: (1alpha,3beta)-cholesta-5,7-diene-1,3,25-triol(CAS DataBase Reference)
• NIST Chemistry Reference: (1alpha,3beta)-cholesta-5,7-diene-1,3,25-triol(61954-91-4)
• EPA Substance Registry System: (1alpha,3beta)-cholesta-5,7-diene-1,3,25-triol(61954-91-4)

Safety Data

• Hazardous Substances Data: 61954-91-4(Hazardous Substances Data)

Usage

General Description

(1alpha,3beta)-cholesta-5,7-diene-1,3,25-triol, also known as 7-dehydrocholesterol, is a type of cholesterol derivative that is an essential precursor for the production of vitamin D in the skin. It is a sterol compound with a unique structure that includes a double bond between the 5th and 7th carbon atoms, as well as hydroxyl groups at the 1st, 3rd, and 25th positions. This chemical plays a crucial role in the synthesis of vitamin D when exposed to UVB radiation in the skin, and deficiency in 7-dehydrocholesterol can lead to vitamin D deficiency and related health issues. Additionally, it has been studied for its potential pharmaceutical applications, such as in the treatment of skin diseases and as a precursor for the production of vitamin D supplements.

Upstream product

• 57102-09-7 [2H]-Pre-1,25-D₃ 
• 1384584-77-3 1α,3β-dihydroxy-25-trimethylsilyloxycholesta-5,7-diene 
• 133856-07-2 1α,3β-dihydroxy-22-tosyloxy-23,24-bisnorchola-5,7-diene 
• 126771-82-2 C₃₃H₄₄O₉S 
• 69540-69-8 1α,2α-Epoxycholest-5-en-3β,25-diol 
• 50392-32-0 1α,3β,25-Trihydroxy-cholest-5-ene 
• 39783-14-7 (5-Cholesten-1α,3β,25-triol)-triacetat 
• 125315-66-4 23-phenylsulfonyl-1α,3β,25-tris(tetrahydropyranyloxy)cholesta-5,7-diene 
• 125315-63-1 1α,3β-bis(tetrahydropyranyloxy)-23,24-dinorchola-5,7-dien-22-ol p-toluenesulfonate 
• 125315-65-3 22-iodo-1α,3β-bis(tetrahydropyranyloxy)-23,24-dinorchola-5,7-diene 
• 125315-62-0 1α,3β-bis(tetrahydropyranyloxy)-23,24-dinorchola-5,7-dien-22-ol 
• 119950-09-3 1α-hydroxyergosterol 
• 125315-53-9 22-Oxo-5α,8α-(4-phenyl-3,5-dioxo-1,2,4-triazolidine-1,2-diyl)-23,24-dinor-6-cholene-1α,3β-diyl diacetate 
• 125315-55-1 22-hydroxy-5α,8α-(4-phenyl-3,5-dioxo-1,2,4-triazolidine-1,2-diyl)-23,24-dinorchol-6-ene-1α,3β-diol 1,3-diacetate 

Downstream Products

• 32222-06-3 calcitriol 
• 98728-28-0 (4-Azido-2-nitro-phenylamino)-acetic acid (1R,3S)-3-hydroxy-5-[2-[(1R,3aS,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester 
• 73809-41-3 (5Z,7E,1S,3R)-3-acetoxy-9,10-seco-5,7,10⁽¹⁹⁾-cholestatriene-1,25-diol 
• 98728-26-8 1α-tert-butyldimethylsilylether of 1α-25-dihydroxyvitamin D₃ 
• 57102-09-7 [2H]-Pre-1,25-D₃ 
• 96862-25-8 1a,25-Dihydroxytachysterol₃ 

Relevant articles and documents

Continuous-flow synthesis of activated vitamin D3 and its analogues

An efficient, two-stage, continuous-flow synthesis of 1α,25-(OH) 2-vitamin D3 (activated vitamin D3) and its analogues was achieved. The developed method afforded the desired products in satisfactory yields using a high-intensity and economical light source, i.e., a high-pressure mercury lamp. In addition, our method required neither intermediate purification nor high-dilution conditions. The Royal Society of Chemistry 2012.

An effective procedure for the synthesis of 1α,25-dihydroxy-cholecalciferol (calcitriol) starting with 1α,3β, 25-trihydroxy-cholesta-5,7-diene (pro-calcitriol)

In order to develop an effective synthesis of the important vitamin D metabolite 1α,25-(OH)2-cholecalciferol (calcitriol) 5a starting with pro-calcitriol 1a the influence of reaction temperature and degree of turnover of 1a to the compositions of the photoproducts at irradiation in a 500 ml photoreactor were investigated. The combination of the highly photostable filter solution consisting of 2,7-dimethyl-3,6-diaza-cyclohepta-1,6-diene-tetrafluoroborate and biphenyl in ethanol realizes the double wavelength irradiation in the range of 290 to 300 nm and>330 nm resulting in a highly amount of the desired pre-calcitriol 2a. The reversible photoisomers of pre-calcitriol 2a 1α,25-(OH)2-lumisterol3 4a and 1α,25-(OH)2-tachysterol3 3a were isolated from an irradiation mixture in pure form by means of an appropriate combination of flash-chromatography, MPLC and preparative HPLC, respectively. The isomers 2a, 3a and 4a were characterized chromatographically and spectroscopically. Photoisomerization of 1a at -45°C using the filter solution mentioned above and recycling all reversible photoisomers resulted in highly pure 5a after thermally induced isomerization of 2a isolated from the irradiation mixture by means of flash-chromatography on Ag+-impregnated silica with a yield of 68%. Johann Ambrosius Barth 1996.

Studies in 1α-hydroxyl derivatives of vitamin D3. I. Syntheses of 1α-hydroxyvitamin D3 and 1α,25-dihydroxyvitamin D3

-