previtamin D3

Base Information

• Chemical Name: previtamin D3
• CAS No.: 1173-13-3
• Molecular Formula: C27H44 O
• Molecular Weight: 384.646
• Hs Code.: 29362900
• European Community (EC) Number: 214-634-2
• UNII: HDA46400N5
• DSSTox Substance ID: DTXSID90862573
• Metabolomics Workbench ID: 35771
• Wikidata: Q139299
• Wikipedia: Previtamin_D3
• Mol file: 1173-13-3.mol

Synonyms:(3beta,6Z)-9,10-secocholesta-5(10),6,8-trien-3-ol;(3S,6E)-9,10-Secocholesta-5(10),6,8-trien-3-ol;(3S,6Z)-9,10-secocholesta-5(10),6,8-trien-3-ol;1,25-dihydroxy-3-epi-19-nor-previtamin D3;14-epi-19-nortachysterol;precalciferol;precholecalciferol;previtamin D(3);previtamin D(3), (3alpha,6Z)-isomer;previtamin D(3), (3beta,6E)-isomer;previtamin D3;tachysterol 3;tachysterol(3);tachysterol3

Chemical Property of previtamin D3

Chemical Property:

• Boiling Point: 496°Cat760mmHg
• PKA: 14.84±0.60(Predicted)
• Flash Point: 214.1°C
• PSA: 20.23000
• Density: 1.017g/cm³
• LogP: 7.61900
• XLogP3: 7.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 7
• Exact Mass: 384.339216023
• Heavy Atom Count: 28
• Complexity: 622

Purity/Quality:

98%,99%, ^*data from raw suppliers

PrevitaminD3(>80%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(CC(CC1)O)C=CC2=CCCC3(C2CCC3C(C)CCCC(C)C)C
• Isomeric SMILES: CC1=C(C[C@H](CC1)O)/C=C\C2=CCC[C@]3([C@H]2CC[C@@H]3[C@H](C)CCCC(C)C)C
• Uses: Vitamin D3 (V676045) isomer. Vitamin D3 mediates intestinal calcium absorbtion, bone calcium metabolism and many other processes. During exposure to sunlight 7-dehydrocholesterol in converted to pre-vitamin D3, which undergoes a rapid transformation within the plasma membrane to vitamin D3.

Technology Process of previtamin D3

There total 48 articles about previtamin D3 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: 44.0%

(-)-9,10-secocholesta-5(10),8-dien-6-yn-ol → previtamin D3 (1173-13-3)

Guidance literature:

With quinoline; hydrogen; Lindlar's catalyst; In hexane; ethyl acetate; for 0.75h;

DOI:10.1021/jo00055a011

Reference yield:

previtamin D3 (1173-13-3) → 7-dehydrocholesterol (434-16-2) + Lumisterol3 (5226-01-7) + tachysterol3 (1173-13-3,17592-07-3,24945-46-8,57651-22-6)

Guidance literature:

Quantum yield; Irradiation; 302.5 and 254 nm;

DOI:10.1016/S0040-4039(01)82052-9

Reference yield:

C35H60O → previtamin D3 (1173-13-3) + tachysterol3 (17592-07-3)

Guidance literature:

With 2,6-di-tert-butyl-4-methyl-phenol; In tert-butyl methyl ether; at 20 ℃; for 5.5h; Irradiation;

DOI:10.1021/acs.joc.9b03482

upstream raw materials:

diethyl ether

7-dehydrocholesterol

vitamin D₃

tachysterol₃

Downstream raw materials:

O-(3.5-dinitro-benzoyl)-cholecalciferol

(3bR,5aR,6R,8aR,10S)-6-((R)-1,5-Dimethyl-hexyl)-10-((S)-5-hydroxy-2-methyl-cyclohex-1-enyl)-5a-methyl-2-phenyl-4,5,5a,6,7,8,8a,10-octahydro-3bH-2,3a,10a-triaza-dicyclopenta[a,f]naphthalene-1,3-dione

7-dehydrocholesterol

Lumisterol₃

Refernces

• 1、 Nowakowska, Maria,Foyle, Victor P.,Guillet, James E.. "Studies of the antenna effect in polymer molecules. 24. Solar photosynthesis of previtamin D3 in aqueous solutions of poly(sodium styrenesulfonate-co-2-vinylnaphthalene)". . p. 5975 - 5981. Retrieved 1993.
• 2、 Fuss, Werner,Hoefer, Thomas,Hering, Peter,Kompa, Karl L.,Lochbrunner, Stefan,et al.. "Ring Opening in the Dehydrocholesterol-Previtamin D Dystem Studied by Ultrafast Spectroscopy". . p. 921 - 927. Retrieved 1996.
• 3、 Havinga. "-". . p. 1181,1185. Retrieved 1973.
• 4、 Malatesta,Willis,Hackett. "Laser photochemical production of vitamin D". . p. 6781 - 6783. Retrieved 1981.
• 5、 Zmijewski, Michal A.,Li, Wei,Zjawiony, Jordan K.,Sweatman, Trevor W.,Chen, Jianjun,Miller, Duane D.,Slominski, Andrzej T.. "Photo-conversion of two epimers (20R and 20S) of pregna-5,7-diene-3β, 17α, 20-triol and their bioactivity in melanoma cells". scheme or table. p. 218 - 228. Retrieved 2009/04/14.