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511-28-4

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511-28-4 Usage

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.

Chemical Properties

Pale Yellow Oil

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.

Check Digit Verification of cas no

The CAS Registry Mumber 511-28-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,1 and 1 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 511-28:
(5*5)+(4*1)+(3*1)+(2*2)+(1*8)=44
44 % 10 = 4
So 511-28-4 is a valid CAS Registry Number.

511-28-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name vitamin D4

1.2 Other means of identification

Product number -
Other names (3S,5Z,7E)-9,10-Secoergosta-5,7,10-trien-3-ol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:511-28-4 SDS

511-28-4Synthetic route

Benzoic acid (S)-4-methylene-3-[2-oxo-eth-(Z)-ylidene]-cyclohexyl ester
71805-86-2

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
71830-70-1

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

2,2-dihydroergocalciferol
511-28-4

2,2-dihydroergocalciferol

Conditions
ConditionsYield
(i) ClSiMe3, (ii) Li-Hg; Multistep reaction;
C48H60O6S

C48H60O6S

2,2-dihydroergocalciferol
511-28-4

2,2-dihydroergocalciferol

Conditions
ConditionsYield
With sodium amalgam
tert-Butyl-dimethyl-{(S)-4-methylene-3-[2-[(1R,3aS,7aR)-7a-methyl-1-((1R,4S)-1,4,5-trimethyl-hexyl)-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-cyclohexyloxy}-silane

tert-Butyl-dimethyl-{(S)-4-methylene-3-[2-[(1R,3aS,7aR)-7a-methyl-1-((1R,4S)-1,4,5-trimethyl-hexyl)-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-cyclohexyloxy}-silane

A

2,2-dihydroergocalciferol
511-28-4

2,2-dihydroergocalciferol

B

5-trans-Vitamin D(4)

5-trans-Vitamin D(4)

C

(S)-4-Methylene-3-[2-[(1R,3aS,7aR)-7a-methyl-1-((1R,4S)-1,4,5-trimethyl-hexyl)-octahydro-inden-(4Z)-ylidene]-eth-(Z)-ylidene]-cyclohexanol

(S)-4-Methylene-3-[2-[(1R,3aS,7aR)-7a-methyl-1-((1R,4S)-1,4,5-trimethyl-hexyl)-octahydro-inden-(4Z)-ylidene]-eth-(Z)-ylidene]-cyclohexanol

D

(S)-4-Methylene-3-[2-[(1R,3aS,7aR)-7a-methyl-1-((1R,4S)-1,4,5-trimethyl-hexyl)-octahydro-inden-(4Z)-ylidene]-eth-(E)-ylidene]-cyclohexanol

(S)-4-Methylene-3-[2-[(1R,3aS,7aR)-7a-methyl-1-((1R,4S)-1,4,5-trimethyl-hexyl)-octahydro-inden-(4Z)-ylidene]-eth-(E)-ylidene]-cyclohexanol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 1h; Yield given; Yields of byproduct given;
(24S)-ergosta-5,7-diene-3β-ol
20304-51-2, 38521-88-9, 516-79-0

(24S)-ergosta-5,7-diene-3β-ol

A

2,2-dihydroergocalciferol
511-28-4

2,2-dihydroergocalciferol

B

tachysterol4

tachysterol4

Conditions
ConditionsYield
With diethyl ether Irradiation.UV-Licht (Magnesium-Funken); Reinigung ueber das O-<3.5-Dinitro-benzoyl>-Derivat;
Benzoic acid (S)-3-[2-hydroxy-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester
66251-15-8

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

2,2-dihydroergocalciferol
511-28-4

2,2-dihydroergocalciferol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: MnO2
2: (i) ClSiMe3, (ii) Li-Hg
View Scheme
Multi-step reaction with 3 steps
1: MnO2
2: (i) nBuLi, (ii) /BRN= 471389/, Py
3: Na-Hg
View Scheme
Benzoic acid (S)-4-methylene-3-[2-oxo-eth-(Z)-ylidene]-cyclohexyl ester
71805-86-2

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

2,2-dihydroergocalciferol
511-28-4

2,2-dihydroergocalciferol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (i) nBuLi, (ii) /BRN= 471389/, Py
2: Na-Hg
View Scheme
(1R,3aR,4R,5R,7aR)-7a-Methyl-4-phenylsulfanyl-1-((1R,4S)-1,4,5-trimethyl-hexyl)-octahydro-inden-5-ol
71805-76-0

(1R,3aR,4R,5R,7aR)-7a-Methyl-4-phenylsulfanyl-1-((1R,4S)-1,4,5-trimethyl-hexyl)-octahydro-inden-5-ol

