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Tocopherols

HCID 14986
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
1406-66-2
표준 SMILES
Cc1c(O)cc2c(c1C)OC(C)(CCCC(C)CCCC(C)CCCC(C)C)CC2
InChIKey
QUEDXNHFTDJVIY-UHFFFAOYSA-N
분자식
C28H48O2
평균 분자량
416.7 g/mol
단동위원소 질량
416.36543078

개요

Tocopherol exists in four different forms designated as α, β, δ, and γ. They present strong antioxidant activities, and it is determined as the major form of vitamin E. Tocopherol, as a group, is composed of soluble phenolic compounds that consist of a chromanol ring and a 16-carbon phytyl chain. The classification of the tocopherol molecules is designated depending on the number and position of the methyl substituent in the chromanol ring. The different types of tocopherol can be presented trimethylated, dimethylated or methylated in the positions 5-, 7- and 8-. When the carbons at position 5- and 7- are not methylated, they can function as electrophilic centers that can trap reactive oxygen and nitrogen species. Tocopherols can be found in the diet as part of vegetable oil such as corn, soybean, sesame, and cottonseed. It is currently under the list of substances generally recognized as safe (GRAS) in the FDA for the use of human consumption.

이름 및 식별자

우선 이름
Tocopherols
IUPAC
2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydrochromen-6-ol
영어명
TOCOPHEROL
분자식
C28H48O2
분자량
416.67952

이름 및 동의어

Tocopherols1406-66-2MethyltocolsR0ZB2556P8LasarUnoVitVitaEVitamin EmpE VicotratMicorvit EE MulsinVitaPlus E
이름 더 보기
E 306D02332E-Mix 80E-Mix 60Tenox GTE-Mix 40AE-Oil 600E-Oil 700E-Oil 705
Vitamin E mpVitamin E-mpUno VitVitamin E DrageesDal EVitamin E, MowivitVitamin E, TogasanAntioxidans E-Hevert

데이터베이스 식별자

CAS
1406-66-2、7616-22-0
PubChem CID
14986
DTXSID
DTXSID5044075
ChEMBL
CHEMBL420898
UNII
ECY0XG64DO
EC Number
231-523-4、604-195-9
Nikkaji
J34.135E

물성

구조 계산 물성

XLogP
10.3
극성 표면적
29.5 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
2
회전 가능 결합 수
12
무거운 원자 수
30
형식 전하
0
복잡도
475

실험 및 물리화학적 성질

Cosmetics · 2건

Cosmetic ingredients (Tocopherol) -> CIR (Cosmetic Ingredient Review)

Skin conditioning; Antioxidant

Food AdditivesANTIOXIDANT, FLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT, NUTRIENT SUPPLEMENT -> FDA Substance added to food
SolubilityInsoluble
Boiling PointDecomposes

물리화학적 성질

밀도
0.93 g/mL · 0.930 g/mL at 25 °C
굴절률
20 · n20/D1.501
인화점
200 ℃ · >200℃
물리적 상태
Viscous
색상
Colorless to light yellow
생물학적 소스
vegetable oil
끓는 점
200 °C · >200°C
주요 응용
향료 및 향
화장품 원료 기능
향기피부 컨디셔닝 - 기타항산화제피부 컨디셔닝 - 밀폐제
InChI
InChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h19-22,29H,8-18H2,1-7H3

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 3건

This chemical does not meet GHS hazard criteria for 100% (121 of 121) of all reports.

Not Classified

Aggregated GHS information provided per 121 reports by companies from 1 notifications to the ECHA C&L Inventory.

유해성 정보

Regulatory Information · 3건

Regulation (EC) No 1333/2008 (amended)

Status: Active Update: 11-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/12703

Tocopherol: Does not have an individual approval but may be used under an appropriate group standard

EPA Safer ChemicalChemical: Tocopherols
Hazard Classes and CategoriesNot Classified

독성 정보

Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org

안전 데이터

wgk
1
Hazard Classifications
Skin Sens. 1
스토리지 클래스
10 - Combustible liquids

화학 및 산업

약리 정보

Protein BindingThere has not been described a specific plasma transport protein for tocopherol but it is thought that it is highly bound to lipoproteins such as VLDL, HDL and chylomicrons.
Pharmacodynamics · 1건

The antioxidant effects of tocopherol can be translated into different changes at the pharmacodynamic level. In vitro studies have shown that this antioxidant activity can produce modification in protein kinase C (PKC) which will later be translated into an inhibition of cell death. Some other derivate effects are the anti-inflammatory properties of tocopherol which can be related to the modulation of cytokines or prostaglandins, prostanoids and thromboxanes.

