Cholecalciferol (undefined stereochemistry)

Base Information

• Chemical Name: Cholecalciferol (undefined stereochemistry)
• CAS No.: 22350-41-0
• Molecular Formula: C₂₇H₄₄O
• Molecular Weight: 384.646
• European Community (EC) Number: 838-947-4
• DSSTox Substance ID: DTXSID00859070
• Wikidata: Q32039085
• Mol file: 22350-41-0.mol

Synonyms:5,6-trans-Vitamin D3;9,10-secocholesta-5,7,10-trien-3-ol;DTXSID00859070;Vitamin D3;Colecalciferol;Calciol;22350-41-0;BCP34143;CID 66577030;cholecalciferol (undefined stereochemistry);FT-0675839;Q32039085;3965-99-9

Chemical Property of Cholecalciferol (undefined stereochemistry)

Chemical Property:

• Vapor Pressure: 6.16E-12mmHg at 25°C
• Refractive Index: 1.523
• Boiling Point: 496.4°Cat760mmHg
• PKA: 14.74±0.20(Predicted)
• Flash Point: 214.3°C
• PSA: 20.23000
• Density: 0.96g/cm³
• LogP: 7.61900
• XLogP3: 7.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 384.339216023
• Heavy Atom Count: 28
• Complexity: 610

Purity/Quality:

>98% ^*data from raw suppliers

5,6-trans-Vitamin D3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C
• Uses: 5,6-trans-Vitamin D3 is the major photoisomer of Vitamin D3 analog, as an impurity.

Technology Process of Cholecalciferol (undefined stereochemistry)

There total 50 articles about Cholecalciferol (undefined stereochemistry) 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: 90.0%

(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 (71726-02-8,71726-03-9,73272-02-3,73272-03-4,73809-08-2,73837-60-2,86834-12-0,87649-53-4) → (5E)-cholecalciferol (67-97-0,7489-19-2,22350-41-0,57651-82-8,57651-83-9,98744-46-8,98818-17-8)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; Heating;

DOI:10.1021/jo00359a061

Reference yield: 79.0%

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 (86834-12-0) → 5,6-trans-vitamin D3 (67-97-0,7489-19-2,57651-82-8,57651-83-9,98744-46-8,98818-17-8,22350-41-0)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; for 0.5h; Heating;

DOI:10.1016/S0040-4020(01)91875-7

Reference yield: 79.0%

(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 (87649-53-4) → 5,6-trans-vitamin D3 (67-97-0,7489-19-2,57651-82-8,57651-83-9,98744-46-8,98818-17-8,22350-41-0)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; for 0.333333h; Heating;

DOI:10.1016/S0040-4020(01)91875-7

upstream raw materials:

7-dehydrocholesterol

(5E)-10-Oxo-19-norcholecalciferol

Methylenetriphenylphosphorane

vitamin D₃

Downstream raw materials:

(5E)-cholecalciferol

1α-hydroxycholecalciferol

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

(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

Refernces

• 1、 Pelc. "". . p. 193,195, 198, 199, 200. Retrieved 1977.
• 2、 Deberardinis, Albert M.,Banerjee, Upasana,Miller, Michele,Lemieux, Steven,Hadden. "Probing the structural requirements for vitamin D3 inhibition of the hedgehog signaling pathway". scheme or table. p. 4859 - 4863. Retrieved 2012/08/13.
• 3、 Wilson, Stephen R.,Venkatesan,Augelli-Szafran,Yasmin. "A new synthetic route to 1,25-dihydroxy-vitamin D3". . p. 2339 - 2342. Retrieved 2007/10/02.