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Vitamin D2(CAS No. 50-14-6)

Vitamin D2 C28H44O (cas 50-14-6) Molecular Structure

50-14-6 Structure

Identification and Related Records

Vitamin D2
【CAS Registry number】
Ergosterol, activated
Oleovitamin D2
Secoergosta-5,7,10(19),22-tetraen-3-ol, (3beta,5Z,7E,22E)-
Vitamin D
9,10-Secoergosta-5,7,10(19),22-tetraen-3-ol, (3beta,5Z,7E,22E)-
Divit urto
Calciferon 2
Davitamon D
【Molecular Formula】
C28H44O (Products with the same molecular formula)
【Molecular Weight】
【Canonical SMILES】
【Isomers smiles】
【MOL File】

Chemical and Physical Properties

odorless white crystals
0.97 g/cm3
【Melting Point】
【Boiling Point】
504.2 oC at 760 mmHg
【Refractive Index】
【Flash Point】
218.2 oC
82 o (C=3, IN ACETONE 25 oC)
H2O: 200 mg/mL, clear to hazy
H2O: 200 mg/mL, clear to hazy
Prisms from acetone
White crystals
Colorless crystals
【Storage temp】
【Spectral properties】
Specific optical rotation: +82.6 @ 25 deg C/D (c= 3 in acetone); +102.5 @ 20 deg C/D (alcohol); specific optical rotation: +52 @ 20 deg C/D (chloroform); UV max absorption (hexane): 264.5 nm (e= 458.9 +/- 7.5, 1%, 1 cm)
IR: 14471 (Sadtler Research Laboratories Prism Collection)
UV: 5-899 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
NMR: 364 (Varian Associates NMR Spectra Catalogue)
MASS: 33088 (NIST/EPA/MSDC Mass Spectral Database, 1990 version)
【Computed Properties】
Molecular Weight:396.64836 [g/mol]
Molecular Formula:C28H44O
H-Bond Donor:1
H-Bond Acceptor:1
Rotatable Bond Count:5
Exact Mass:396.339216
MonoIsotopic Mass:396.339216
Topological Polar Surface Area:20.2
Heavy Atom Count:29
Formal Charge:0
Isotope Atom Count:0
Defined Atom Stereocenter Count:6
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:3
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Donor Count:1
Feature 3D Hydrophobe Count:3
Feature 3D Ring Count:3
Effective Rotor Count:7
Conformer Sampling RMSD:0.8
CID Conformer Count:20

Safety and Handling

【Hazard Codes】
【Risk Statements】
【Safety Statements 】

Poison by ingestion, intraperitoneal, intravenous, and intramuscular routes. An experimental teratogen. Human systemic effects by ingestion: anorexia, nausea or vomiting, and weight loss. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes:?Xn,T+,T
Risk Statements: 22-48/25-26-24/25-40-23/24/25?
R22: Harmful if swallowed.?
R48: Danger of serious damage to health by prolonged exposure.?
R25: Toxic if swallowed.?
R26: Very toxic by inhalation.?
R40: Limited evidence of a carcinogenic effect.?
R23/24/25: Toxic by inhalation, in contact with skin and if swallowed.
Safety Statements: 28-36/37-45-28A-36-26-36/37/39-22?
S28: After contact with skin, wash immediately with plenty of soap-suds.?
S36/37: Wear suitable protective clothing and gloves.?
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S36: Wear suitable protective clothing.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.?
S22: Do not breathe dust.
RIDADR: UN 2811 6.1/PG 2
WGK Germany: 3
RTECS: KE1050000
F: 1-8-10
HazardClass: 6.1(a)
PackingGroup of Ergocalciferol (CAS NO.50-14-6): II

