alpha-Tocopherol
Mixed Tocopherols · A-TOCOPHEROL · DL-TOCOPHEROL · RAC-ALPHA-TOCOPHEROL · ALL-RAC-ALPHA-TOCOPHEROL · DL-ALPHA TOCOPHERYL ACETATE 500 · (2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol · Erevit forte
식별자 및 물리적 특성
| CAS No. | 1406-18-4 |
|---|---|
| 분자식 | C29H50O2 |
| 평균 분자량 | 430.7 g/mol |
| 단동위원소 질량 | 430.38108084 g/mol |
| 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 |
| PubChem CID | 14985 |
| ChEMBL | CHEMBL47 |
| ChEBI | CHEBI:18145 |
| EC No. | 200-412-2 |
| DTXSID | DTXSID0026339 |
화학 및 물리적 성질
| XLogP | 10.7 |
|---|---|
| 극성 표면적 | 29.5 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 2 |
| 회전 가능 결합 수 | 12 |
| 무거운 원자 수 | 31 |
| 형식 전하 | 0 |
| 복잡도 | 503 |
| 물질 분류 | Biological Agents -> Vitamins and Derivatives |
| 의약품 | Pharmaceuticals -> Listed in ZINC15 |
| 지질 | Lipids -> Prenol Lipids [PR] -> Quinones and hydroquinones [PR02] -> Vitamin E [PR0202] |
| SpringerMaterials Properties | Chemical diffusion |
| 향료 | Fragrance 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 Disruptors | Potential endocrine disrupting compound |
| 녹는점 | 3 °C292 °C |
| 증기압 | 0.00000001 [mmHg] |
| Physical Description | LiquidTransparent solidmp = 2.5-3.5 deg C[Merck Index] Pale yellow viscous liquid[HSDB] Light yellow viscous liquid[Sigma-Aldrich MSDS] |
| Collision Cross Section | 208.52 Ų [M-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]208.9 Ų [M-H]- |
| 저장 조건 | 0-6°C |
| 용해도 | Soluble ((CH3)2CO, ethanol, CHCl3, (C2H5)2O), insoluble (water) |
| 냄새 | 대표적인 식물성 기름 |
| 화장품 원료 기능 | 향기피부 컨디셔닝 - 밀폐제피부 컨디셔닝 - 기타항산화제 |
| LogP(분배 계수) | 10.962 (est) |
| NIST | «alpha»-Tocopherol(1406-18-4) |
| EPA | Vitamin E (1406-18-4) |
화학적 성질
Viscous oils. Soluble in fats; insoluble in water. Stable to heat in the absence of oxygen, to strong acids, and to visible light; unstable to UV light, alkalies, and oxidation.
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for 92.8% (270 of 291) of all reports.Not ClassifiedAggregated 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.WarningH317 (68.2%): May cause an allergic skin reaction [Warning Sensitization, Skin] |
|---|---|
| 규제 정보 | 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/112022H-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 |
| 기타 안전 정보 | Evaluation - Tocopherols and their salts and esters |
| 유해성 요약 | Acceptable 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 Chemical | Chemical: alpha-Tocopherol |
| Hazard Classes and Categories | Skin Sens. 1B (68.2%)Not Classified |
| 노출 경로 | Oral, Topical, Intramuscular 50 to 80% absorbed from gastrointestinal tract. |
| 독성 요약 | 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 Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| TSCA 등재 상태 | TSCA listed |
용도
용도
Fat-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.
제조 및 합성 방법
제조 방법
Tocopherol 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.