Mechanism of Action · 1건

Tocopherol acts as a radical scavenger. It mainly acts as an antioxidant for lipid bilayers. Tocopherol's functions depend on the H-atom donating ability, location, and movement within the membrane, as well as the efficiency in the radical recycling by some cytosolic reductants such as ascorbate. Tocopherol actions are related to the trap of radicals, and it has been shown that even in the absence of substituents in the ortho-positions, tocopherol can trap more than two radicals. The type of radicals available for tocopherol are alkyl and peroxy.

Biological Half-LifeThe elimination half-life ranged from 2.44 to 3.02 hours for δ-tocopherol, γ-tocopherol, and β-tocopherol.
Metabolism/Metabolites · 1건

Excess tocopherol is converted into their corresponding carboxyethylhydroxychroman (CEHC), based on the isomer of tocopherol. More deeply, the metabolism of tocopherol begins with the hepatic metabolism which is led by a CYP4F2/CYP3A4-dependent ω-hydroxylation of the side chains which leads to the formation of 13'-carboxychromanol. The metabolic pathway is followed by five cycles of β-oxidation. The β-oxidation cycles function by shortening the side chains, the first cycle results in the formation of carboxydimethyldecylhydroxychromanol followed by carboxymethyloctylhydroxychromanol. These two metabolites are categorized as long-chain metabolites and they are not excreted in the urine. Some intermediate-chain metabolites that are products of two rounds of β-oxidation are carboxymethylhexylhydroxychromanol and carboxymethylbutylhydroxychromanol. These intermediate-chain metabolites can be found in human feces and urine. The catabolic end-product of tocopherols, as stated before, is CEHC which can be largely found in urine and feces. Two new metabolites have been detected in human and mice feces. These new metabolites are 12'-hydroxychromanol and 11'-hydroxychromanol. Because of their chemistry, it is thought that these metabolites can be the evidence for a ω-1 and ω-2 hydroxylation which leads to an impaired oxidation of 12'-OH followed side-chain truncation.

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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
InChIKey
QUEDXNHFTDJVIY-UHFFFAOYSA-N
SMILES
C1(C)(CCCC(C)CCCC(C)CCCC(C)C)OC2=C(C=C(O)C(C)=C2C)CC1
LogP
10.724 · 10.724 (est)
EPA
Tocopherols (1406-66-2)
MeSH Pharmacological Classification · 2건

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.

Organic substances that are required in small amounts for maintenance and growth, but which cannot be manufactured by the human body.

Absorption, Distribution and Excretion · 4건

The absorption of tocopherol in the digestive tract requires the presence of fat. The bioavailability of tocopherols is highly dependent on the type of isomer that is administered where the alpha-tocopherol can present a bioavailability of 36%. This isomer specificity also determines the intestinal permeability in which the gamma-tocopherol presents a very low permeability. After oral administration, the Cmax was 1353.79 ng/ml for δ-tocopherol, 547.45 ng/ml for γ-tocopherol, 704.16 ng/ml for β-tocopherol, and 2754.36 ng/ml for α-tocopherol. The Tmax is three to four hours for δ-tocopherol, γ-tocopherol, and β-tocopherol and about six hours for α-tocopherol.

The pharmacokinetic profile of tocopherol indicates a longer time of excretion for tocopherols when compared to tocotrienols. The different conjugated metabolites are excreted in the urine or feces depending on the length of their side-chain. Due to their polarity, intermediate-chain metabolites and short-chain metabolites are excreted via urine as glucoside conjugates. A mixture of all the metabolites and precursors can be found in feces. The long-chain metabolites correspond to >60% of the total metabolites in feces. It is estimated that the fecal excretion accounts for even 80% of the administered dose.

The apparent volume of distribution was 0.284 ± 0.021 mL for δ-tocopherol, 0.799 ± 0.047 mL for γ-tocopherol, and 0.556 ± 0.046 mL for β-tocopherol.

Clearance ranged from 0.081 to 0.190 L/h for δ-tocopherol, γ-tocopherol, and β-tocopherol.

용도 및 제조

UsesCIR ingredient: Tocopherol
Household ProductsInformation on 270 consumer products that contain Tocopherol in the following categories is provided:
Use Classification · 3건

EPA Safer Chemical Functional Use Classes -> Preservatives and Antioxidants

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

Cosmetics -> Skin conditioning; Antioxidant

General Manufacturing Information2H-1-Benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-: ACTIVE

응용 분야

용도Tocopherols are a class or organic molecules. Many exhibit the activity of Vitamin E. They are commonly found in Olive and sunflower oils.

일반 설명Pale yellow, viscous liquid.

공급사57 곳

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