【PackingGroup 】
UN 2811
Ergocalciferol capsules usually consist of the drug in an edible oil solution encapsulated with gelatin. Commercially available ergocalciferol solution is a clear solution of the drug in an edible vegetable oil or in propylene glycol. Ergocalciferol injection is a sterile solution of the drug in sesame oil.
Ergocalciferol is also commercially available in combination with other vitamins and minerals, analgesic-antipyretics, amino acids, infant formulas, laxatives, and protein supplements.
Parenteral: Injection (for IM use only): 12.5 mg (500,000 units) per mL, Calciferol (in oil), (Schwarz)
Ergocalciferol (calciferol; Drisdol) is pure vitamin D2. ... Available in capsules or tablets that contain 1.25 mg (50,000 USP units) each. An oral solution (8,000 units/mL) of the vitamin in propylene glycol is also available. An injection in oil (500,000 units/mL) is available for im administration. ... Dihydrotachysterol (DHT; hytakerol) is the pure crystalline compound obtained by reduction of vitamin D2 ... Available as tablets (0.125 to 0.4 mg), capsules (0.125 mg), an oral soln (0.2 mg/mL) & a soln in oil (0.2 mg/mL).
Grades: USP, FCC as vitamin D2.
... Four main types of vitamin D preparations: (1) fish liver oils ... (2) multivitamin ... (3) Preparations containing vitamin D & calcium salts ... (4) preparation containing vitamin D activity alone.
Commercial solutions are usually made with propylene glycol or sesame oil.
【Exposure Standards and Regulations】
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
Vitamin D2 used as a dietary supplement in food for human consumption is generally recognized as safe when used in accordance with good manufacturing practice.
Vitamin D2 used as a nutrient and/or dietary supplement in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.

? Ergocalciferol (CAS NO.50-14-6), its Synonyms are Viosterol ; Vitamin D2 ; (+)-Vitamin D2 ; (3-beta,5Z,7E,22E)-9,10-Secoergosta-5,7,10,(19),22-tetraen-3-ol ; 9,10-Seco(5Z,7E,22E)-5,7,10(19),22-ergostatetraen-3-ol ; 9,10-Secoergosta-5,7,10(19),22-tetraen-3-beta-ol ; Activated ergosterol ; Buco-D ; Calciferol ; Calciferolum ; Davitamon D ; Davitin ; De-rat concentrate ; Cyclohexanol, 4-methylene-3-((2E)-2-((1R,3aS,7aR)-octahydro-7a-methyl-1-((1R,2E,4R)-1,4,5-trimethyl-2-hexen-1-yl)-4H-inden-4-ylidene)ethylidene)-, (1S,3Z)- . It is odorless white crystals.

【Octanol/Water Partition Coefficient】
log Kow = 10.44 /Estimated/

EPA Extremely Hazardous Substances List.

【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

/Is/ the synthetic form of vitamin D. Prepared from ergosterol by UV irradiation in a suitable solvent. ... The best wavelengths for production of vitamin D2 seem to be from 275 to 300 nm ... Prepn by electron bombardment of ergosterol using longer waves ... .
Usually obtained from yeast which synthesizes it from simple sugars such as glucose.
U.S. Imports

(1984) 9.16X10+7 g /Vitamin D-2 and D-3, synthetic/
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

