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59-02-9 分子结构
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(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol

ChemBase编号:49
分子式:C29H50O2
平均质量:430.7061
单一同位素质量:430.38108084
SMILES和InChIs

SMILES:
O1[C@](CCC[C@@H](CCC[C@@H](CCCC(C)C)C)C)(CCc2c1c(c(c(O)c2C)C)C)C
Canonical SMILES:
C[C@@H](CCC[C@]1(C)CCc2c(O1)c(C)c(c(c2C)O)C)CCC[C@@H](CCCC(C)C)C
InChI:
InChI=1S/C29H50O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h20-22,30H,9-19H2,1-8H3/t21-,22-,29-/m1/s1
InChIKey:
GVJHHUAWPYXKBD-IEOSBIPESA-N

引用这个纪录

CBID:49 http://www.chembase.cn/molecule-49.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
(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol
IUPAC传统名
VitaE
vitamin E
商标名
Amino-Opti-E
Aquasol E
Daltose
E-200 I.U. Softgels
E-Complex-600
E-Ferol
E-Vitamin succinate
Gordo-Vite E
Vitamin Plus E Softgells
Vitec
别名
2,5,7,8-Tetramethyl-2-(4′,8′,12′-trimethyltridecyl)-6-chromanol
5,7,8-Trimethyltocol
D-α-Tocopherol
Vitamin E
(+)-α-Tocopherol
Alpha-Tocopherol
(2R)-3,4-Dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol
(+)-α-Tocopherol
(all-R)-α-Tocopherol
Acros
Almefrol
Biopass E 20
Optovit
Tocovital
α-Vitamin E
α-Tocopherol
alpha-Tocopherol
Tocopherol
Vitamin E
a-Vitamin E
α-Tocopherol
CAS号
59-02-9
EC号
200-412-2
MDL号
MFCD00072045
Beilstein号
4712525
PubChem SID
46506524
160963512
24900154
24899979
PubChem CID
14985
CHEBI ID
18145
ATC码
A11HA03
CHEMBL
47
Chemspider ID
14265
DrugBank ID
DB00163
美国药典/FDA物质标识码
N9PR3490H9
维基百科标题
Alpha-Tocopherol

