Calderol

Base Information

• Chemical Name: Calderol
• CAS No.: 19356-17-3
• Molecular Formula: C27H44O2
• Molecular Weight: 400.645
• Hs Code.: 29362900
• European Community (EC) Number: 242-990-9,621-370-5
• UNII: P6YZ13C99Q
• Wikipedia: Calcifediol
• Wikidata: Q27286305
• NCI Thesaurus Code: C65278
• RXCUI: 1889
• ChEMBL ID: CHEMBL3544909
• Mol file: 19356-17-3.mol

Synonyms:25 Hydroxycholecalciferol;25 Hydroxycholecalciferol Monohydrate;25 Hydroxyvitamin D 3;25 Hydroxyvitamin D3;25-Hydroxycholecalciferol;25-Hydroxycholecalciferol Monohydrate;25-Hydroxyvitamin D 3;25-Hydroxyvitamin D3;Anhydrous, Calcifediol;Calcidiol;Calcifediol;Calcifediol Anhydrous;Calcifediol, (3 alpha,5Z,7E)-Isomer;Calcifediol, (3 beta,5E,7E)-Isomer;Calderol;Dedrogyl;Hidroferol;Monohydrate, 25-Hydroxycholecalciferol

Chemical Property of Calderol

Chemical Property:

• Vapor Pressure: 2.07E-13mmHg at 25°C
• Melting Point: 74-76oC
• Boiling Point: 529.2 °C at 760 mmHg
• PKA: 14.74±0.20(Predicted)
• Flash Point: 221.4 °C
• PSA: 40.46000
• Density: 1.01 g/cm³
• LogP: 6.73390
• Storage Temp.: −20°C
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 418.34469533
• Heavy Atom Count: 30
• Complexity: 655

Purity/Quality:

99% ^*data from raw suppliers

25-Hydroxyvitamin D3 ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCCC(C)(C)O)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C.O
• 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.O
• Recent ClinicalTrials: Vitamin D Supplementation on in Major Orthopedic Surgery
• Recent EU Clinical Trials: Multicenter, double-blind, randomized clinical trial to evaluate the efficacy of calcifediol soft capsules versus placebo in reducing hospital admissions in patients with a positive diagnostic test for SARS-CoV-2.
• Description: Calcifediol (synonym 25-Hydroxyvitamin D3) is a vitamin D analog and the major metabolite of vitamin D3 (Cholecalciferol) in the liver. Its main function is the regulation of calcium and phosphorus, which is necessary for strong bones. It is used to treat patients with serious kidney diseases to decrease the parathyroid hormone (PTH) level. It is used to treat rickets and osteomalacia, both in azotemic and non-azotemic patient. Calcifediol is sold under RAYALDEE? to treat secondary hyperparathyroidism associated with vitamin D insufficiency in stage 3-4 chronic kidney disease.
• Uses: 25-Hydroxyvitamin D3-23,24,25,26,27-13C5?can be used as a stable isotope internal standard for data interpretation in specific biological samples by mass spectrometry. A metabolite of Vitamin D. The principal circulating form of vitamin D3, formed in the liver by hydroxylation at C-25. Calcium regulator. This product may be used as an analytical standard.
• Therapeutic Function: Calcium regulator

Technology Process of Calderol

There total 71 articles about Calderol 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: 100.0%

vitamin D3 (67-97-0) → calcidiol (19356-17-3)

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: 83.6%

9,10-secocholesta-5,7,10(19)-triene-3β,25-diol → calcidiol (19356-17-3)

Guidance literature:

With anthracene; triethylamine; In ethanol; at 20 - 30 ℃; for 0.333333h; Irradiation;

Reference yield: 82.0%

3β,25-dihydroxy-9,10-secocholesta-5(E),7(E),10(19)-triene (1233749-00-2) → calcidiol (19356-17-3)

Guidance literature:

With anthracene; triethylamine; In benzene; for 1h; Irradiation;

DOI:10.1021/jo00375a013

upstream raw materials:

methyl magnesium iodide

(R)-methyl 5-((1R,3aS,7aR,E)-4-((Z)-2-((S)-5-((tert-butyldimethylsilyl)oxy)-2-methylenecyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)hexanoate

3β,25-dihydroxy-9,10-secocholesta-5(E),7(E),10(19)-triene

methylmagnesium bromide

Downstream raw materials:

25-hydroxyvitamin D₃ 3-hemiglutarate

25-hydroxy previtamin D₃

25-hydroxyvitamin D₃ pertrimethylsilyl ether

(R)-6-{(1R,3aS)-4-[2-[(S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol

Refernces

• 1、 Fujii, Tadashi,Fujii, Yoshikazu,Machida, Kazuhiro,Ochiai, Atsushi,Ito, Masashi. "Efficient biotransformations using Escherichia coli with tolC acrAB mutations expressing cytochrome P450 genes". . p. 805 - 810. Retrieved 2009.
• 2、 Schmitz, Lisa Marie,Kinner, Alina,Althoff, Kirsten,Rosenthal, Katrin,Lütz, Stephan. "Investigation of Vitamin D2 and Vitamin D3 Hydroxylation by Kutzneria albida". . p. 2266 - 2274. Retrieved 2021.
• 3、 Yasutake, Yoshiaki,Nishioka, Taiki,Imoto, Noriko,Tamura, Tomohiro. "A single mutation at the ferredoxin binding site of P450 Vdh enables efficient biocatalytic production of 25-hydroxyvitamin D3". . p. 2284 - 2291. Retrieved 2013.
• 4、 Yasutake, Yoshiaki,Fujii, Yoshikazu,Nishioka, Taiki,Cheon, Woo-Kwang,Arisawa, Akira,Tamura, Tomohiro. "Structural evidence for enhancement of sequential vitamin D3 hydroxylation activities by directed evolution of cytochrome P450 vitamin D 3 hydroxylase". . p. 31193 - 31201. Retrieved 2010.
• 5、 -. "IMPROVED, COST EFFECTIVE PROCESS FOR SYNTHESIS OF VITAMIN D3 AND ITS ANALOGUE CALCIFEDIOL FROM ERGOSTEROL". Page/Page column 49. . Retrieved 2021/01/29.