Biomedical Effects and Toxicity

【Pharmacological Action】
- Organic substances that are required in small amounts for maintenance and growth, but which cannot be manufactured by the human body.
【Therapeutic Uses】
MEDICATION (VET): ... Recommended for prophylaxis of milk fever in cows. ... Prevent atrophic rhinitis in pigs. ... Aid fracture healing in cats and dogs.
MEDICATION (VET): To be effective ... supplementation with Ca & PO4. ... Fish meals & irradiated yeast may be used as supplemental ... source. ... Diets are routinely supplemented ... 1400-1600 IU/kg. Therapy for rickets ... Level 10-20 times daily requirement, alternate days for 1 wk. /Vitamin D/
In adults and children with nutritional rickets or osteomalacia and normal GI absorption, oral administration of ... ergocalciferol daily results in normal serum calcium and phosphate concentrations in about 10 days, radiographic evidence of healing of bone within 2-4 wk, and complete healing in about 6 months. ... Diet should be corrected and, after healing has occurred, supplemental doses of ergocalciferol may be discontinued in patients with normal GI absorption. In adults with severe malabsorption and vitamin D deficiency, /daily/ dosages ... have been given to correct osteomalacia. In children with malabsorption, oral ergocalciferol dosages ... have been recommended. In vitamin D-deficient infants with tetany and rickets, calcium should be administered orally or iv to control tetany. Vitamin D deficiency is then treated orally with /a daily dose/ of ergocalciferol ... until the bones have healed, ... .
In adults with Fanconi syndrome, oral ergocalciferol .. have been given along with treatment of acidosis. In children with Fanconi syndrome oral ergocalciferol ... have been used.
In patients with rickets or osteomalacia secondary to anticonvulsant therapy, oral ergocalciferol dosages ... may be required. Some clinicians recommend prophylactic administration of ... ergocalciferol ... in patients receiving long-term anticonvulsant therapy .
/Exptl therapy:/ In patients with osteoporosis oral ergocalciferol ... have been used with calcium and fluoride supplements.
For the management of hypoparathyroidism or pseudohypoparathyroidism in adults, oral ergocalciferol ... may be required with calcium supplements and/or im or iv parathyroid hormone. Children with hypoparathyroidism or pseudohypoparathyroidism are usually treated with ... oral ergocalciferol daily and calcium supplements. Prolonged administration of ergocalciferol dosages greater than 2.5 mg daily in adults or children is likely to result in toxicity. Dosage should be gradually decreased as serum calcium concentrations approach normal.
... Ergocalciferol /is/ used for treatment of chronic and latent form of postoperative tetany and idiopathic tetany. /NOT included in US product labeling/
Ergocalciferol is indicated for prevention and treatment of vitamin D deficiency states. Vitamin D deficiency may occur as a result of inadequate nutrition, intestinal malabsorption, or lack of exposure to sunlight, but does not occur in healthy individuals receiving an adequate balanced diet and exposure to sunlight. Vitamin D therapy, alone, as treatment for osteoporosis is not generally recommended; however, vitamin D supplements ... may be used as part of the prevention and treatment of osteoporosis in patients with an inadequate vitamin D and/or calcium intake. For prophylaxis of vitamin D deficiency, dietary improvement, rather than supplementation, is advisable. For treatment of vitamin D deficiency, supplementation is preferred. /Included in US product labeling/
Topical application of ergocalciferol to hairless mouse dorsal skin, and exposure to solar-simulating ultraviolet (UV) radiation at a dose of 10.8 J/cm(2) (UVA) were performed for 15 weeks, five times a week on weekdays. At the end of the final irradiation, histological and analytical studies were performed. Topical application of ergocalcifero significantly prevented wrinkle formation and abnormal accumulation of extracellular matrix components. In addition, ergocalcifero suppressed excessive secretion of IL-6 induced by UV irradiation in cultured human normal keratinocytes, in a dose-dependent manner. Ergocalcifero promoted keratinocytes differentiation in the epidermis and showed diverse physiological effects, the same as the active form of VD(3). The results suggested that the suppression of skin photodamage involved the promotion of keratinocytes differentiation and suppression of IL-6 secretion induced by exposure to UV. Topical application of ergocalciferol may become an effective means to suppress solar UV-induced human skin damage. [Mitani H et al; Photodermatol Photoimmunol Photomed 20 (5): 215-23 (2004)]
