(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:

97%~103% ^*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.
• Description: Ergocalciferol, also under the name vitamin D2, is a type of vitamin D found in plants and yeast. It has no antirachitic activity. It helps the body to absorb calcium and phosphorus. It is used as a dietary supplement. It is used in the treatment of hypoparathyroidism (a condition in which not enough parathyroid hormone can be produced by the body), refractory rickets (softening and weakening of bones that does not respond to treatment, it is also known as vitamin D resistant rickets), and familial hypophosphatemia (rickets or osteomalacia caused by an inherited condition with a decreased ability to break down vitamin D in the body). Ergocalciferol is also used as a rodenticide. Vitamin D aids in the absorption of calcium and has central roles in bone formation and maintenance, hypertension, cancer and immunity. Vitamin D may be obtained from many dietary sources, including eggs and fish, and is synthesized in the skin by the conversion of 7-dehydrocholesterol to vitamin D3 by ultraviolet light. Vitamin D2 is produced in fungi, including yeast, and invertebrates from ergosterol in response to ultraviolet radiation. In vertebrates as well as host organisms, vitamin D2 is metabolized first to 25-hydroxyvitamin D2 and subsequently to the active 1,25-dihydroxyvitamin D2. Differences in the metabolism and action of vitamin D2 vs. vitamin D3 in mammals is a current topic of research interest.
• Uses: It can be applied to biochemical studies; its clinical drug belongs to a lipid-soluble vitamin which can promote the intestinal absorption of calcium and phosphorus which plays a role of facilitating the calcification of bone. It is clinically used for prevention and treatment of rickets in children and adult osteomalacia. Vitamin D2 can maintain the normal metabolism of calcium and phosphorus and can also promote the body's absorption of calcium and phosphorus. Upon its deficiency, the children are easy to get rickets. China ruled that it can be applied for strengthening margarine with the usage amount being 125~156 μg/kg; its usage amount in fortified dairy is 63~125μg/kg; the usage amount in strengthening infant and children food used is 50~100μg/kg; the usage amount in strengthening milk or milk beverage is 10~40μg/kg; the maximal allowable usage amount in the strengthening solid drinks and ice cream is 10~20μg/kg. It is mainly applied to the prevention and treatment of rickets, osteomalacia, and infant tetany psychosis. The synthetic form of vitamin D. Prepared from ergosterol by UV irradiation in a suitable solvent. Commercial solutions are usually made with propylene glycol or sesame oil. Antirachitic antirachitic vitamin; LD50 (rat) 56 mg/kg po Rodenticide. Vitamin d2 is fat-soluble, and is stable unless oxidized. It is necessary for growth and maintenance of teeth and bones and the normal utilization of calcium and phosphorus; it is used medicinally in the treatment of rickets and as a dietary supplement. Its sources include fish liver and vitamin d-fortified milk. Vitamin D2 is formed by photochemical cleavage of ergosterin, which is a side-product of many fermentation processes. Microorganisms usually contain up to 3 percent of ergosterin.
• Production method: Dissolve the ergosterol dissolved in ethanol and go through ring-opening under UV illumination; the reaction was further concentrated under reduced pressure, frozen, filtered, and filtered of liquid nitrogen, and concentrated under reduced pressure to dryness to obtain the crude oil of vitamin D2 with distillation to obtain the refined products. Vitamin D2 is naturally presented in the liver, egg yolk and milk; the production method of the industry starts with extracting the ergocalciferol from vegetable oil or yeast extract in the body. Further dissolve it in chloroform or cyclohexane, and then convert it to the vitamin D2 through ultraviolet radiation on the quartz glass flask. Ergosterol ethanol solution is subject to ultraviolet radiation with the 9’, 10’ bond breakage to obtain the vitamin D2 crude product; the later one further has esterification with 3, 5-nitrobenzoyl chloride and undergoes alkaline hydrolysis to get the purified product.

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

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

Refernces

• 1、 Sumi. "". . . Retrieved 1936.
• 2、 -. "Preparation method of vitamin D2". Paragraph 0089-0091; 0103-0108; 0120-0125; 0137-0141; 0152. . Retrieved 2021/05/12.
• 3、 Fuse, Shinichiro,Mifune, Yuto,Tanabe, Nobutake,Takahashi, Takashi. "Continuous-flow synthesis of activated vitamin D3 and its analogues". experimental part. p. 5205 - 5211. Retrieved 2012/08/08.