天然ビタミン E

エレビットホルト · エビオン · トコフェロール · エクアソールE · 天然ビタミン E · ビタミンE · Mixed Tocopherols · A-TOCOPHEROL

https://huagongshe.com/ja/chemical/14985

識別子と物理属性

CAS No.	1406-18-4
分子式	C29H50O2
平均分子量	430.7 g/mol
単同位体質量	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
現地名	天然ビタミン E

化学・物理的性質

XLogP	10.7
極性表面積	29.5
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
形式電荷	0
複雑度	503
物質分類	Biological Agents -> Vitamins and Derivatives
医薬品	Pharmaceuticals -> Listed in ZINC15
脂質	Lipids -> Prenol Lipids [PR] -> Quinones and hydroquinones [PR02] -> Vitamin E [PR0202]
SpringerMaterials Properties	Chemical diffusion
香料	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
融点	3 °C292 °C
蒸気圧	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 Å² [M-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]208.9 Å² [M-H]-
貯蔵条件	0-6°C
溶解度	可溶((CH3)2CO, エタノール, CHCl3, (C2H5)2O), 不溶(水)
臭い	代表的な植物油
化粧品成分の機能	香料皮膚コンディショニング - 閉塞性スキンコンディショニング - その他抗酸化物質
LogP（分配係数）	10.962 (est)
CAS データベース	1406-18-4(CAS DataBase Reference)
NISTの化学物質情報	«alpha»-Tocopherol(1406-18-4)
EPAの化学物質情報	Vitamin E (1406-18-4)

化学的特性

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.

化学性质

トコフェロールはフェノール性の水酸基を持つクロマノール環という特徴的な構造を持っていますこの構造によりトコフェロールは細胞膜を保護することにより細胞を酸化ストレスから守る能力を持っていますまたトコフェロールは脂溶性であり体内の脂質と容易に結びつくことができます

安全性と法規制

GHS 分類	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]
規制情報	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
その他の安全情報	Evaluation - Tocopherols and their salts and esters
有害性の概要	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
暴露経路	Oral, Topical, Intramuscular 50 to 80% absorbed from gastrointestinal tract.
毒性の概要	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.

用途

解説

動物の健全な妊娠分娩に必要な，ビタミンE作用を有するトコールのメチル誘導体．メチル基の数と位置により，α-，β-，γ-，δ-トコフェロールなどとよばれる．小麦胚芽油，綿実油，大豆油などの植物油に0.1～0.3％含まれている．2位の不斉炭素に関し，天然品はR形である．α-，β-，そのほかのトコフェロールのビタミンE活性は約100：33：1である．ビタミンEの国際単位は(±)-α-トコフェロールの酢酸エステル1 mg に相当する．

使用

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.

使用用途

トコフェロールの主な使用用途は、サプリメントの主成分、動物用飼料の添加剤などです。その他、酸化防止のための微量添加物として使用される場合もあります。例として、食品または化粧品の酸化防止剤などが挙げられます。トコフェロールは、酸化防止効果を利用して、アンチエイジングを目的とした製品に使用される場合があります。1日あたりの推奨摂取量は、年齢や性別によって異なりますが6.0mg～6.5mg/日です。油溶性で体内に蓄積しやすく、過剰に摂取すると健康被害をおよぼす可能性があるため注意が必要です。

製法・合成法

製造方法

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.