Grundinformationen
- Standard-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- Summenformel
- C29H50O2
- Durchschnittliche Molmasse
- 430,7 g/mol
- Monoisotopische Masse
- 430,38108084
Überblick
(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.
Namen und Bezeichner
- Bevorzugter Name
- alpha-Tocopherol
- IUPAC
- (2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol
- Lokaler Name
- Vitamin E
- Englischer Name
- Tocopherol
- Summenformel
- C29H50O2
- Molmasse
- 430.71
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
1406-18-4、2074-53-5、59-02-9- PubChem CID
- 14985
- DTXSID
DTXSID0026339- ChEMBL
CHEMBL47- ChEBI
CHEBI:18145- UNII
- N9PR3490H9
- EC Number
- 200-412-2、215-798-8、218-197-9、606-803-8
- Nikkaji
- J24.260H
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 10,7
- Polarare Oberfläche (TPSA)
- 29,5 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 12
- Schwere Atome
- 31
- Formalladung
- 0
- Komplexität
- 503
Experimentelle und physikochemische Eigenschaften
Physical Description
Liquid
Transparent solid; mp = 2.5-3.5 deg C; [Merck Index] Pale yellow viscous liquid; [HSDB] Light yellow viscous liquid; [Sigma-Aldrich MSDS]
Liquid
Collision Cross Section
208.52 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
208.9 Ų [M-H]-
Physikochemische Eigenschaften
- Schmelzpunkt
- 292 °C · 292 °C
- storage temp.
- 0 · 0-6°C
- Löslichkeit
- 3 · Soluble ((CH3)2CO, ethanol, CHCl3, (C2H5)2O), insoluble (water)
- Geruch (Odor)
- Typical vegetable oil
- Kosmetik-Inhaltsstoffe Funktionen
- FRAGRANCESKIN CONDITIONING - OCCLUSIVESKIN CONDITIONING - MISCELLANEOUSANTIOXIDANT
- LogP
- 10.962 · 10.962 (est)
- CAS Datenbank
- 1406 · 1406-18-4(CAS DataBase Reference)
- NIST chemische Informationen
- «alpha»-Tocopherol(1406-18-4)
- EPA chemische Informationen
- Vitamin E (1406-18-4)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
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]
Gefahrenhinweise
Regulatory Information
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
Evaluation - Tocopherols and their salts and esters
Evaluation - Tocopherols and their salts and esters
Hazard Classes and Categories
Skin Sens. 1B (68.2%)
Not Classified
Toxikologische Informationen
Toxicity Summary
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.
Sicherheitsdaten
- tsca
- TSCA listed
Chemie und Industrie
Pharmakologische Informationen
Verwendung und Herstellung
Uses
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.
Use Classification
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
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
Anwendungen
VerwendenFat-soluble vitamin E, which is a light yellow oil readily degradable by heat. As a vitamin, it is essential for normal muscle growth and prevents vitamin A destruction by deterioration. It also functions as an antioxidant. It prevents the oxidation of certain fatty acids and is stable unless the food becomes rancid. Vegetable oils contain a higher concentration of natural antioxidants, including tocopherols, than animal fats and are thus more stable. Tocopherol is obtained from vegetable oils, beans, eggs, and milk. It is also termed alpha-tocopherol.
Darstellung
synthetischeTocopherol is synthesised in two ways. One is to extract it from natural plant sources and the other is to obtain it by chemical synthesis. The following are the chemical synthesis routes:The most important natural raw materials for production of tocopherols by extraction are deodoriser sludges, which are distillates obtained in the deodorisation of vegetable oils. Such distillates contain sterols, sterol esters and triacylglycerols, as well as tocopherols and tocotrienols. The concentration of tocopherols depends on the deodorisation parameters (temperature, vacuum, quantity of injected steam and equipment) but their amount is lower than 10%, usually 8–9 %, of unsaponifiable matter present. Separation of tocopherol from the other distilled compounds is possible by several methods: (1) by esterification with a lower alcohol, washing and vacuum distillation; (2) by saponification, or (3) by fractional liquid–liquid extraction. The concentrates obtained in this way may be purified further by molecular distillation, extraction, crystallisation, or combinations of these procedures.The tocopherol concentrates recommended as antioxidants are mixtures with relatively high contents of γ-tocopherol and δ-tocopherol (being obtained from soybean oil), but α-tocopherol is also present. The total tocopherol concentration usually lies between 30 and 80%. The rest is constituted of triacylglycerols.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Anbieter50 Anbieter
Ergänzende Hinweise
Definition(vitamin E). Any of a group of related substances (α-, β-, γ-, andΔ-tocopherol) that constitute vitamin E. The α-form (which occurs naturally as the d-isomer) is the most potent. Occurs naturally in plants, especially wheat germ. All are derivatives of dihydrobenzo-γ-pyran and differ from each other only in the number and position of methyl groups. Vitamin E is required by certain rodents for normal reproduction. Muscular and central nervous system depletion along with generalized edema are deficiency symptoms in all animals. It is not required as a dietary supplement for humans.
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