Home > Compound List > Compound details
50-14-6 molecular structure
click picture or here to close

(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol

ChemBase ID: 39
Molecular Formular: C28H44O
Molecular Mass: 396.64836
Monoisotopic Mass: 396.33921603
SMILES and InChIs

SMILES:
O[C@@H]1C/C(=C/C=C\2/[C@H]3[C@@]([C@H](CC3)[C@H](C)/C=C/[C@@H](C(C)C)C)(CCC2)C)/C(=C)CC1
Canonical SMILES:
O[C@H]1CCC(=C)/C(=C\C=C\2/CCC[C@]3([C@H]2CC[C@@H]3[C@@H](/C=C/[C@@H](C(C)C)C)C)C)/C1
InChI:
InChI=1S/C28H44O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-20,22,25-27,29H,4,7-8,11,14-18H2,1-3,5-6H3/b10-9+,23-12+,24-13-/t20-,22+,25-,26+,27-,28+/m0/s1
InChIKey:
MECHNRXZTMCUDQ-RKHKHRCZSA-N

Cite this record

CBID:39 http://www.chembase.cn/molecule-39.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
IUPAC Traditional name
ergocalciferol
Brand Name
Buco-D
Calciferol
Calciferon 2
Condacaps
Condocaps
Condol
Crtron
Crystallina
D-Arthin
D-Tracetten
Daral
Davitamon D
Davitin
De-Rat Concentrate
Decaps
Dee-Osterol
Dee-Ron
Dee-Ronal
Dee-Roual
Deltalin
Deratol
Detalup
Diactol
Divit Urto
Doral
Drisdol
Ercalciol
Ergorone
Ergosterol, Irradiated
Ertron
Fortodyl
Geltabs
Hi-Deratol
Infron
Metadee
Mulsiferol
Mykostin
Novovitamin-D
Oleovitamin D
Oleovitamin D, Synthetic
Oleovitamin D2
Ostelin
Radiostol
Radstein
Radsterin
Rodine C
Shock-Ferol
Shock-Ferol Sterogyl
Sterogyl
Uvesterol-D
Vio-D
Viostdrol
Viosterol
Viosterol in Oil
Vitavel-D
Ergosterol Activated
Synonyms
Vitamin D2
Synthetic Vitamin D
Ergocalciferol
Ergocalciferol
(3β,5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-ol
Calciferol
Ercalciol
Ergosterol Irradiated
Ergocalciferol
Oleovitamin D2
Radiostol
Radsterin
(+)-Vitamin D2
Viosterol
Vio D
Vitavel-D
Vitamin D2
照射麦角甾醇
维生素 D2
钙化醇
骨化醇
麦角钙化醇
麦角钙化甾醇
CAS Number
50-14-6
EC Number
200-014-9
MDL Number
MFCD00166988
Beilstein Number
1916682
PubChem SID
160963502
24894344
46505053
PubChem CID
5280793

