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vitamin D2

Chemical Structure

General Material Information

Preferred name vitamin D2
Trivial Name (+)-Vitamin D2
Short Description (5Z,7E,22E)-(3S)-9,10-seco-5,7,10(19),22-ergostatetraen-3-ol
Formula C28 H44 O
CAS Number 50-14-6
ECHA Number 200-014-9
FDA UNII VS041H42XC
Nikkaji Number J1.907K
Beilstein Number 1916682
MDL MFCD00166988
xLogP3-AA 7.40 (est)
Bio Activity Summary External link
NMR Predictor External link
FDA Mainterm 50-14-6 ; VITAMIN D-2
Synonyms
  • (1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan
  • (3beta,5Z,7E,22E)-9,10-secoergosta-5,7,10(19),22-tetraen-3-ol
  • (3S,5Z,7E,14xi,17alpha,22E)-9,10-secoergosta-5,7,10,22-tetraen-3-ol
  • (3S,5Z,7E,22E)-9,10-secoergosta-5,7,10,22-tetraen-3-ol
  • (3S,5Z,7E,22E)-9,10-secoergosta-5,7,10(19),22-tetraen-3-ol
  • (5E,7E,22E)-9,10-secoergosta-5,7,10,22-tetraen-3-ol
  • (5Z,7E,22E)-(3S)-9,10-seco-5,7,10(19),22-ergostatetraen-3-ol
  • (5Z,7E,22E)-(3S)-9,10-secoergosta-5,7,10(19),22-tetraen-3-ol
  • 4-methylene-3-[2-[tetrahydro-7a-methyl-1-(1,4,5-trimethyl-2-hexenyl)-4(3aH)-indanylidene]ethylidene]-cyclohexanol
  • 9,10-secoergosta-5,7,10(19),22-tetraen-3-ol, (3.beta.,5Z,7E,22E)-
  • 9,10-secoergosta-5,7,10(19),22-tetraen-3-ol, (3beta,5Z,7E,22E)-
  • 9,10-seco(5Z,7E,22E)-5,7,10(19),22-ergostatetraen-3-ol
  • calciferol
  • calciferolum
  • cycloheanol, 4-methylene-3-(2-(tetrahydro-7a-methyl-1-(1,4,5-trimethyl-2-hexenyl)-4(3aH)-indanylidene)ethylidene)-
  • 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)-
  • D- arthin
  • D- tracetten
  • ergocalciferol
  • ergocalciferolum
  • ergorone
  • ergosterol activated
  • oleovitamin D
  • oleovitamin D2
  • 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)-
  • 9,10-Secoergosta-5,7,10(19),22-tetraen-3-ol, (3β,5Z,7E,22E)-
  • Cyclohexanol, 4-methylene-3-[2-[tetrahydro-7a-methyl-1-(1,4,5-trimethyl-2-hexenyl)-4(3aH)-indanylidene]ethylidene]-
  • (1S,3Z)-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]cyclohexanol
  • D-Arthin
  • Condocaps
  • Condol
  • Crystallina
  • Davitin
  • Decaps
  • Dee-Osterol
  • Dee-Ron
  • Dee-Ronal
  • Deratol
  • Deltalin
  • Detalup
  • Diactol
  • Divit urto
  • Doral
  • Drisdol
  • Ertron
  • Fortodyl
  • Geltabs
  • Hi-Deratol
  • Infron
  • Mulsiferol
  • Mykostin
  • Ostelin
  • Metadee
  • Radiostol
  • Radsterin
  • Shock-ferol
  • Viosterol
  • Vitavel-D
  • 9,10-Secoergosta-5,7,10(19),22-tetraen-3β-ol
  • Buco-D
  • Rodine C
  • (+)-Vitamin D2
  • D-Tracetten
  • Osteil
  • De-Rat Concentrate
  • Sterogyl
  • Mina D2
  • Uvesterol D
  • Vio D
  • NSC 62792
  • Ercalciol

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Literature & References

(1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:50-14-6
Pubchem (cid):5280793
Pubchem (sid):134971005
Publications by PubMed
Extract-Filter-Shoot Liquid Chromatography with Mass Spectrometry for the Analysis of Vitamin D2 in a Powdered Supplement Capsule and Standard Reference Material 3280.
Mushrooms and Health Summit Proceedings.
Dietary vitamin D2 - a potentially underestimated contributor to vitamin D nutritional status of adults?
Statistical optimization of ultraviolet irradiate conditions for vitamin D₂ synthesis in oyster mushrooms (Pleurotus ostreatus) using response surface methodology.
Simultaneous determination of vitamins D2 and D3 by electrospray ionization LC/MS/MS in infant formula and adult nutritionals: First Action 2012.11.
Development of an analytical protocol for the estimation of vitamin D(2) in fortified toned milk.
Dynamics of sterols and fatty acids during UV-B treatment of oyster mushroom.
Stability of vitamin D in foodstuffs during cooking.
Vitamin D2-enriched button mushroom (Agaricus bisporus) improves memory in both wild type and APPswe/PS1dE9 transgenic mice.
Quadruple parallel mass spectrometry for analysis of vitamin D and triacylglycerols in a dietary supplement.
Dispersive liquid-liquid microextraction for the determination of vitamins D and K in foods by liquid chromatography with diode-array and atmospheric pressure chemical ionization-mass spectrometry detection.
Vitamin D₂ from UVB light exposed mushrooms modulates immune response to LPS in rats.
Quantification of vitamin D and 25-hydroxyvitamin D in soft tissues by liquid chromatography-tandem mass spectrometry.
Vitamin D in plants: a review of occurrence, analysis, and biosynthesis.
Safety assessment of the post-harvest treatment of button mushrooms (Agaricus bisporus) using ultraviolet light.
Method for simultaneous analysis of eight analogues of vitamin D using liquid chromatography tandem mass spectrometry.
Comprehensive profiling of carotenoids and fat-soluble vitamins in milk from different animal species by LC-DAD-MS/MS hyphenation.
A.S.P.E.N. position paper: recommendations for changes in commercially available parenteral multivitamin and multi-trace element products.
Fortified malted milk drinks containing low-dose ergocalciferol and cholecalciferol do not differ in their capacity to raise serum 25-hydroxyvitamin D concentrations in healthy men and women not exposed to UV-B.
Increase of vitamin D(2) by UV-B exposure during the growth phase of white button mushroom (Agaricus bisporus).
Impact of high-pressure processing on vitamin E (α-, γ-, and δ-tocopherol), vitamin D (cholecalciferol and ergocalciferol), and fatty acid profiles in liquid foods.
Vitamin D2 from light-exposed edible mushrooms is safe, bioavailable and effectively supports bone growth in rats.
Characterization of ergocalciferol loaded solid lipid nanoparticles.
Effects of postharvest pulsed UV light treatment of white button mushrooms (Agaricus bisporus) on vitamin D2 content and quality attributes.
Seasonal variation of provitamin D2 and vitamin D2 in perennial ryegrass (Lolium perenne L.).
Vitamin D and sterol composition of 10 types of mushrooms from retail suppliers in the United States.
Bioavailability and efficacy of vitamin D2 from UV-irradiated yeast in growing, vitamin D-deficient rats.
Evaluation of a method based on liquid chromatography-diode array detector-tandem mass spectrometry for a rapid and comprehensive characterization of the fat-soluble vitamin and carotenoid profile of selected plant foods.
Simultaneous determination of cholecalciferol (vitamin D3) and ergocalciferol (vitamin D2) in foods by selected reaction monitoring.
Meals and dephytinization affect calcium and zinc absorption in Nigerian children with rickets.
Vitamin D: a rapid review.
Vitamin D2 formation and bioavailability from Agaricus bisporus button mushrooms treated with ultraviolet irradiation.
Hypovitaminosis D in chronic kidney disease patients: prevalence and treatment.
Hypovitaminosis D is common among pulmonary tuberculosis patients in Tanzania but is not explained by the acute phase response.
Vitamin D: a rapid review.
Evaluation of ergosterol and its esters in the pileus, gill, and stipe tissues of agaric fungi and their relative changes in the comminuted fungal tissues.
Angiotensin-converting enzyme inhibitory and antioxidant activities of enzymatically synthesized phenolic and vitamin glycosides.
Vitamin D2 formation from post-harvest UV-B treatment of mushrooms (Agaricus bisporus) and retention during storage.
Effect of UV-B exposure on the concentration of vitamin D2 in sliced shiitake mushroom (Lentinus edodes) and white button mushroom (Agaricus bisporus).
Vitamin D in foods: development of the US Department of Agriculture database.
Vitamin D deficiency: a worldwide problem with health consequences.
Induction of apoptosis by vitamin D2, ergocalciferol, via reactive oxygen species generation, glutathione depletion, and caspase activation in human leukemia Cells.
Convenient analysis of vitamin D in cheese and other food matrixes by liquid chromatography/mass spectrometry.