2,2-dihydroergocalciferol
511-28-4

2,2-dihydroergocalciferol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: Py
2: m-ClC6H4CO3H
3: KOtBu
4: H2 / Pd-C
5: (i) ClSiMe3, (ii) Li-Hg
View Scheme
Multi-step reaction with 6 steps
1: Py
2: m-ClC6H4CO3H
3: KOtBu
4: H2 / Pd-C
5: (i) nBuLi, (ii) /BRN= 471389/, Py
6: Na-Hg
View Scheme
(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

(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

2,2-dihydroergocalciferol
511-28-4

2,2-dihydroergocalciferol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2 / Pd-C
2: (i) ClSiMe3, (ii) Li-Hg
View Scheme
Multi-step reaction with 3 steps
1: H2 / Pd-C
2: (i) nBuLi, (ii) /BRN= 471389/, Py
3: Na-Hg
View Scheme
Benzoic acid (1R,3aR,4R,5R,7aR)-7a-methyl-4-phenylsulfanyl-1-((1R,4S)-1,4,5-trimethyl-hexyl)-octahydro-inden-5-yl ester

Benzoic acid (1R,3aR,4R,5R,7aR)-7a-methyl-4-phenylsulfanyl-1-((1R,4S)-1,4,5-trimethyl-hexyl)-octahydro-inden-5-yl ester

2,2-dihydroergocalciferol
511-28-4

2,2-dihydroergocalciferol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: m-ClC6H4CO3H
2: KOtBu
3: H2 / Pd-C
4: (i) ClSiMe3, (ii) Li-Hg
View Scheme
Multi-step reaction with 5 steps
1: m-ClC6H4CO3H
2: KOtBu
3: H2 / Pd-C
4: (i) nBuLi, (ii) /BRN= 471389/, Py
5: Na-Hg
View Scheme
Benzoic acid (1R,3aR,4R,5R,7aR)-4-benzenesulfonyl-7a-methyl-1-((1R,4S)-1,4,5-trimethyl-hexyl)-octahydro-inden-5-yl ester

Benzoic acid (1R,3aR,4R,5R,7aR)-4-benzenesulfonyl-7a-methyl-1-((1R,4S)-1,4,5-trimethyl-hexyl)-octahydro-inden-5-yl ester

2,2-dihydroergocalciferol
511-28-4

2,2-dihydroergocalciferol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: KOtBu
2: H2 / Pd-C
3: (i) ClSiMe3, (ii) Li-Hg
View Scheme
Multi-step reaction with 4 steps
1: KOtBu
2: H2 / Pd-C
3: (i) nBuLi, (ii) /BRN= 471389/, Py
4: Na-Hg
View Scheme
(1R,3aR,4S,7aR)-4-benzenesulfonyl-7a-methyl-1-<(1R,4S)-1,4,5-trimethyl-hexyl>-octahydroindene
71830-70-1

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

2,2-dihydroergocalciferol
511-28-4

2,2-dihydroergocalciferol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (i) nBuLi, (ii) /BRN= 471389/, Py
2: Na-Hg
View Scheme
(24S)-ergosta-5,7-diene-3β-ol
20304-51-2, 38521-88-9, 516-79-0

(24S)-ergosta-5,7-diene-3β-ol

2,2-dihydroergocalciferol
511-28-4

2,2-dihydroergocalciferol

Conditions
ConditionsYield
With potassium nitrate In tetrahydrofuran; nitrogen; argon
2,2-dihydroergocalciferol
511-28-4

2,2-dihydroergocalciferol

C40H74O2Si2

C40H74O2Si2

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 1H-imidazole / dichloromethane / 0 - 30 °C
2: sulfur dioxide / dichloromethane / -20 °C / Darkness
3: sodium hydrogencarbonate / ethanol / Inert atmosphere; Reflux; Darkness
4: 4-methyl-morpholine; selenium(IV) oxide / dichloromethane; acetonitrile / Reflux
5: 1H-imidazole / dichloromethane / 2 h / 0 - 20 °C
6: anthracene; triethylamine / toluene / 20 °C / Inert atmosphere; UV-irradiation
View Scheme
2,2-dihydroergocalciferol
511-28-4

