Vitamin D4

Base Information

• Chemical Name: Vitamin D4
• CAS No.: 511-28-4
• Molecular Formula: C28H46O
• Molecular Weight: 398.673
• Hs Code.: 2936240000
• European Community (EC) Number: 208-127-5
• UNII: KN41X73N6C
• DSSTox Substance ID: DTXSID801026994
• Wikipedia: 22-Dihydroergocalciferol
• Wikidata: Q2706046
• Metabolomics Workbench ID: 36230
• Mol file: 511-28-4.mol

Synonyms:Vitamin D4;22,23-dihydroergocalciferol;511-28-4;24S-Methylcalciol;22,23-dihydroercalciol;22,23-Dihydrovitamin D2;UNII-KN41X73N6C;KN41X73N6C;VITAMIND3;22-Dihydroergocalciferol;EINECS 208-127-5;(1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(2R,5S)-5,6-dimethylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol;9,10-Secoergosta-5(Z),7(E),10(19)-trien-3beta-ol;(3S)-9,10-seco-5Z,7E,10(19)-ergostatrien-3-ol;9,10-Secocholesta-5,7,10(9)-trien-3-ol, 24-methyl-;(5Z,7E)-(3S)-9,10-Seco-5,7,10(19)-ergostatrien-3-ol;22:23-dihydrovitamin D2;VITAMIN D4 [MI];VITAMIN D4 (VD4);(3-beta,5Z,7E)-9,10-Secoergosta-5,7,10(19)-trien-3-ol;SCHEMBL1030053;CHEBI:33237;DIPPFEXMRDPFBK-JPWDPSJFSA-N;DTXSID801026994;LMST03030001;AKOS016009245;CS-0804;22,23-Dihydroergocalciferol [WHO-DD];ERGOCALCIFEROL, 22,23-DIHYDRO-;AC-26351;HY-75958;C18192;E85757;ERGOCALCIFEROL IMPURITY G [EP IMPURITY];22,23-Dihydroergocalciferol, >=97.0% (HPLC);Q2706046;(3S,5Z,7E)-9,10-secoergosta-5,7,10(19)-trien-3-ol;(3beta,5Z,7E)-9,10-secoergosta-5,7,10(19)-trien-3-ol;(5Z,7E)-(3S)-9,10-secoergosta-5,7,10(19)-trien-3-ol;(5Z,7E)-9,10-SECOERGOSTA-5,7,10(19)-TRIEN-3.BETA.-OL;9,10-SECOERGOSTA-5,7,10(19)-TRIEN-3-OL, (3.BETA.,5Z,7E)-;22-DIHYDROERGOCALCIFEROL(5Z,7E)-(3S)-9,10-SECO-5,7,10(19)-ERGOSTATRIEN-3-OL(24S)-METHYLCALCIOL;CYCLOHEXANOL, 4-METHYLENE-3-((2E)-2-((1R,3AS,7AR)-OCTAHYDRO-7A-METHYL-1-((1R,4S)-1,4,5-TRIMETHYLHEXYL)-4H-INDEN-4-YLIDENE)ETHYLIDENE)-, (1S,3Z)-

Chemical Property of Vitamin D4

Chemical Property:

• Melting Point: 96-98ºC
• Boiling Point: 504.9 °C at 760 mmHg
• PKA: 14.74±0.20(Predicted)
• Flash Point: 219.2 °C
• PSA: 20.23000
• Density: 0.96 g/cm³
• LogP: 7.64100
• Storage Temp.: 2-8°C
• XLogP3: 8.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 398.354866087
• Heavy Atom Count: 29
• Complexity: 639

Purity/Quality:

99% ^*data from raw suppliers

Vitamin D ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 24/25-26-48/25
• Safety Statements: 28-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C)CCC(C)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C
• Isomeric SMILES: C[C@H](CC[C@H](C)C(C)C)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](CCC3=C)O)C
• Description: Derived from cholesterol, vitamin D is biosynthesized from its prohormone cholecalciferol (D3), the product of solar ultraviolet irradiation of 7-dehydrocholesterol in the skin. In 1966, it was first recognized that vitamin D must undergo activation via two oxidative metabolic steps. The first oxidation to 25-hydroxycholecalciferol (25(OH)D3: calcifediol; Calderol) occurs in the endoplasmic reticulum of the liver and is catalyzed by vitamin D 25-hydroxylase. This activation step is not regulated by plasma calcium concentrations. The major circulating form (10–80 μg/mL) is 25(OH)D3, which also is the primary storage form of vitamin D.
• Uses: Vitamin D4 is the active analogue of Vitamin D.
• Biological Functions: Sterol-specific cytoplasmic receptor proteins (vitamin D receptor) mediate the biological action of vitamin D. The active hormone is transported from the cytoplasm to the nucleus via the vitamin D receptor, and as a result of the interaction of the hormone with target genes, a variety of proteins are produced that stimulate the transport of calcium in each of the target tissues Active vitamin D works in concert with PTH to enhance active intestinal absorption of calcium, to stimulate bone resorption, and to prohibit renal excretion of calcium. If serum calcium or 1,25-calcitriol concentrations are elevated, then vitamin D 24-hydroxylase (in renal mitochondria) is activated to oxidize 25(OH)D3 to inactive 24,25-dihydroxy-cholecalciferol and to further oxidize active vitamin D to the inactive 1,24,25-trihydroxylated derivative. Both the 1,24,25-trihydroxylated and the 24,25-dihydroxylated products have been found to suppress PT H secretion as well. The biosynthesis of vitamin D is tightly regulated based on the serum concentrations of calcium, phosphate, PTH, and active vitamin D.

Technology Process of Vitamin D4

There total 22 articles about Vitamin D4 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:

(24S)-ergosta-5,7-diene-3β-ol (20304-51-2,38521-88-9,516-79-0) → 2,2-dihydroergocalciferol (511-28-4)

Guidance literature:

With potassium nitrate; In tetrahydrofuran; nitrogen; argon;

Reference yield:

(1R,3aR,4R,5R,7aR)-7a-Methyl-4-phenylsulfanyl-1-((1R,4S)-1,4,5-trimethyl-hexyl)-octahydro-inden-5-ol (71805-76-0) → 2,2-dihydroergocalciferol (511-28-4)

Guidance literature:

Multi-step reaction with 5 steps

1: Py

2: m-ClC₆H₄CO₃H

3: KOtBu

4: H₂ / Pd-C

5: (i) ClSiMe₃, (ii) Li-Hg

With pyridine; potassium tert-butylate; hydrogen; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal;

Reference yield:

(1R,3aR,4R,7aR)-4-Benzenesulfonyl-7a-methyl-1-((1R,4S)-1,4,5-trimethyl-hexyl)-2,3,3a,4,7,7a-hexahydro-1H-indene (71805-88-4) → 2,2-dihydroergocalciferol (511-28-4)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd-C

2: (i) ClSiMe₃, (ii) Li-Hg

With hydrogen; palladium on activated charcoal;

upstream raw materials:

Benzoic acid (S)-4-methylene-3-[2-oxo-eth-(Z)-ylidene]-cyclohexyl ester

(1R,3aR,4S,7aR)-4-benzenesulfonyl-7a-methyl-1-<(1R,4S)-1,4,5-trimethyl-hexyl>-octahydroindene

(24S)-ergosta-5,7-diene-3β-ol

Benzoic acid (S)-3-[2-hydroxy-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester

Refernces

• 1、 Blakmore,Grzywacz,Kocienski,Marczak,Wicha. "On the Julia Alkenylation reaction in vitamin D synthesis. Isolation of four geometrical isomers of vitamin D4". . p. 1209 - 1217. Retrieved 2007/10/03.
• 2、 -. "Method of inhibiting the hyperproliferation of malignant cells". . . Retrieved 2008/06/13.