57651-82-8

Usage

Type

Active form of vitamin D3

Function

Regulates calcium and phosphate levels in the body, maintains bone health, supports the immune system, has anti-inflammatory and anti-cancer properties

Synthesis

Synthesized in the kidneys

Uses

Used as a pharmaceutical agent to treat conditions such as osteoporosis, hypoparathyroidism, and renal osteodystrophy

Research

Being researched for potential in the treatment of various other diseases, including autoimmune disorders and certain types of cancer.

Upstream product

• 434-16-2 7-dehydrocholesterol 
• 61625-50-1 cyclovitamin D₃ 
• 61625-50-1 2-[(1R,3aS,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-1-((S)-2-methylene-bicyclo[3.1.0]hex-1-yl)-ethanol 
• 98854-76-3 2-[(1R,3aS,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-1-((1R,5R)-2-methylene-bicyclo[3.1.0]hex-1-yl)-ethanol 
• 66251-18-1 Grundmann's ketone 
• 93490-16-5 (1R,3aR,7aR)-4-Dibromomethyl-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-4-ol 
• 101143-32-2 8-bromomethylenedes-AB-cholestane 
• 93489-97-5 (+)-(1R,5R)-2-methylenebicyclo<3.1.0>hexane-1-ylmethanol 
• 93601-52-6 (+)-2-methylenebicyclo<3.1.0>hexane-1-carbaldehyde 
• 88908-86-5 (+/-)-1-formyl-2-methylenebicyclo<3.1.0>hexane 
• 88908-87-6 (+/-)-methyl 2-methylenebicyclo<3.1.0>hexane-1-carboxylate 
• 93489-97-5 (+/-)-2-methylenebicyclo<3.1.0>hexane-1-methanol 
• 87649-53-4 (S)-3-[(1R,3aS,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ⁶-benzo[c]thiophen-5-ol 
• 86834-12-0 3-[(1R,3aS,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ⁶-benzo[c]thiophen-5-ol 

Downstream Products

• 67-97-0 vitamin D₃ 
• 50-00-0 formaldehyd 
• 62743-71-9 (5E)-10-Oxo-19-norcholecalciferol 
• 118746-80-8 8α-Hydroxy-9,10-seco-4,6,10(19)-cholestatrien-3-one 
• 67-97-0 (5E)-cholecalciferol 
• 41294-56-8 1α-hydroxycholecalciferol 
• 87649-55-6 tert-Butyl-{(S)-3-[2-[(1R,3aS)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-4-methylene-cyclohexyloxy}-dimethyl-silane 
• 86307-24-6 (1S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[2-[(1R,3aS)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-2-methylene-cyclohexanol 
• 86307-24-6 (1S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[2-[(1R,3aS)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-2-methylene-cyclohexanol 
• 71726-02-8 (S)-3-[(R)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ⁶-benzo[c]thiophen-5-ol 

Relevant academic research and scientific papers

SYNTHESIS OF CHOLESTEROL AND VITAMIN D3 FROM PHYTOSTEROLS

The present invention discloses novel method for synthesizing vegan cholesterol and vitamin D3 from inexpensive crude phytosterol.

Stereoselective Palladium-Catalyzed Approach to Vitamin D3 Derivatives in Protic Medium

We describe an efficient convergent synthesis of vitamin D3 metabolites and analogues. The synthetic strategy relies on a tandem Pd-catalyzed A-ring closure and Suzuki–Miyaura coupling to the CD-side chain component to set directly the vitamin D triene system under protic conditions. This strategy enables rapid access to vitamin D3 and 3-epi-vitamin D3 metabolites and analogues modified at the side chain for biological evaluation and structural and metabolic studies.

Probing the structural requirements for vitamin D3 inhibition of the hedgehog signaling pathway

A structure-activity relationship study to elucidate the structural basis for hedgehog (Hh) signaling inhibition by vitamin D3 (VD3) was performed. Functional and non-functional regions of VD3 and VD2 were obtained through straightforward synthetic means

Continuous-flow synthesis of vitamin D3

A highly efficient, two-stage, continuous-flow synthesis of vitamin D 3 from provitamin D3 was achieved. The developed method afforded the desired product in high yield (HPLC-UV: 60%, isolated: 32%) and required neither intermediate purification nor high-dilution conditions. The Royal Society of Chemistry 2010.

A new synthetic route to 1,25-dihydroxy-vitamin D3

A synthesis of 1,25-dihydroxy-vitamin D3 using a new acetylenic Ring-A precursor is described. Ring-A synthons 4a or 4b can be prepared in homochiral form by a diastereoselective diazoester cyclization.

Biomimetic oxidation of vitamin D by iron-sulfur model cluster and dioxygen system

Oxidation of vitamin D3 with a combination of iron-sulfur protein model cluster, (n-Bu4N)2[Fe4S4(SPh)4], and molecular oxygen produced (5E)-10-oxo-10-norvitamin D3 and 8α-hydroxy-9,10-seco-4,6,10(19)-cholestatrien-3-one, a new type of vitamin D metabolites, mimicking biological oxidation.

A General Method for the Synthesis of 3,5-Cyclovitamin D3 and Derivatives. A Stereoselective Synthesis of Vitamin D3

A stereoselective synthesis of vitamin D3 (1) was achieved via 3,5-cyclovitamin D3 (33) which was synthesized from the chiral aldehyde (3) and the vinyl bromide (27) derived from Grundmann's ketone (25). (+/-)-(Z)-5-(2-Cyclohexylidene-ethylidene)-4-methylenecyclohexane-r-1, t-3-diol (24) as a model compound of 1α-hydroxyvitamin D3 was also stereoselectively synthesized via the solvolysis of (+/-)-α-cyclohexylidenemethyl-3β-methoxymethoxy-2-methylenebicyclohexane-1-methanol (21) which was prepared from the aldehyde (12) and the organostannane (16).

Provitamin D and Vitamin D Isomerizations in the Mass Spectrometer. Translational Energy Release and Collision-induced Dissociation Studies

Collision-induced dissociation mass-analysed ion kinetic energy spectrometry and translational energy release studies have established that provitamin D3 (7-dehydrocholesterol), provitamin D2 (ergostreol), vitamin D3 and vitamin D2 isomerizations in the mass spectrometer occur at the fragment ion level leading to + ions of identical structure.It was found that the reaction, +. -> +., plays a central role in these isomerizations.