(1S,3E)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol

Base Information

• Chemical Name: (1S,3E)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol
• CAS No.: 21343-40-8
• Molecular Formula: C28H44O2
• Molecular Weight: 412.656
• European Community (EC) Number: 606-742-7
• Mol file: 21343-40-8.mol

Synonyms:21343-40-8

Chemical Property of (1S,3E)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol

Chemical Property:

• Vapor Pressure: 5.06E-14mmHg at 25°C
• Melting Point: 45-51°C
• Boiling Point: 542.3°C at 760 mmHg
• PKA: 14.74±0.20(Predicted)
• Flash Point: 225.9°C
• PSA: 40.46000
• Density: 1.02g/cm³
• LogP: 6.75590
• Storage Temp.: −20°C
• Solubility.: Limited solubility, soluble in DMSO or ethanol
• XLogP3: 6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 412.334130642
• Heavy Atom Count: 30
• Complexity: 725

Purity/Quality:

99% ^*data from raw suppliers

Ercalcidiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,F
• Hazard Codes: T+,F
• Statements: 24/25-26-48/25-11
• Safety Statements: 28-36/37-45-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C=CC(C)C(C)(C)O)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C
• Isomeric SMILES: C[C@H](/C=C/[C@H](C)C(C)(C)O)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C\3/C[C@H](CCC3=C)O)C
• Uses: 25-Hydroxyvitamin D2 may be used as a certified reference material (CRM) for the determination of the analyte in biological samples by chromatography techniques. A metabolite of Vitamin D2 (V676040). 25-Hydroxyvitamin D2?can be used as an analytical standard for the quantitative analysis of 25-Hydroxyvitamin D2?content in biological fluids via LC-MS/MS.

Technology Process of (1S,3E)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol

There total 35 articles about (1S,3E)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol 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%

Calciferol (50-14-6) → ercalcidiol (21343-40-8)

Guidance literature:

With dihydrogen peroxide; In aq. phosphate buffer; at 40 ℃; for 1h; pH=7; regioselective reaction; Enzymatic reaction;

DOI:10.1002/cctc.201402795

Reference yield: 76.0%

25-<(methoxymethyl)oxy>vitamin D2 tert-butyldimethylsilyl ether (100858-28-4) → ercalcidiol (21343-40-8)

Guidance literature:

With AG-50WX₄(resin); In methanol; for 16h; Ambient temperature;

DOI:10.1021/jo00358a018

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

upstream raw materials:

methyl magnesium iodide

(E)-(R)-6-{(1R,7aR)-4-[2-[(S)-5-Hydroxy-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-3-methyl-hept-4-en-2-one

(3S,10R,13R,17R)-10,13-Dimethyl-17-[(E)-(R)-1-methyl-4-(2-methyl-[1,3]dioxolan-2-yl)-pent-2-enyl]-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

(S)-4-Methyl-3-((Z)-2-{(1R,7aR)-7a-methyl-1-[(E)-(R)-1-methyl-4-(2-methyl-[1,3]dioxolan-2-yl)-pent-2-enyl]-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl}-vinyl)-cyclohex-3-enol

Downstream raw materials:

7,8-epoxy-25-hydroxyvitamin D₂

<1R<1β(R^*,E,S),3aα,7aβ>>-6-(Octahydro-7a-methyl-1H-4-oxoinden-1-yl)-2,3-dimethyl-4-hepten-2-ol

7,8,25-trihydroxyvitamin D₂

(24R)-24,25-dihydroxyvitamin D₂

Refernces

• 1、 Putkaradze, Natalia,K?nig, Lisa,Kattner, Lars,Hutter, Michael C.,Bernhardt, Rita. "Highly regio- and stereoselective hydroxylation of vitamin D2 by CYP109E1". . p. 295 - 300. Retrieved 2020/01/31.
• 2、 Babot, Esteban D.,Del R??o, Jos?? C.,Kalum, Lisbeth,Mart??nez, Angel T.,Guti??rrez, Ana. "Regioselective hydroxylation in the production of 25-hydroxyvitamin D by Coprinopsis cinerea peroxygenase". . p. 283 - 290. Retrieved 2015/02/19.