24,25-Dihydroxyergocalciferol

Base Information

• Chemical Name: 24,25-Dihydroxyergocalciferol
• CAS No.: 71183-99-8
• Molecular Formula: C₂₈H₄₄O₃
• Molecular Weight: 428.656
• Mol file: 71183-99-8.mol

Synonyms:24,25-dihydroxyergocalciferol;24,25-dihydroxyvitamin D2;24,25-dihydroxyvitamin D2, (3beta,5Z,7E,22E,24S)-isomer;24,25-dihydroxyvitamin D2, (3beta,5Z,7E,22E,24xi)-isomer

Chemical Property of 24,25-Dihydroxyergocalciferol

Chemical Property:

• Vapor Pressure: 5.59E-16mmHg at 25°C
• Boiling Point: 582.2°C at 760 mmHg
• PKA: 14.53±0.29(Predicted)
• Flash Point: 244.8°C
• PSA: 60.69000
• Density: 1.06g/cm³
• LogP: 5.87080
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 428.32904526
• Heavy Atom Count: 31
• Complexity: 773

Purity/Quality:

99% ^*data from raw suppliers

24(R,S),25-DihydroxyvitaminD2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C=CC(C)(C(C)(C)O)O)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C
• Isomeric SMILES: C[C@H](/C=C/[C@](C)(C(C)(C)O)O)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@@H](CCC3=C)O)C

Technology Process of 24,25-Dihydroxyergocalciferol

There total 21 articles about 24,25-Dihydroxyergocalciferol 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:

ercalcidiol (21343-40-8) → (24R)-24,25-dihydroxyvitamin D2 (58050-55-8,71135-11-0,71183-99-8,104974-17-6)

Guidance literature:

With glucose-6-phosphate dehydrogenase; glucose-6-phosphate; bovine adrenodoxin reductase; bacterial P₄₅₀ monooxygenase CYP₁₀₉E₁; truncated bovine adrenodoxin (Adx_4-108); water; magnesium chloride; In aq. phosphate buffer; ethanol; glycerol; at 30 ℃; pH=7.4; regioselective reaction; Enzymatic reaction;

DOI:10.1016/j.bbrc.2020.01.091

Reference yield:

Calciferol (50-14-6) → ercalcidiol (21343-40-8) + (24R)-24,25-dihydroxyvitamin D2 (58050-55-8,71135-11-0,71183-99-8,104974-17-6)

Guidance literature:

With glucose-6-phosphate dehydrogenase; glucose-6-phosphate; bovine adrenodoxin reductase; bacterial P₄₅₀ monooxygenase CYP₁₀₉E₁; truncated bovine adrenodoxin (Adx_4-108); water; magnesium chloride; In aq. phosphate buffer; glycerol; at 30 ℃; pH=7.4; Reagent/catalyst; regioselective reaction; Enzymatic reaction;

DOI:10.1016/j.bbrc.2020.01.091

Reference yield:

3-hydroxy-3-methyl-2-butanone tetrahydropyranyl ether (60283-66-1) → (24R)-24,25-dihydroxyvitamin D2 (58050-55-8,71135-11-0,71183-99-8,104974-17-6)

Guidance literature:

Multi-step reaction with 5 steps

2: 60 percent

3: 70 percent / lithium aluminium hydride / tetrahydrofuran

5: 1.) irradiation, 2.) reflux, 2 h

With lithium aluminium tetrahydride; In tetrahydrofuran;

DOI:10.1248/cpb.32.3744

upstream raw materials:

(22E,24S)-3β,24,25-trihydroxyergosta-5,7,22-triene

3-hydroxy-3-methyl-2-butanone tetrahydropyranyl ether

(24R,S)-ergosta-5,7,22-triene-3β,24,25-triol

(22E)-3β-acetoxy-25-hydroxy-5α,8α-(3,5-dioxo-4-phenyl-1,2,4-triazolidino)cholesta-6,22-dien-24-one

Refernces

• 1、 Katsumi,Okano,Ono,Maegaki,Nishimura,Baba,Kobayashi,Miyata,Naito,Ninomiya. "Syntheses of 24,25-dihydroxyvitamin D2, 24,25-dihydroxy-22-dehydrovitamin D3, 25-hydroxy-24-oxo-22-dehydrovitamin D3 and 22,24,25-trihydroxyvitamin D3". . p. 970 - 979. Retrieved 2007/10/02.