(3E)-3-[(2Z)-2-[1-[(E)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol

Base Information

• Chemical Name: (3E)-3-[(2Z)-2-[1-[(E)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol
• CAS No.: 50-14-6
• Molecular Formula: C28H44O
• Molecular Weight: 396.657
• Hs Code.: 29362900
• European Community (EC) Number: 200-014-9
• UN Number: 2811
• Wikipedia: Ergocalciferol
• Mol file: 50-14-6.mol

Synonyms:50-14-6

Chemical Property of (3E)-3-[(2Z)-2-[1-[(E)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol

Chemical Property:

• Appearance/Colour: odorless white crystals
• Vapor Pressure: 7 x l0-7 Pa (20 °C), est.)
• Melting Point: 114-118 °C(lit.)
• Refractive Index: 1.53
• Boiling Point: 504.2 °C at 760 mmHg
• PKA: 14.74±0.20(Predicted)
• Flash Point: 218.2 °C
• PSA: 20.23000
• Density: 0.97 g/cm³
• LogP: 7.64100
• Storage Temp.: 2-8°C
• Solubility.: H2O: 200 mg/mL, clear to hazy
• Water Solubility.: Soluble in ethanol, water, methanol, dimethylformamide, and dimethyl sulfoxide.
• XLogP3: 7.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 396.339216023
• Heavy Atom Count: 29
• Complexity: 678
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Vitamin D2-d3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, T+, T
• Hazard Codes: Xn,T+,T,F
• Statements: 22-48/25-26-24/25-40-23/24/25-48/22-23-11-20
• Safety Statements: 28-36/37-45-28A-36-26-36/37/39-22-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Vitamins and Derivatives
• Canonical SMILES: CC(C)C(C)C=CC(C)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C
• Isomeric SMILES: CC(C)C(C)/C=C/C(C)C1CCC\2C1(CCC/C2=C/C=C/3\CC(CCC3=C)O)C
• Recent EU Clinical Trials: Vitamin D supplementation for prevention of placenta mediated pregnancy complications.
• General Description: Vitamin D2 (ergocalciferol) is a secosteroid essential for calcium homeostasis and bone health. The trimethylsilyl ether derivative of Vitamin D2 was synthesized to enhance the stability of antirachitic preparations, demonstrating comparable biological activity to native Vitamin D2 in maintaining calcium and phosphorus metabolism. The etherified form exhibited superior storage stability, likely due to the protective role of the trimethylsilyl group against oxidative degradation, suggesting its potential for improving the shelf-life and economic viability of Vitamin D2 formulations.

Technology Process of (3E)-3-[(2Z)-2-[1-[(E)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol

There total 39 articles about (3E)-3-[(2Z)-2-[1-[(E)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol 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: 91.0%

(3S,5Z,7E)-3-(3,5-dinitro-benzoyloxy)-9,10-seco-ergosta-5,7,10(19),22t-tetraene (4712-11-2) → Calciferol (50-14-6)

Guidance literature:

With sodium hydroxide; In ethanol; at 20 ℃; for 0.75h; Inert atmosphere;

DOI:10.15227/orgsyn.076.0275

Reference yield: 23.0%

Ergosterol (57-87-4) → Calciferol (50-14-6)

Guidance literature:

Ergosterol; In 1,4-dioxane; Irradiation;

at 100 ℃;

DOI:10.1039/c2ob25511a

Reference yield:

C28H44O → Calciferol (50-14-6)

Guidance literature:

at 70 ℃; for 5h; Temperature; Inert atmosphere;

upstream raw materials:

diethyl ether

Ergosterol

lumisterol

tachysterol

Downstream raw materials:

O-(4-iodo-3-nitro-benzoyloxy)-ergocalciferol

(3S)-3-oleoyloxy-9.10-seco-ergostatetraene-(5t.7c.10⁽¹⁹⁾.22t)

N-((3S,5Z,7E)-9,10-seco-ergosta-5,7,10⁽¹⁹⁾,22t-tetraen-3-yloxycarbonyl)-L-glutamic acid

suprasterol₂-I

Refernces

Synthesis and biological activity of the trimethylsilyl ether of vitamin D₂

10.1007/BF00764628

The study focuses on the synthesis and biological activity of the trimethylsilyl ether of Vitamin D2, a compound of interest due to its potential to increase the stability of antirachitic preparations. The researchers synthesized Vitamin D2 trimethylsilyl ether (I) using a reaction involving hexamethyldisilazane and trimethylsilyl chloride, and then assessed its biological activity through various tests including calcium and phosphorus levels in blood, alkaline phosphatase activity, and the presence of a specific calcium-binding protein in the duodenal mucosa of Leghorn chicks. The results showed that the biological activity of the etherified Vitamin D2 was comparable to the non-etherified form, with some differences attributed to molecular mass and equimolar amounts. The study also examined the stability of the preparation over a six-month storage period, finding that the etherified form demonstrated greater stability, which was hypothesized to be due to the protective effects of the trimethylsilyl group against oxidation and degradation. The findings suggest that the use of silylated derivatives could reduce the loss of Vitamin D2 during storage, thereby increasing its economic value.