calcidiol 3-O-(beta-D-glucuronide)

Base Information

• Chemical Name: calcidiol 3-O-(beta-D-glucuronide)
• CAS No.: 170512-14-8
• Molecular Formula: C₃₃H₅₂O₈
• Molecular Weight: 576.771
• UNII: YN76CW017E
• Nikkaji Number: J741.406D
• Mol file: 170512-14-8.mol

Synonyms:25Ohd3-g;calcidiol 3-O-(beta-D-glucuronide);170512-14-8;25Ohd3-3-o-glucuronide;YN76CW017E;25-hydroxyvitamin D3 3-glucuronide;(2S,3S,4S,5R,6R)-6-[(1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid;calcidiol 3-glucuronide;calcidiol 3-O-glucoronide;calcidiol 3-beta-glucuronide;UNII-YN76CW017E;CHEBI:139613;25(OH)D33G;calcidiol 3-O-(beta-D-glucuronic acid);25-hydroxyvitamin D3 3-O-(beta-D-glucuronide);25-hydroxyvitamin D3 3-O-(beta-D-glucuronic acid);(1S,3Z)-3-((2E)-2-((1R,3AS,7AR)-1-((1R)-5-HYDROXY-1,5-DIMETHYLHEXYL)OCTAHYDRO-7A-METHYL-4H-INDEN-4-YLIDENE)ETHYLIDENE)-4-METHYLENECYCLOHEXYL .BETA.-D-GLUCOPYRANOSIDURONIC ACID;(1S,3Z)-3-((2E)-2-((1R,3aS,7aR)-1-((1R)-5-Hydroxy-1,5-dimethylhexyl)octahydro-7a-methyl-4H-inden-4-ylidene)ethylidene)-4-methylenecyclohexyl beta-D-glucopyranosiduronic acid;(1S,3Z)-3-[(2E)-2-{(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyloctahydro-4H-inden-4-ylidene}ethylidene]-4-methylidenecyclohexyl beta-D-glucopyranosiduronic acid;(3beta,5Z,7E)-25-Hydroxy-9,10-secocholesta-5,7,10(19)-trien-3-yl beta-D-Glucopyranosiduronic Acid;(3S,5Z,7E)-25-hydroxy-9,10-secocholesta-5,7,10(19)-trien-3-yl beta-D-glucopyranosiduronic acid;.BETA.-D-GLUCOPYRANOSIDURONIC ACID, (1S,3Z)-3-((2E)-2-((1R,3AS,7AR)-1-((1R)-5-HYDROXY-1,5-DIMETHYLHEXYL)OCTAHYDRO-7A-METHYL-4H-INDEN-4-YLIDENE)ETHYLIDENE)-4-METHYLENECYCLOHEXYL;.BETA.-D-GLUCOPYRANOSIDURONIC ACID, (3.BETA.,5Z,7E)-25-HYDROXY-9,10-SECOCHOLESTA-5,7,10(19)-TRIEN-3-YL;beta-D-Glucopyranosiduronic acid, (1S,3Z)-3-((2E)-2-((1R,3aS,7aR)-1-((1R)-5-hydroxy-1,5-dimethylhexyl)octahydro-7a-methyl-4H-inden-4-ylidene)ethylidene)-4-methylenecyclohexyl;beta-D-Glucopyranosiduronic acid, (3beta,5Z,7E)-25-hydroxy-9,10-secocholesta-5,7,10(19)-trien-3-yl

Chemical Property of calcidiol 3-O-(beta-D-glucuronide)

Chemical Property:

• Melting Point: >114oC (dec.)
• Storage Temp.: Amber Vial, -86°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 576.36621861
• Heavy Atom Count: 41
• Complexity: 1020

Purity/Quality:

25-Hydroxyvitamin D3 3-Glucuronide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(CCCC(C)(C)O)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)OC4C(C(C(C(O4)C(=O)O)O)O)O)C
• Isomeric SMILES: C[C@H](CCCC(C)(C)O)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](CCC3=C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O)O)O)C
• Uses: 25-Hydroxyvitamin D3 3-Glucuronide is an glucuronidated conjugate of 5-Hydroxyvitamin D3 (C125700), the principal circulating form of vitamin D3, formed in the liver by hydroxylation at C-25. Calcium regulator.

Technology Process of calcidiol 3-O-(beta-D-glucuronide)

There total 3 articles about calcidiol 3-O-(beta-D-glucuronide) 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: 84.6%

methyl<(5Z,7E)-(3S)-25-hydroxy-9,10-secocholesta-5,7,10(19)-trien-3-yl-2',3',4'-tri-O-acetyl-β-D-glucopyranosid>uronate → <(5Z,7E)-(3S)-25-hydroxy-9,10-secocholesta-5,7,10(19)-trien-3-yl>-β-D-glucopyranosiduronic acid (170512-14-8)

Guidance literature:

With sodium hydroxide; In methanol; dichloromethane; for 17h; Ambient temperature;

DOI:10.1248/cpb.43.1379

Reference yield:

methyl(cholesta-5,7-dien-25-ol-3β-yl-2',3',4'-tri-O-acetyl-β-D-glucopyranosid)uronate (170512-04-6) → <(5Z,7E)-(3S)-25-hydroxy-9,10-secocholesta-5,7,10(19)-trien-3-yl>-β-D-glucopyranosiduronic acid (170512-14-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Et₂O, CH₂Cl₂, 0 deg C, 23 s, irrad., 2.) hexane, THF, RT, 7 d

2: 84.6 percent / NaOH / CH₂Cl₂; methanol / 17 h / Ambient temperature

With sodium hydroxide; In methanol; dichloromethane;

DOI:10.1248/cpb.43.1379

Reference yield:

calcidiol (19356-17-3) + UDP-glucuronic acid (2616-64-0) → <(5Z,7E)-(3S)-3-hydroxy-9,10-secocholesta-5,7,10(19)-trien-25-yl>-β-D-glucopyranosiduronic acid + <(5Z,7E)-(3S)-25-hydroxy-9,10-secocholesta-5,7,10(19)-trien-3-yl>-β-D-glucopyranosiduronic acid (170512-14-8)

Guidance literature:

With fresh female Wistar rat liver microsomal fraction; In various solvent(s); at 37 ℃; for 2h; pH=7.2; Further Variations:; Reagents; Product distribution;

DOI:10.1248/bpb.20.596

upstream raw materials:

calcidiol

UDP-glucuronic acid

methyl(cholesta-5,7-dien-25-ol-3β-yl-2',3',4'-tri-O-acetyl-β-D-glucopyranosid)uronate

Refernces

• 1、 Shimada,Sugaya,Kaji,Nakatani,Mitamura,Tsutsumi. "Syntheses and enzymatic hydrolysis of 25-hydroxyvitamin D monoglucuronides". . p. 1379 - 1384. Retrieved 2007/10/02.