511-28-4

Basic information

• Product Name: VITAMIN D3
• Synonyms: RACUMIN D;OLEOVITAMIN D3;VITAMIN D;ANTI-RACHITIC VITAMIN;CALCIOL;CHOLECALCIFEROLUM;COLECALCIFEROL;ACTIVATED 7-DEHYDROCHOLESTEROL
• CAS NO: 511-28-4
• Molecular Formula: C₂₈H₄₆O
• Molecular Weight: 384.64
• EINECS: 200-673-2
• Product Categories: Steroids;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 511-28-4.mol

Chemical Properties

• Melting Point: 83-86 °C(lit.)
• Boiling Point: 504.9 °C at 760 mmHg
• Flash Point: 219.2 °C
• Appearance: /
• Density: 0.96
• Storage Temp.: 2-8°C
• PKA: 14.74±0.20(Predicted)
• CAS DataBase Reference: VITAMIN D3(CAS DataBase Reference)
• NIST Chemistry Reference: VITAMIN D3(511-28-4)
• EPA Substance Registry System: VITAMIN D3(511-28-4)

Safety Data

• Hazard Codes: T+
• Statements: 24/25-26-48/25
• Safety Statements: 28-36/37
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 2
• RTECS: VS2900000
• F: 8-10-23
• Hazardous Substances Data: 511-28-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
VITAMIN D3 is used as an active analogue for various health-related applications, including the treatment and prevention of rickets, osteoporosis, and other bone disorders. It helps in maintaining the balance of calcium and phosphorus in the body, which is essential for proper bone formation and mineralization.
Used in Nutritional Supplements:
VITAMIN D3 is used as a dietary supplement to ensure adequate levels of this essential nutrient, especially for individuals with limited sun exposure or those at risk of deficiency. It supports overall health by promoting bone health, immune function, and muscle strength.
Used in Cosmetics Industry:
VITAMIN D3 is used as an ingredient in skincare products for its anti-aging and skin health benefits. It has been shown to promote cell turnover, improve skin texture, and reduce the appearance of fine lines and wrinkles.
Used in Animal Health:
VITAMIN D3 is used in the animal health industry as a supplement in livestock feed to support bone health, immune function, and overall well-being in animals. It is particularly important for young animals and those with limited access to sunlight.
Used in Research:
VITAMIN D3 is used in scientific research to study its role in various physiological processes, such as cell differentiation, proliferation, and apoptosis. It is also used to investigate the potential therapeutic applications of VITAMIN D3 in conditions like cancer, autoimmune diseases, and cardiovascular diseases.

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.

Synthetic route

Benzoic acid (S)-4-methylene-3-[2-oxo-eth-(Z)-ylidene]-cyclohexyl ester (71805-86-2) + (1R,3aR,4S,7aR)-4-benzenesulfonyl-7a-methyl-1-<(1R,4S)-1,4,5-trimethyl-hexyl>-octahydroindene (71830-70-1) → 2,2-dihydroergocalciferol (511-28-4)

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

C48H60O6S → 2,2-dihydroergocalciferol (511-28-4)

Conditions	Yield
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 → 2,2-dihydroergocalciferol (511-28-4) + 5-trans-Vitamin D(4) + (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-(E)-ylidene]-cyclohexanol

Conditions	Yield
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) → 2,2-dihydroergocalciferol (511-28-4) + tachysterol4

Conditions	Yield
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) → 2,2-dihydroergocalciferol (511-28-4)

Conditions	Yield
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) → 2,2-dihydroergocalciferol (511-28-4)

Conditions	Yield
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) → 2,2-dihydroergocalciferol (511-28-4)

Conditions	Yield
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) → 2,2-dihydroergocalciferol (511-28-4)

Conditions	Yield
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 → 2,2-dihydroergocalciferol (511-28-4)

Conditions	Yield
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 → 2,2-dihydroergocalciferol (511-28-4)

Conditions	Yield
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) → 2,2-dihydroergocalciferol (511-28-4)

Conditions	Yield
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) → 2,2-dihydroergocalciferol (511-28-4)

Conditions	Yield
With potassium nitrate In tetrahydrofuran; nitrogen; argon

2,2-dihydroergocalciferol (511-28-4) → C40H74O2Si2

Conditions

Yield

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) → C28H46O2

Conditions

Yield

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) → C34H60O3SSi

Conditions	Yield
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) → C34H60OSi

Conditions	Yield
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) → C34H60O2Si

Conditions	Yield
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) → C40H74O2Si2

Conditions	Yield
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) + tert-butyldimethylsilyl chloride (18162-48-6) → 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	Yield
With 1H-imidazole In dichloromethane at 0 - 30℃;

Upstream product

• 71805-86-2 Benzoic acid (S)-4-methylene-3-[2-oxo-eth-(Z)-ylidene]-cyclohexyl ester 
• 71830-70-1 (1R,3aR,4S,7aR)-4-benzenesulfonyl-7a-methyl-1-<(1R,4S)-1,4,5-trimethyl-hexyl>-octahydroindene 
• 20304-51-2 (24S)-ergosta-5,7-diene-3β-ol 
• 516-79-0 provitamin D₄ 
• 516-79-0 provitamin D₄ 
• 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 
• 71805-76-0 (1R,3aR,4R,5R,7aR)-7a-Methyl-4-phenylsulfanyl-1-((1R,4S)-1,4,5-trimethyl-hexyl)-octahydro-inden-5-ol 
• 66251-15-8 Benzoic acid (S)-3-[2-hydroxy-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester 

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