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50-14-6 分子结构
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(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编号:39
分子式:C28H44O
平均质量:396.64836
单一同位素质量:396.33921603
SMILES和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

引用这个纪录

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

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(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传统名
ergocalciferol
商标名
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
别名
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
(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
Vitamin D2
Synthetic Vitamin D
Ergocalciferol
Ergocalciferol
CAS号
50-14-6
EC号
200-014-9
MDL号
MFCD00166988
Beilstein号
1916682
PubChem SID
24894344
160963502
46505053
PubChem CID
5280793

数据来源

数据来源

所有数据来源 商品来源 非商品来源

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 18.384342  质子受体
质子供体 LogD (pH = 5.5) 7.050558 
LogD (pH = 7.4) 7.050558  Log P 7.050558 
摩尔折射率 128.8897 cm3 极化性 49.86576 Å3
极化表面积 20.23 Å2 可自由旋转的化学键
里宾斯基五规则 false 
Log P 7.59  LOG S -5.96 
溶解度 4.33e-04 g/l 

分子性质

分子性质

理化性质 安全信息 产品相关信息 生物活性(PubChem)
溶解度
0.05 mg/mL [TOMLIN,C (1994)] expand 查看数据来源
Acetone expand 查看数据来源
Chloroform expand 查看数据来源
DMSO expand 查看数据来源
Do you have solubility information on this product that you would like to share? expand 查看数据来源
Ethanol expand 查看数据来源
Methanol expand 查看数据来源
外观
White Solid expand 查看数据来源
熔点
114-118 °C(lit.) expand 查看数据来源
115-118°C expand 查看数据来源
疏水性(logP)
7.3 expand 查看数据来源
保存条件
Amber Vial, -20°C Freezer expand 查看数据来源
RTECS编号
KE1050000 expand 查看数据来源
欧盟危险性物质标志
剧毒(Highly toxic) 剧毒(Highly toxic) (T+) expand 查看数据来源
联合国危险货物编号
2811 expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
德国WGK号
2 expand 查看数据来源
联合国危险货物等级
6.1 expand 查看数据来源
联合国危险货物包装类别(PG)
2 expand 查看数据来源
危险公开号
24/25-26-48/25 expand 查看数据来源
安全公开号
28-36/37-45 expand 查看数据来源
GHS危险品标识
GHS06 expand 查看数据来源
GHS08 expand 查看数据来源
GHS警示词
Danger expand 查看数据来源
GHS危险声明
H301-H311-H330-H372 expand 查看数据来源
GHS警示性声明
P260-P280-P284-P301 + P310-P310 expand 查看数据来源
个人保护装置
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 查看数据来源
RID/ADR
UN 2811 6.1/PG 2 expand 查看数据来源
保存温度
2-8°C expand 查看数据来源
级别
Sigma Reference Standard expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
包装
ampule of 250 mg expand 查看数据来源

详细说明

详细说明

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 -  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.
Sigma Aldrich -  E1007 external link
包装
Packaged in flame-sealed ampules under Argon
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.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • DeLuca HF: Overview of general physiologic features and functions of vitamin D. Am J Clin Nutr. 2004 Dec;80(6 Suppl):1689S-96S. Pubmed
  • 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)
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专利

专利

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