alpha-Tocopherol

HCID 178798168

基本情報

CAS
21-59-0
標準SMILES
Cc1c(C)c2c(c(C)c1O)CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)C)O2
InChIKey
GVJHHUAWPYXKBD-IEOSBIPESA-N
分子式
C29H50O2
平均分子量
430.7 g/mol

概要

(R,R,R)-alpha-tocopherol is an alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils. It has a role as an antioxidant, an antiviral agent, a micronutrient, an EC 2.7.11.13 (protein kinase C) inhibitor, an anticoagulant, a nutraceutical, an immunomodulator, an antiatherogenic agent, a plant metabolite and an algal metabolite. It is an enantiomer of a (S,S,S)-alpha-tocopherol.

名称と識別子

優先名称
alpha-Tocopherol
IUPAC
(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol
英語名
DL-alpha-Tocopherol
分子量
0

名称と別名

alpha-Tocopherol59-02-9D-alpha-Tocopherol5,7,8-Trimethyltocol(+)-alpha-Tocopherol2074-53-5PhytogermineEprolin(R,R,R)-alpha-Tocopherola-Vitamin EDenamoneViteolin
名称をさらに表示
VITAMIN E 50% ( DC GRADE)VITAMIN E (D-ALPHA-TOCOPHERYL ACETATE)
EtavitEsorb(2R,4'R,8'R)-alpha-Tocopherolalpha Tocopherolalpha-Vitamin EAquasol Ealpha-Tocopherol, D-d-a-tocopherol

データベース識別子

CAS
21-59-0
ChEMBL
CHEMBL47
ChEBI
CHEBI:18145
UNII
N9PR3490H9
EC Number
200-412-2、218-197-9
Nikkaji
J24.260H

物性

構造計算による物性

XLogP
10.7
極性表面積
29.5 Ų
水素結合供与体数
1
水素結合受容体数
2
回転可能結合数
12
重原子数
31

実験および物理化学的性質

Chemical ClassesBiological Agents -> Vitamins and Derivatives
DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Prenol Lipids [PR] -> Quinones and hydroquinones [PR02] -> Vitamin E [PR0202]
SpringerMaterials PropertiesChemical diffusion
FragrancesFragrance Ingredient (2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)-) -> IFRA transparency List
Endocrine DisruptorsPotential endocrine disrupting compound

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 92.8% (270 of 291) of all reports.

Not Classified

Aggregated GHS information provided per 291 reports by companies from 4 notifications to the ECHA C&L Inventory.

This chemical does not meet GHS hazard criteria for 31.8% (7 of 22) of reports.

Warning

H317 (68.2%): May cause an allergic skin reaction [Warning Sensitization, Skin]

危険有害性情報

Regulatory Information · 6 件

Chemical: 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, [2R-[2R*(4R*,8R*)]]-

Chemical: 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, [2R*(4R*,8R*)]-(.+-.)-

Regulation (EC) No 1831/2003 (amended)

2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 13-11-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/11202

2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4R,8R)-4,8,12-trimethyltridecyl-, (2R)-rel-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety Information · 2 件

Evaluation - Tocopherols and their salts and esters

Evaluation - Tocopherols and their salts and esters

Hazards SummaryAcceptable daily intake (ADI) of 0.15-2 mg/kg; [JECFA] Excessive, chronic ingestion can cause nausea, headaches, and weakness. [Olson, p. 446] May cause irritation; [Sigma-Aldrich MSDS]
EPA Safer ChemicalChemical: alpha-Tocopherol
Hazard Classes and Categories · 2 件

Skin Sens. 1B (68.2%)

Not Classified

毒性情報

Exposure RoutesOral, Topical, Intramuscular 50 to 80% absorbed from gastrointestinal tract.
Toxicity Summary · 1 件

Although all forms of Vitamin E exhibit antioxidant activity, it is known that the antioxidant activity of vitamin E is not sufficient to explain the vitamin's biological activity. <br/>Vitamin E's anti-atherogenic activity involves the inhibition of the oxidation of LDL and the accumulation of oxLDL in the arterial wall. It also appears to reduce oxLDL-induced apoptosis in human endothelial cells. Oxidation of LDL is a key early step in atherogenesis as it triggers a number of events which lead to the formation of atherosclerotic plaque. In addition, vitamin E inhibits protein kinase C (PKC) activity. PKC plays a role in smooth muscle cell proliferation, and, thus, the inhibition of PKC results in inhibition of smooth muscle cell proliferation, which is involved in atherogenesis. <br/>Vitamin E's antithrombotic and anticoagulant activities involves the downregulation of the expression of intracellular cell adhesion molecule(ICAM)-1 and vascular cell adhesion molecule(VCAM)-1 which lowers the adhesion of blood components to the endothelium. In addition, vitamin E upregulates the expression of cytosolic phospholipase A2 and cyclooxygenase (COX)-1 which in turn enhances the release of prostacyclin. Prostacyclin is a vasodilating factor and inhibitor of platelet aggregation and platelet release. It is also known that platelet aggregation is mediated by a mechanism involving the binding of fibrinogen to the glycoprotein IIb/IIIa (GPIIb/IIIa) complex of platelets. GPIIb/IIIa is the major membrane receptor protein that is key to the role of the platelet aggregation response. GPIIb is the alpha-subunit of this platelet membrane protein. Alpha-tocopherol downregulates GPIIb promoter activity which results in reduction of GPIIb protein expression and decreased platelet aggregation. Vitamin E has also been found in culture to decrease plasma production of thrombin, a protein which binds to platelets and induces aggregation. A metabolite of vitamin E called vitamin E quinone or alpha-tocopheryl quinone (TQ) is a potent anticoagulant. This metabolite inhibits vitamin K-dependent carboxylase, which is a major enzyme in the coagulation cascade.<br/>The neuroprotective effects of vitamin E are explained by its antioxidant effects. Many disorders of the nervous system are caused by oxidative stress. Vitamin E protects against this stress, thereby protecting the nervouse system. <br/>The immunomodulatory effects of Vitamin E have been demonstrated in vitro, where alpha-tocopherol increases mitogenic response of T lymphocytes from aged mice. The mechanism of this response by vitamin E is not well understood, however it has been suggested that vitamin E itself may have mitogenic activity independent of its antioxidant activity. <br/>Lastly, the mechanism of action of vitamin E's antiviral effects (primarily against HIV-1) involves its antioxidant activity. Vitamin E reduces oxidative stress, which is thought to contribute to HIV-1 pathogenesis, as well as to the pathogenesis of other viral infections. Vitamin E also affects membrane integrity and fluidity and, since HIV-1 is a membraned virus, altering membrane fluidity of HIV-1 may interfere with its ability to bind to cell-receptor sites, thus decreasing its infectivity.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

化学と産業

薬理情報

Metabolism/MetabolitesHepatic.
Tissue LocationsAdipose Tissue
Cellular LocationsCytoplasm

用途と製造

Uses · 3 件

The bioactive natural form of vitamin E found in green vegetables, grains, and oils (especially palm, safflower, and sunflower); Used as an antioxidant in oils and as a vitamin E supplement; [Merck Index] Used as a medication and animal feed additive; [HSDB]

Farming (Feed Additives) [Category: Industry]

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.

U.S. Production2023: 21,006 lb
Consumer UsesFragrance
Industry UsesFragrance
Use Classification · 6 件

EPA Safer Chemical Functional Use Classes -> Preservatives and Antioxidants

Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern

Fragrance Ingredients

Food Additives -> ANTIOXIDANT; NUTRIENT_SUPPLEMENT -> JECFA Functional Classes

Food Additives -> ANTIOXIDANT; NUTRIENT_SUPPLEMENT -> JECFA Functional Classes

Food Additives -> ANTIOXIDANT; NUTRIENT_SUPPLEMENT -> JECFA Functional Classes

General Manufacturing Information · 2 件

Soap, Cleaning Compound, and Toilet Preparation Manufacturing

2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)-: ACTIVE

サプライヤー3 社

湖北远成药业有限公司18062666904 · [email protected]
成都润泽本土化工有限公司13096311329 028-88469284 616445927 · [email protected]
Alfa Chemistry+1-5166625404 · [email protected]

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