1alpha,25-Dihydroxyvitamin D3

Base Information

• Chemical Name: 1alpha,25-Dihydroxyvitamin D3
• CAS No.: 32222-06-3
• Molecular Formula: C27H44O3
• Molecular Weight: 416.645
• Hs Code.: 29061900
• Mol file: 32222-06-3.mol

Synonyms:Toptriol;Dihydroxyvitamin D3;DN 101;1.alpha.,25-dihydroxycholecalciferol;9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol, (1.alpha.,3.beta.,5Z,7E)-;GMRQFYUYWCNGIN-CLVAPQHMSA-N;1.alpha.,25-Dihydroxyvitamin D3;AKOS025401842;Cholecalciferol, 1.alpha.,25-dihydroxy-;(3.beta.,5Z,7E)-9,10-Secocholesta-5,7,10-triene-1,3,25-triol;(5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-1.alpha.,3.beta.,25-triol

Chemical Property of 1alpha,25-Dihydroxyvitamin D3

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 119-121 °C
• Refractive Index: 1.547
• Boiling Point: 565 °C at 760 mmHg
• PKA: 14.43±0.40(Predicted)
• Flash Point: 238.4 °C
• PSA: 60.69000
• Density: 1.06 g/cm³
• LogP: 5.70470
• Storage Temp.: 2-8°C
• Solubility.: Do you have solubility information on this product that you woul
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 416.32904526
• Heavy Atom Count: 30
• Complexity: 688

Purity/Quality:

99% ^*data from raw suppliers

Calcitriol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,Xn
• Hazard Codes: T+,Xn,F
• Statements: 26/27/28-63-36/37/38-20/21/22-11
• Safety Statements: 36/37/39-45-36-26-16-7

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCCC(C)(C)O)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C
• Isomeric SMILES: CC(CCCC(C)(C)O)C1CCC\2C1(CCC/C2=C\C=C\3/CC(CC(C3=C)O)O)C
• Description: Calcitriol is the active form of vitamin D and is also a kind of hormones in the body. It plays an important role in the regulation of calcium and phosphorus concentration. It can increase the blood calcium level by increasing the intestinal absorption of calcium and can also increase the release of the bone calcium release for increasing the blood calcium levels. This study was first conducted and reported by Michael F. Holick in 1971. The basic principle of action model of calcitriol in many cases is through binding with the vitamin D receptor (the VDR), e.g., the ligand-receptor complex forming between calcitriol and its receptor in the intestinal epithelial cells cytoplasm can be transferred to the nucleus for being as the transcriptional factor in promoting the expression of calcium-binding protein. The increased level of calcium-binding proteins can help the cell to actively transport of more calcium ions, thereby increasing the calcium absorption level. Calcium absorption while maintaining electrical neutrality also requires transporting anions, mainly the absorption of inorganic phosphate ions, so calcitriol also promote the absorption of phosphorus. Clinically, this drug can be used in the treatment of hypocalcemia, hypoparathyroidism (adult), osteomalacia, rickets (infants), chronic kidney disease, renal osteodystrophy, osteoporosis, as well as the prevention of glucocorticoid induced osteoporosis. Calcitriol-dimensional molecular structure The above information is edited by the lookchem of Dai Xiongfeng. Calcitriol is synthesized from 7-dehydro cholesterol in humans via a non-enzymatic photochemical reaction with 290-310 nm UV light in the skin. Hydroxylation of the resulting cholecalciferol in the liver produces 25-hydroxy vitamin D3, the principal circulating form of vitamin D. A second, tightly regulated hydroxylation in the kidney produces calcitriol. Plasma calcitriol levels range from 10-70 pg/ml and are influenced by numerous dietary and hormonal factors. The main physiologic effects of calcitriol are to increase the absorption of calcium at the level of the intestinal epithelium, and to increase the mineralization of bone via the direct stimulation of osteoblasts.
• Uses: The biologically active form of vitamin D3. Calcium regulator; vitamin (antirachitic); antihyperparathyroid; antineoplastic; antipsoriatic Calcitriol (1α,25-dihydroxy Vitamin D3) is synthesized from 7-dehydrocholesterol in humans via a non-enzymatic photochemical reaction with 290-310 nm UV light in the skin. Hydroxylation of the resulting cholecalciferol in the liver produces 25-hydroxy Vitamin D3, the principal circulating form of Vitamin D. A second, tightly regulated hydroxylation in the kidney produces calcitriol. Plasma calcitriol levels range from 10-70 pg/ml and are influenced by numerous dietary and hormonal factors. The main physiologic effects of calcitriol are to increase the absorption of calcium at the level of the intestinal epithelium, and to increase the mineralization of bone via the direct stimulation of osteoblasts.[Cayman Chemical] Calcium regulator, anti-psoriatic Vitamin medicines; it can be used for treating the renal bone malnutrition of patients with chronic renal failure
• Therapeutic Function: Calcium regulator
• Clinical Use: Vitamin D analogue: Promotes intestinal calcium absorption Suppresses PTH production and release
• Drug interactions: Potentially hazardous interactions with other drugs Antiepileptics: the effects of vitamin D may be reduced in patients taking barbiturates or anticonvulsants. Diuretics: increased risk of hypercalcaemia with thiazides. Sevelamer: absorption may be impaired by sevelamer

Technology Process of 1alpha,25-Dihydroxyvitamin D3

There total 255 articles about 1alpha,25-Dihydroxyvitamin 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: 100.0%

C30H52O3Si → calcitriol (32222-06-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 10h; Inert atmosphere;

DOI:10.1039/c2ob25511a

Reference yield: 95.0%

C45H86O3Si3 → 2-methylene-19-nor-(20S)-1α,25-dihydroxyvitamin D3 + 1α,25-dihydroxy-2-methylene-19-nor-vitamin D3 + calcitriol (32222-06-3)

Guidance literature:

With AG 50W-X₄ resin; In methanol; benzene; at 20 ℃; for 19h;

Reference yield: 95.0%

(1R,3aS,7aR)-1-((R)-5-Methoxymethoxy-1,5-dimethyl-hexyl)-7a-methyl-4-[2-[(3S,5R)-2-methylene-3,5-bis-triisopropylsilanyloxy-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-octahydro-indene (873567-12-5) → calcitriol (32222-06-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/ol052489c

upstream raw materials:

(1R,3aR,7aR)-1-{(1R)-1,5-dimethyl-5-[(trimethylsilyl)oxy]hexyl}-7a-methyloctahydro-4H-inden-4-one

[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

methyllithium

1α-Hydroxy-25-oxo-27-norvitamin D₃

Downstream raw materials:

(3R,5S)-5-((R)-2-((1R,3αS,7αR,E)-4-((Z)-2-((3S,5R)-3,5-dihydroxy-2-methylenecyclohexylidene)ethylidene)-7α-methyloctahydro-1H-inden-1-yl)propyl)-3-hydroxy-3-methyldihydrofuran-2(3H)-one

24,25,26,27-tetranor-1,23-(OH)2D₃

1α,25-dihydroxy-24-oxo-vitamin D3

(1alpha,24R,25)-trihydroxy-Vitamin D₃

Refernces

• 1、 López-Pérez, Borja,Maestro, Miguel A.,Mouri?o, Antonio. "Total synthesis of 1α,25-dihydroxyvitamin D3 (calcitriol) through a Si-assisted allylic substitution". . p. 8144 - 8147. Retrieved 2017.
• 2、 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 2013/12/04.