61954-91-4

Usage

Uses

Used in Pharmaceutical Applications:
(1alpha,3beta)-cholesta-5,7-diene-1,3,25-triol is used as a precursor for the production of vitamin D supplements, addressing vitamin D deficiency and its associated health issues.
Used in Skin Health Applications:
(1alpha,3beta)-cholesta-5,7-diene-1,3,25-triol is used as a potential treatment for skin diseases, leveraging its role in vitamin D synthesis and its effects on skin health.
Used in Cosmetics Industry:
(1alpha,3beta)-cholesta-5,7-diene-1,3,25-triol is used as an ingredient in cosmetic products for its potential benefits to skin health and its role in vitamin D production when applied topically and exposed to sunlight.

Upstream product

• 39783-14-7 (5-Cholesten-1α,3β,25-triol)-triacetat 
• 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 
• 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 
• 83872-56-4 1-phenylsulphonyl-3-methyl-3-hydroxybutane 

Downstream Products

• 57102-09-7 [2H]-Pre-1,25-D₃ 
• 96862-25-8 1a,25-Dihydroxytachysterol₃ 
• 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 
• 32222-06-3 calcitriol 

Relevant academic research and scientific papers

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.

Selective capture of 1α,25-(OH)2-previtamin D3 utilizing polymer-supported trialkylsilyl triflate in the synthesis of 1α,25-(OH)2-vitamin D3

Catch and release method utilizing polymer-support was investigated in the separation of 1α,25-(OH)2 pre- and provitamin D3. Polymer-supported alkyldiisopropylsilyl triflate selectively captured the previtamin D3 from a 26:74 mixture of pre- and provitamin D 3 produced by photoisomerization of provitamin D3.

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.

Syntheses of Cholesta-5,7-diene-3β,25-diol and Cholesta-5,7-diene-1α,3β,25-triol

Adducts of 3β-acetoxy- and 1α,3β-diacetoxy-23,24-dinorchola-5,7-dien-22-al (7 and 14) with 4-phenyl-3H-1,2,4-triazole-3,5-dione prepared by the ozonolysis of the corresponding adducts of ergosteryl acetate and 1α-acetoxyergosteryl acetate were transformed

Process for preparation of 1α,25-dihydroxycholecalciferol

1α,25-dihydroxycholecalciferol is prepared by reacting 1,5,7-trien-3β,25-diol with a 1,2,4-triazoline-dione derivative represented by the formula: STR1 wherein R represents an alkyl group or an aryl or substituted-aryl group; reacting the resulting 1,4-cyclic adduct represented by the general formula STR2 wherein R is as defined above, with a peroxide to form a 1α,2α-epoxide compound represented by the general formula STR3 wherein R is as defined above, reducing the so formed compound with a metal hydride to form cholesta-5,7-diene-1α,3β,25-triol, irradiating the so formed compound with ultraviolet rays to form 1α,25-dihydroxyprevitamin D3, isomerizing the so formed previtamin D3, and recovering 1α,25-dihydroxycholecalciferol.