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 10.802178  质子受体
质子供体 LogD (pH = 5.5) 10.507715 
LogD (pH = 7.4) 10.507546  Log P 10.507717 
摩尔折射率 135.3741 cm3 极化性 52.98319 Å3
极化表面积 29.46 Å2 可自由旋转的化学键 12 
里宾斯基五规则 false 
Log P 8.84  LOG S -7.79 
溶解度 7.04e-06 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
Chloroform expand 查看数据来源
Ethanol expand 查看数据来源
Insoluble in water, but water-dispersible. expand 查看数据来源
Methanol expand 查看数据来源
外观
clear yellow liquid expand 查看数据来源
clear yellow neat (liquid, ≥0.88M based on potency, density and molecular wt.) expand 查看数据来源
clear yellow to red expand 查看数据来源
Oil expand 查看数据来源
Pale Yellow Thick Oil expand 查看数据来源
yellow-brown viscous liquid expand 查看数据来源
熔点
2.5–3.5 °C expand 查看数据来源
沸点
200-220 °C/0.1 mmHg(lit.) expand 查看数据来源
200–220 °C at 0.1 mmHg expand 查看数据来源
闪点
110 °C expand 查看数据来源
230 °F expand 查看数据来源
密度
0.95 g/mL at 25 °C(lit.) expand 查看数据来源
0.950 g/cm3 expand 查看数据来源
折射率
n20/D 1.505(lit.) expand 查看数据来源
疏水性(logP)
10 expand 查看数据来源
保存条件
-20°C Freezer expand 查看数据来源
RTECS编号
DJ2900000 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
1 expand 查看数据来源
NFPA704
NFPA 704 diagram
1
1
0
expand 查看数据来源
个人保护装置
Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US) expand 查看数据来源
保存温度
-20°C expand 查看数据来源
2-8°C expand 查看数据来源
纯度
95+% expand 查看数据来源
药效
≥600 mg d-α-tocopherol per g expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
适用性
suitable for insect cell culture expand 查看数据来源
生物来源
from vegetable oil expand 查看数据来源
产品类型
Type V expand 查看数据来源
Type VI expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank -  DB00163 external link
Item Information
Drug Groups approved; nutraceutical
Description A generic descriptor for all tocopherols and tocotrienols that exhibit alpha-tocopherol activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of isoprenoids. [PubChem]
Indication Vitamin E, known for its antioxidant activities, is protective against cardiovascular disease and some forms of cancer and has also demonstrated immune-enhancing effects. It may be of limited benefit in some with asthma and rheumatoid arthritis. It may be helpful in some neurological diseases including Alzheimer's, some eye disorders including cataracts, and diabetes and premenstrual syndrome. It may also help protect skin from ultraviolet irradiation although claims that it reverses skin aging, enhances male fertility and exercise performance are poorly supported. It may help relieve some muscle cramps.
Pharmacology Vitamin E has antioxidant activity. It may also have anti-atherogenic, antithrombotic, anticoagulant, neuroprotective, antiviral, immunomodulatory, cell membrane-stabilizing and antiproliferative actions. Vitamin E is a collective term used to describe eight separate forms, the best-known form being alpha-tocopherol. Vitamin E is a fat-soluble vitamin and is an important antioxidant. It acts to protect cells against the effects of free radicals, which are potentially damaging by-products of the body's metabolism. Vitamin E is often used in skin creams and lotions because it is believed to play a role in encouraging skin healing and reducing scarring after injuries such as burns. There are three specific situations when a vitamin E deficiency is likely to occur. It is seen in persons who cannot absorb dietary fat, has been found in premature, very low birth weight infants (birth weights less than 1500 grams, or 3½ pounds), and is seen in individuals with rare disorders of fat metabolism. A vitamin E deficiency is usually characterized by neurological problems due to poor nerve conduction. Symptoms may include infertility, neuromuscular impairment, menstrual problems, miscarriage and uterine degradation. Preliminary research has led to a widely held belief that vitamin E may help prevent or delay coronary heart disease. Antioxidants such as vitamin E help protect against the damaging effects of free radicals, which may contribute to the development of chronic diseases such as cancer. It also protects other fat-soluble vitamins (A and B group vitamins) from destruction by oxygen. Low levels of vitamin E have been linked to increased incidence of breast and colon cancer.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic.
Absorption 50 to 80% absorbed from gastrointestinal tract.
Protein Binding Bound to beta-lipoproteins in blood.
References
Iuliano L, Micheletta F, Maranghi M, Frati G, Diczfalusy U, Violi F: Bioavailability of vitamin E as function of food intake in healthy subjects: effects on plasma peroxide-scavenging activity and cholesterol-oxidation products. Arterioscler Thromb Vasc Biol. 2001 Oct;21(10):E34-7. [Pubmed]
Miller ER 3rd, Pastor-Barriuso R, Dalal D, Riemersma RA, Appel LJ, Guallar E: Meta-analysis: high-dosage vitamin E supplementation may increase all-cause mortality. Ann Intern Med. 2005 Jan 4;142(1):37-46. Epub 2004 Nov 10. [Pubmed]
Horwitt MK, Elliott WH, Kanjananggulpan P, Fitch CD: Serum concentrations of alpha-tocopherol after ingestion of various vitamin E preparations. Am J Clin Nutr. 1984 Aug;40(2):240-5. [Pubmed]
Rumbold AR, Crowther CA, Haslam RR, Dekker GA, Robinson JS: Vitamins C and E and the risks of preeclampsia and perinatal complications. N Engl J Med. 2006 Apr 27;354(17):1796-806. [Pubmed]
Poston L, Briley AL, Seed PT, Kelly FJ, Shennan AH: Vitamin C and vitamin E in pregnant women at risk for pre-eclampsia (VIP trial): randomised placebo-controlled trial. Lancet. 2006 Apr 8;367(9517):1145-54. [Pubmed]
Linus Pauling Institute / [Link]
External Links
Wikipedia
PDRhealth
Drugs.com
Sigma Aldrich -  T4389 external link
Other Notes
Mixed isomers
Quality
Approx. 400 mg of D-α-tocopherol per gram.The non-α-content varies from 5-50 mg per gram, the remainder is soybean oil.
Sigma Aldrich -  T1539 external link
Application
Use in insect cell culture applications as an antioxidant.
Other Notes
Mixed isomers
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. T1539.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Sigma Aldrich -  T3634 external link
Caution
Subject to air oxidation.
Other Notes
Mixed isomers
包装
Packaged under argon in a sealed ampule.
Quality
Approx. 670 mg D-α-tocopherol per gram. The non-α content is typically between 5-35 mg/g
Biochem/physiol Actions
Tocopherols (TCP) (vitamin E) are a series (α, β, γ and δ) of chiral organic molecules that vary in their degree of methylation of the phenol moiety of the chromanol ring. Tocopherols are lipid soluble anti-oxidants that protect cell membranes from oxidative damage. α-Tocopherol is the form of tocopherol preferentially absorbed by homo sapiens. Various isofroms and analogues of tocopherol have opposing and differentiated regulatory activities in vivo.
Physical properties
This product is miscible with chloroform or ethanol. It is practically insoluble in water but it is miscible with ether, acetone, and vegetable oils. It is unstable to alkaline conditions.
Toronto Research Chemicals -  T526125 external link
α-Tocopherol is the most bioactive of the naturally occurring forms of Vitamin E. Richest sources are green vegetables, grains, and oils, particularly palm, safflower and sunflower oils.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Linus Pauling Institute Link/
  • Iuliano L, Micheletta F, Maranghi M, Frati G, Diczfalusy U, Violi F: Bioavailability of vitamin E as function of food intake in healthy subjects: effects on plasma peroxide-scavenging activity and cholesterol-oxidation products. Arterioscler Thromb Vasc Biol. 2001 Oct;21(10):E34-7. Pubmed
  • Miller ER 3rd, Pastor-Barriuso R, Dalal D, Riemersma RA, Appel LJ, Guallar E: Meta-analysis: high-dosage vitamin E supplementation may increase all-cause mortality. Ann Intern Med. 2005 Jan 4;142(1):37-46. Epub 2004 Nov 10. Pubmed
  • Horwitt MK, Elliott WH, Kanjananggulpan P, Fitch CD: Serum concentrations of alpha-tocopherol after ingestion of various vitamin E preparations. Am J Clin Nutr. 1984 Aug;40(2):240-5. Pubmed
  • Rumbold AR, Crowther CA, Haslam RR, Dekker GA, Robinson JS: Vitamins C and E and the risks of preeclampsia and perinatal complications. N Engl J Med. 2006 Apr 27;354(17):1796-806. Pubmed
  • Poston L, Briley AL, Seed PT, Kelly FJ, Shennan AH: Vitamin C and vitamin E in pregnant women at risk for pre-eclampsia (VIP trial): randomised placebo-controlled trial. Lancet. 2006 Apr 8;367(9517):1145-54. Pubmed
  • Bianchi, G., et al.: Eur. J. Lipid Sci. Technology, 105, 229 (2003)
  • Sakouhi, F., et al.: Food Chem., 108, 833 (2003)
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专利

专利

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