Detection and quantification of provitamin D2 and vitamin D2 in hop (Humulus lupulus L.) by liquid chromatography-diode array detection-electrospray ionization tandem mass spectrometry.
Correction of preoperative vitamin D deficiency after Roux-en-Y gastric bypass surgery.
Factors that influence the cutaneous synthesis and dietary sources of vitamin D.
Vitamin D2 from irradiated mushrooms significantly increases femur bone mineral density in rats.
Bioavailability of vitamin D2 from irradiated mushrooms: an in vivo study.
[Enhanced ergosterol production by recombinant Saccharomyces cerevisiae 1190 harboring Vitreoscilla hemoglobin gene (vgb)].
Bioavailability of vitamin D from fortified process cheese and effects on vitamin D status in the elderly.
[Vitamin D supplementation for chronic kidney disease according to the guideline issued by DOQI].
Conversion of vitamin D3 to 1alpha,25-dihydroxyvitamin D3 by Streptomyces griseolus cytochrome P450SU-1.
Effect of vitamin D2- and D3-enriched diets on egg vitamin D content, production, and bird condition during an entire production period.
Simultaneous quantification of vitamins A, D3 and E in fortified infant formulae by liquid chromatography-mass spectrometry.
Selective inhibition of mammalian DNA polymerase alpha by vitamin D2 and D3.
Vitamin D2 analog 19-nor-1,25-dihydroxyvitamin D2: antitumor activity against leukemia, myeloma, and colon cancer cells.
Determination of cholecalciferol (vitamin D3) in selected foods by liquid chromatography: NMKL collaborative study.
Stimulative effects of (22E,24R)-ergosta-7,22-diene-3beta,5alpha,6beta-triol from fruiting bodies of Tricholoma auratum, on a mouse osteoblastic cell line, MC3T3-E1.
Fish as a major source of vitamin D in the Japanese diet.
Severe nutritional deficiencies in toddlers resulting from health food milk alternatives.
[Vitamin D deficiency among immigrants].
Comparison of commercially available (125)I-based RIA methods for the determination of circulating 25-hydroxyvitamin D.
Vitamin D in an ecological context.
Binding of lipophilic nutrients to beta-lactoglobulin prepared by bioselective adsorption.
Simultaneous determination of fat-soluble vitamins A, D and E and pro-vitamin D2 in animal feeds by one-step extraction and high-performance liquid chromatography analysis.
Chicken parathyroid hormone gene expression in response to gastrin, omeprazole, ergocalciferol, and restricted food intake.
Binding of vitamin D and cholesterol to beta-lactoglobulin.
[Fortified milk and supplements of oral vitamin D. Comparison of the effect of two doses of vitamin D (500 and 1,000 UI/d) during the first trimester of life].
The dietary requirement of juvenile grass shrimp (Penaeus monodon) for vitamin D.
A large dose of ergocalciferol does not cause deficient blood coagulation but is extremely toxic to rats.
Ketodiet, physiological calcium intake and native vitamin D improve renal osteodystrophy.
[Determination of vitamin D in food using high performance liquid chromatography (HPLC). Results of collaborating studies of the working group "Vitamin Analysis" according to section 35 of the German Food Act].
The vitamin D content of fortified milk and infant formula.
Hypervitaminosis D associated with drinking milk.
Effects of ergocalciferol supplementation on the concentration of vitamin D and its metabolites in human milk.
Liquid chromatographic determination of vitamin D in infant formula.
Determination of vitamin D3 in margarines, oils and other supplemented food products using HPLC.
[Changes in organ-specific enzymes under the influence of an enriched food ration in experimental cadmium poisoning].
A prospective trial of the effect of vitamin D supplementation on metacarpal bone loss in elderly women.
Liquid chromatographic determination of vitamin D in milk and infant formula.
Effect of various vitamin D analogs on plasma calcium and phosphorus and intestinal calcium absorption in fed and unfed American eels, Anguilla rostrata.
[Comparative antirachitic activity of vitamins D2 and D3 in the body of chicks].
Plasma levels of 25-hydroxyvitamin D2 and 25-hydroxyvitamin D3 in maternal, cord and neonatal blood.
Simplified assay of vitamin D2 in fortified dried milk by using two steps of high-performance liquid chromatography.
Nutrition imbalance and angiotoxins as dietary risk factors in coronary heart disease.
Prevention of vitamin-D deficiency in Asians.
Vitamin D2 and cholesterolemia in the growing rat.
RICKETS RECURS IN BRITISH CHILDREN.
[On the problem of the clarification of rational methods of vitamin-enrichment of food for children with vitamin D2].
Treatment of parathyroid tetany with vitamin D2.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
Metabolomics Database:Search
KEGG (GenomeNet):C05441
HMDB (The Human Metabolome Database):HMDB00900
FooDB:FDB012811
Export Tariff Code:2936.29.5020
FDA Listing of Food Additive Status:View
VCF-Online:VCF Volatile Compounds in Food
Wikipedia:View
Formulations/Preparations:
•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 unitsml) of the vitamin in propylene glycol is also available. an injection in oil (500,000 unitsml) 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 mgml) & a soln in oil (0.2 mgml). •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.