【Biomedical Effects and Toxicity】
Both vitamin D2 & vitamin D3 are absorbed from the small intestine, although vitamin D3 may be absorbed more efficiently. The exact portion of the gut that is most effective in vitamin D absorption reflects the vehicle in which the vitamin is dissolved. Most of the vitamin appears first within chylomicrons in lymph.
The presence of bile is required for absorption of ergocalciferol and the extent of GI absorption may be decreased in patients with hepatic, biliary, or GI disease (e.g., Crohn's disease, Whipple's disease, sprue).
A longitudinal, randomized, double blind, placebo controlled study was conducted for 6 months to monitor ultraviolet B light exposure in human milk-fed infants both with and without supplemental vitamin D2, and to measure longitudinally the bone mineral content, growth, and serum concentrations of calcium, phosphorus, 25-hydroxyvitamin D3, 25-hydroxyvitamin D2, 1,25-dihydroxyvitamin D, and parathyroid hormone. Sequential sampling was performed of 46 human milk-fed white infants; 24 received 400 IU/day of vitamin D2, and 22 received placebo. An additional 12 patients were followed who received standard infant formula. 83% of patients completed a full 6 months of the study. Ultraviolet B light exposure and measurements of growth did not differ between groups. At 6 months, the human milk groups did not differ significantly in bone mineral content or serum concentrations of parathyroid hormone or 1,25-dihydroxyvitamin D, although total 25-hydroxyvitamin D values were significantly less in the unsupplemented human milk group (23.53 + or - 9.94 vs 36.96 + or - 11.86 ng/ml; pPubMed Abstract
A comparison was made of the ability of ergocalciferol and cholecalciferol to elevate plasma concentrations of vitamin D and 25-hydroxyvitamin D in cats. Cholecalciferol, given as an oral bolus in oil, resulted in a rapid elevation of plasma concentration of cholecalciferol followed by a rapid decline. In contrast, 25-hydroxyvitamin D concentration in plasma increased until day 3 after administration and remained elevated for a further 5 days. When 337 microg of both cholecalciferol and ergocalciferol in oil were given as an oral bolus to 10 cats, the peak plasma concentrations of cholecalciferol and ergocalciferol occurred at 8 or 12 h after administration. Peak concentrations of cholecalciferol were over twice those of ergocalciferol (570 +/- 80 vs. 264 +/- 42 nmol/l). The area under the curve 0-169 h for cholecalciferol was also more than twice that for ergocalciferol. When ergocalciferol and cholecalciferol were administered in a parenteral oil-based emulsion, higher concentrations of 25-hydroxyvitamin D3 than 25-hydroxyvitamin D2 were maintained in plasma. When both vitamins were included in the diet in the nutritional range, plasma concentrations of 25-hydroxyvitamin D2 were 0.68 of those of 25-hydroxyvitamin D3. Discrimination against ergocalciferol by cats appears to result from differences in affinity of the binding protein for the metabolites of the two forms of vitamin D. These results indicate that cats discriminate against ergocalciferol, and use it with an efficiency of 0.7 of that of cholecalciferol to maintain plasma 25-hydroxyvitamin D concentration. [Morris JG; J Anim Physiol Anim Nutr (Berl) 86 (7-8): 229-38 (2002)] PubMed Abstract
Osteoporosis diminishes the quality of life in adults with cystic fibrosis (CF). Vitamin D deficiency resulting from malabsorption may be a factor in the etiology of low bone mineral density (BMD) in patients with CF. OBJECTIVE: Absorption of oral ergocalciferol (vitamin D2) and the consequent response of 25-hydroxyvitamin D in 10 adults with CF and exocrine pancreatic insufficiency was compared with that of 10 healthy control subjects. DESIGN: In this pharmacokinetic study, CF patients and control subjects were pair-matched on age, sex, and race. Each subject consumed 2500 microg oral vitamin D2 with a meal. The CF group also took pancreatic enzymes that provided > or = 80000 U lipase. Blood samples were obtained at baseline and at 5, 10, 24, 30, and 36 h after vitamin D2 consumption to measure serum vitamin D2 and 25-hydroxyvitamin D concentrations. RESULTS: Vitamin D2 concentrations in all subjects were near zero at baseline. CF patients absorbed less than one-half the amount of oral vitamin D2 that was absorbed by control subjects (P PubMed Abstract

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