Tacalcitol

Base Information

• Chemical Name: Tacalcitol
• CAS No.: 57333-96-7
• Deprecated CAS: 131801-95-1
• Molecular Formula: C27H44O3
• Molecular Weight: 416.645
• European Community (EC) Number: 692-683-2
• UNII: C2W72OJ5ZU
• DSSTox Substance ID: DTXSID90905111
• Wikipedia: Tacalcitol
• Wikidata: Q155682
• NCI Thesaurus Code: C87292
• Pharos Ligand ID: MW6LKMHF7NPF
• Metabolomics Workbench ID: 35805
• ChEMBL ID: CHEMBL2105611
• Mol file: 57333-96-7.mol

Synonyms:1 alpha,24-dihydroxycholecalciferol;1 alpha,24-dihydroxyvitamin D3;1 alpha,24-dihydroxyvitamin D3, (1alpha,3beta,5Z,7E,24R)-isomer;1 alpha,24-dihydroxyvitamin D3, (1alpha,3beta,5Z,7E,24S)-isomer;1,24-dihydroxycholecalciferol;1,24-dihydroxyvitamin D3;Curatoderm;PRI-2191;Tacalcitol

Chemical Property of Tacalcitol

Chemical Property:

• Vapor Pressure: 4.05E-15mmHg at 25°C
• Refractive Index: 1.545
• 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: 5.56060
• Storage Temp.: Store at -20°C
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 416.32904526
• Heavy Atom Count: 30
• Complexity: 676

Purity/Quality:

98%,99%, ^*data from raw suppliers

Tacalcitol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N,T+
• Hazard Codes: N,T+

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(CCC(C)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C)O
• Isomeric SMILES: C[C@H](CC[C@H](C(C)C)O)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](C[C@@H](C3=C)O)O)C
• Recent ClinicalTrials: Efficacy and Safety of Calcipotriol Plus Hydrocortisone Ointment Compared With Tacalcitol Ointment in Patients With Psoriasis on the Face and Skin Folds
• Recent EU Clinical Trials: Calcipotriol Plus Hydrocortisone Ointment Compared with Tacalcitol Ointment in Patients with Psoriasis Vulgaris on the Face and on the Intertriginous Areas.
• Recent NIPH Clinical Trials: None
• Description: Tacalcitol, the second vitamin D analog developed as a topical antipsoriatic, was introduced for keratosis, psoriasis, ichthyosis, pityriasis rubra pilaris and palmoplantar pustulosis and keratoderma. It shows improvement in appearance of skin lesions for psoriasis patients without significant side effects. In patients with psoriasis vulgaris, it effectively inhibits keratinocyte growth. Some in vitro studies have shown that tacalcitol inhibits interleukin-1-α-induced granulocyte macrophage colony-stimulating-factor mRNA expression of the human dermal microvascular endothelial cells, which may be involved in mediation of angioproliferation in skin inflammation.

Technology Process of Tacalcitol

There total 76 articles about Tacalcitol 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: 98.0%

((1R,3S,Z)-5-((E)-2-((1R,7aR)-7a-methyl-1((2R,5R)-6-methyl-5-(triethylsilyloxy)heptan-2-yl)dihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diyl)bis(oxy)bis(tert-butyldimethylsilane) → tacalcitol (57333-96-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; Darkness;

Reference yield: 76.0%

(1R,3S)-5-[2-[(1R,3aS,7aR)-1-((1R,4R)-4-Methoxymethoxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexane-1,3-diol → tacalcitol (57333-96-7)

Guidance literature:

With hydrogen fluoride; In water; acetonitrile; at 20 ℃; for 24h;

DOI:10.1016/j.tetlet.2017.07.103

Reference yield: 75.0%

C41H74O4Si2 → tacalcitol (57333-96-7)

Guidance literature:

C₄₁H₇₄O₄Si₂; With potassium carbonate; In methanol; at 20 ℃; for 5h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h; Reflux;

upstream raw materials:

1α,3β,24(R)-trihydroxycholesta-5,7-diene

(S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol

<1R-<1β(R*),3aα,4β,7aβ>>-octahydro-4-hydroxy-β,7a-dimethyl-1H-indene-1-propanenitrile

Refernces

• 1、 -. "Process for Preparing Tacalcitol and Intermediate Therefor". . . Retrieved 2018/12/12.
• 2、 Martínez, Andrea,Santalla, Hugo,Garrido, Fátima,Gómez, Generosa,Fall, Yagamare. "Modified Julia olefination and α aminoxylation reactions mediated convergent synthesis of 1α, 24 (R)-dihydroxyvitamin D3 (tacalcitol)". supporting information. p. 3568 - 3570. Retrieved 2017/10/06.