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 396.65786743164
Melting Point 116 to 117°C @ 760 mm Hg
logP (o/w) 10.44 est
Solubility
water, 50 mg/L @ 25 °C (exp) Yes

Occurrences

Safety Information

Safety information

Preferred SDS: View
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 10000 mg/kg
"Agricultural Chemicals," Thomson, W.T., 4 vols., Fresno, CA, Thomson Publications, 1976/77 revisionVol. 3, Pg. 132,1986

oral-mouse LD50 23.70 mg/kg
Pesticide Manual. Vol. 9, Pg. 115, 1991.

oral-cat LDLo 5 mg/kg
Drugs in Japan Vol. 6, Pg. 128, 1982.

intramuscular-dog LDLo 5 mg/kg
Zeitschrift fuer die Gesamte Experimentelle Medizin. Vol. 116, Pg. 138, 1950.

intraperitoneal-dog LDLo 10 mg/kg
GASTROINTESTINAL: NAUSEA OR VOMITING BEHAVIORAL: FLUID INTAKE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Zeitschrift fuer die Gesamte Experimentelle Medizin. Vol. 116, Pg. 138, 1950.

intravenous-dog LDLo 5 mg/kg
Zeitschrift fuer die Gesamte Experimentelle Medizin. Vol. 116, Pg. 138, 1950.

oral-dog LDLo 4 mg/kg
GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" GASTROINTESTINAL: NAUSEA OR VOMITING BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Zeitschrift fuer die Gesamte Experimentelle Medizin. Vol. 116, Pg. 138, 1950.

oral-duck LD50 > 2000 mg/kg
Defense des Vegetaux. Vol. 43(255-256), Pg. 14, 1989.

oral-guinea pig LDLo 40 mg/kg
Drugs in Japan Vol. 6, Pg. 128, 1982.

oral-mouse LD50 23700 ug/kg
Pesticide Manual. Vol. 9, Pg. 115, 1991.

oral-rat LD50 10 mg/kg
"Agricultural Chemicals," Thomson, W.T., 4 vols., Fresno, CA, Thomson Publications, 1976/77 revisionVol. 3, Pg. 132, 1986.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
nutrient supplements
Recommendation for vitamin D2 usage levels up to:
not for fragrance use.
Recommendation for vitamin D2 flavor usage levels up to:
not for flavor use.

Safety references

European Food Safety Authority (EFSA) reference(s):

Safety of vitamin D2 mushroom powder as a novel food pursuant to Regulation (EU) 2015/2283
View page or View pdf

Safety of Vitamin D mushroom powder (Agaricus bisporus) as a Novel food pursuant to Regulation (EU) 2015/2283
View page or View pdf

EPI System: View
ClinicalTrials.gov:search
Daily Med:search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
Carcinogenic Potency Database:Search
EPA Substance Registry Services (TSCA):50-14-6
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5280793
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
(1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan
Chemidplus:0000050146
EPA/NOAA CAMEO:hazardous materials
RTECS:KE1050000 for cas# 50-14-6