2,2-dihydroergocalciferol

C28H46O2

C28H46O2

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 1H-imidazole / dichloromethane / 0 - 30 °C
2: sulfur dioxide / dichloromethane / -20 °C / Darkness
3: sodium hydrogencarbonate / ethanol / Inert atmosphere; Reflux; Darkness
4: 4-methyl-morpholine; selenium(IV) oxide / dichloromethane; acetonitrile / Reflux
5: 1H-imidazole / dichloromethane / 2 h / 0 - 20 °C
6: anthracene; triethylamine / toluene / 20 °C / Inert atmosphere; UV-irradiation
7: tetrabutyl ammonium fluoride / tetrahydrofuran / 60 °C / Inert atmosphere; Darkness; Reflux
View Scheme
2,2-dihydroergocalciferol
511-28-4

2,2-dihydroergocalciferol

C34H60O3SSi

C34H60O3SSi

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1H-imidazole / dichloromethane / 0 - 30 °C
2: sulfur dioxide / dichloromethane / -20 °C / Darkness
View Scheme
2,2-dihydroergocalciferol
511-28-4

2,2-dihydroergocalciferol

C34H60OSi

C34H60OSi

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1H-imidazole / dichloromethane / 0 - 30 °C
2: sulfur dioxide / dichloromethane / -20 °C / Darkness
3: sodium hydrogencarbonate / ethanol / Inert atmosphere; Reflux; Darkness
View Scheme
2,2-dihydroergocalciferol
511-28-4

2,2-dihydroergocalciferol

C34H60O2Si

C34H60O2Si

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1H-imidazole / dichloromethane / 0 - 30 °C
2: sulfur dioxide / dichloromethane / -20 °C / Darkness
3: sodium hydrogencarbonate / ethanol / Inert atmosphere; Reflux; Darkness
4: 4-methyl-morpholine; selenium(IV) oxide / dichloromethane; acetonitrile / Reflux
View Scheme
2,2-dihydroergocalciferol
511-28-4

2,2-dihydroergocalciferol

C40H74O2Si2

C40H74O2Si2

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1H-imidazole / dichloromethane / 0 - 30 °C
2: sulfur dioxide / dichloromethane / -20 °C / Darkness
3: sodium hydrogencarbonate / ethanol / Inert atmosphere; Reflux; Darkness
4: 4-methyl-morpholine; selenium(IV) oxide / dichloromethane; acetonitrile / Reflux
5: 1H-imidazole / dichloromethane / 2 h / 0 - 20 °C
View Scheme
2,2-dihydroergocalciferol
511-28-4

2,2-dihydroergocalciferol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

tert-Butyl-dimethyl-{(S)-4-methylene-3-[2-[(1R,3aS,7aR)-7a-methyl-1-((1R,4S)-1,4,5-trimethyl-hexyl)-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-cyclohexyloxy}-silane

tert-Butyl-dimethyl-{(S)-4-methylene-3-[2-[(1R,3aS,7aR)-7a-methyl-1-((1R,4S)-1,4,5-trimethyl-hexyl)-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-cyclohexyloxy}-silane

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 0 - 30℃;

511-28-4Downstream Products

511-28-4Relevant articles and documents

VITAMIN D DERIVATIVES AND PROCESS FOR PRODUCING THE SAME

-

, (2008/06/13)

A process for producing hydroxyvitamin D derivatives, characterized by converting a hydrogen atom or atoms at the 2-position, 24-position, 25-position and/or 26-position of a vitamin D into a hydroxyl group or groups in a solution containing a microorganism that belongs to the genus Nocardia, Streptomyces,Sphingomonas or Amycolata which has an ability to hydroxylate vitamin Ds or an enzyme produced by that microorganism, and optionally under the coexistence of a cyclodextrin; and novel vitamin D3 derivatives obtained by that process.

Methods of treating skin disorders with novel 1a-hydroxy vitamin D4 compounds and derivatives thereof

-

, (2008/06/13)

The disclosure is of methods of treating various skin disorders, including skin cancer, with compounds of novel 1α-hydroxy vitamin D4 and novel analogues, thereof, including 1,25 dihydroxy vitamin D4 and 1,24 dihydroxy vitamin D4. Novel 1α-hydroxy vitamin D4 compounds and compounds of novel analogues suitable for use in the treatment of such disorders are also disclosed herein.

1 alpha-hydroxy vitamins D7 and D4' processes for the preparation thereof and pharmaceutical compositions

-

, (2008/06/13)

Disclosed are new 1α-hydroxy vitamin D7 of formula (I) and 1α-hydroxy vitamin D4 of formula (II) which are useful as active ingredients of pharmaceutical compositions for the treatment of osteoporosis. Those new compounds are synthesized starting from (22E)-5α,8α-(4-phenyl-1,2-urazolo)-6,22-ergostadien-3β-ol 3β-tert-butyl-dimethylsilyl ether and through ten process steps.

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