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 18.384342  H Acceptors
H Donor LogD (pH = 5.5) 7.050558 
LogD (pH = 7.4) 7.050558  Log P 7.050558 
Molar Refractivity 128.8897 cm3 Polarizability 49.86576 Å3
Polar Surface Area 20.23 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 7.59  LOG S -5.96 
Solubility (Water) 4.33e-04 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
0.05 mg/mL [TOMLIN,C (1994)] expand Show data source
Acetone expand Show data source
Chloroform expand Show data source
DMSO expand Show data source
Do you have solubility information on this product that you would like to share? expand Show data source
Ethanol expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
Melting Point
114-118 °C(lit.) expand Show data source
115-118°C expand Show data source
Hydrophobicity(logP)
7.3 expand Show data source
Storage Condition
Amber Vial, -20°C Freezer expand Show data source
RTECS
KE1050000 expand Show data source
European Hazard Symbols
Highly toxic Highly toxic (T+) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
2 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
2 expand Show data source
Risk Statements
24/25-26-48/25 expand Show data source
Safety Statements
28-36/37-45 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301-H311-H330-H372 expand Show data source
GHS Precautionary statements
P260-P280-P284-P301 + P310-P310 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 2811 6.1/PG 2 expand Show data source
Storage Temperature
2-8°C expand Show data source
Grade
Sigma Reference Standard expand Show data source
Certificate of Analysis
Download expand Show data source
Packaging
ampule of 250 mg expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00153 external link
Item Information
Drug Groups approved; nutraceutical
Description Ergocalciferol (Vitamin D2) is a derivative of ergosterol formed by ultraviolet rays breaking of the C9-C10 bond. It differs from cholecalciferol in having a double bond between C22 and C23 and a methyl group at C24. [PubChem]
Indication For use in the management of hypocalcemia and its clinical manifestations in patients with hypoparathyroidism, as well as for the treatment of familial hypophosphatemia (vitamin D resistant rickets). This drug has also been used in the treatment of nutritional rickets or osteomalacia, vitamin D dependent rickets, rickets or osteomalacia secondary to long-term high dose anticonvulsant therapy, early renal osteodystrophy, osteoporosis (in conjunction with calcium), and hypophosphatemia associated with Fanconi syndrome (with treatment of acidosis).
Pharmacology Ergoalcifediol (Vitamin D2) is a fat soluble steroid hormone precursor of vitamin D. The principal biologic function of vitamin D is the maintenance of normal levels of serum calcium and phosphorus in the bloodstream by enhancing the efficacy of the small intestine to absorb these minerals from the diet. Cholecalciferol is synthesized within our bodies naturally, but if UV exposure is inadequate or the metabolism of cholecalciferol is abnormal, then an exogenous source is required. Vitamin D2 is converted to 25-hydroxyvitamin D (25OHD) in the liver, and then to the active form, 1,25-dihydroxyvitamin D (1,25(OH)2D), in the kidney. Once transformed, it binds to the vitamin D receptor, which leads to a variety of regulatory roles. Vitamin D plays an important role in maintaining calcium balance and in the regulation of parathyroid hormone (PTH). It promotes renal reabsorption of calcium, increases intestinal absorption of calcium and phosphorus, and increases calcium and phosphorus mobilization from bone to plasma. Very few foods naturally contain vitamin D. Sources that contain the vitamin include fatty fish, the liver and fat of aquatic mammals (e.g., seals, polar bears), and eggs from chickens fed vitamin D-fortified feed. As such, many countries have instituted policies to fortify certain foods with vitamin D to compensate for the potentially low exposures of skin to sunlight. Vitamin D deficiency results in inadequate mineralization of bone or compensatory skeletal demineralization and causes decreased ionized calcium concentrations in blood and a resultant increase in the production and secretion of PTH. Increase in PTH stimulates the mobilization of skeletal calcium, inhibits renal excretion of calcium, and stimulates renal excretion of phosphorus. This results in normal fasting serum calcium concentrations and low or near-normal serum phosphorus. The enhanced mobilization of skeletal calcium induced by this secondary hyperparathyroidism leads porotic bone.
Toxicity LD50 = 23.7 mg/kg (Orally in mice); LD50 = 10 mg/kg (Orally in rats ); Nausea, vomiting and diarrhea, weight loss, irritability, weakness, fatigue, lassitude, and headache.
Affected Organisms
Humans and other mammals
Biotransformation Within the liver, ergocalciferol is hydroxylated to ercalcidiol (25-hydroxyergocalciferol) by the enzyme 25-hydroxylase. Within the kidney, ercalcidiol serves as a substrate for 1-alpha-hydroxylase, yielding ercalcitriol (1,25-dihydroxyergocalciferol), the biologically active form of vitamin D2.
Absorption Readily absorbed from small intestine (proximal or distal), requires presence of bile salts.
Half Life 19 to 48 hours (however, stored in fat deposits in body for prolonged periods).
Protein Binding >99.8%
References
DeLuca HF: Overview of general physiologic features and functions of vitamin D. Am J Clin Nutr. 2004 Dec;80(6 Suppl):1689S-96S. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Sigma Aldrich - E1007 external link
包装
Packaged in flame-sealed ampules under Argon
Sigma Aldrich - E5750 external link
Application
Do you have application information on this product that you would like to share?
包装
密封安瓿瓶。
Quantity
1 USP 单位 = 1 I.U.
Biochem/physiol Actions
Ergocalciferol (vitamin D2) and 25-Hydroxycholecalciferol (vitamin D3) are the two form of vitamin D which are activated in vivo by hydroxylation. Vitamin D2 and D3 may be used in a wide range of studies to assess their effects on function such as immune function and calcium homeostasis.
Toronto Research Chemicals - V676040 external link
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.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Knudson, B., et al.: J. Biol. Chem., 124, 287 (1938)
  • • Huber, B., et al.: J. Biol. Chem., 149, 125 (1938)
  • • Crowfoot, D., et al.: Nature, 162, 608 (1938)
  • • Suda, et al.: Biochem. Biophys. Res. Commun., 35, 182 (1938)
  • • DeLuca HF: Overview of general physiologic features and functions of vitamin D. Am J Clin Nutr. 2004 Dec;80(6 Suppl):1689S-96S. Pubmed
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle