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430676

Sigma-Aldrich

2,2,5,7,8-Pentamethyl-6-chromanol

97%

Sinônimo(s):

α-C-1-Chromanol, 2,2,5,7,8-Pentamethyl-3,4-dihydrochromen-6-ol, 2,2,5,7,8-Pentamethyl-6-hydroxychroman, 3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol, 6-Hydroxy-2,2,5,7,8-pentamethylchroman

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About This Item

Fórmula empírica (Notação de Hill):
C14H20O2
Número CAS:
950-99-2
Peso molecular:
220.31
Número MDL:
MFCD00210347
Código UNSPSC:
12352100
ID de substância PubChem:
24866935
NACRES:
NA.22

Nível de qualidade

100

Ensaio

97%

forma

solid

pf

89-91 °C (lit.)

cadeia de caracteres SMILES

Cc1c(C)c2OC(C)(C)CCc2c(C)c1O

InChI

1S/C14H20O2/c1-8-9(2)13-11(10(3)12(8)15)6-7-14(4,5)16-13/h15H,6-7H2,1-5H3

chave InChI

SEBPXHSZHLFWRL-UHFFFAOYSA-N

Informações sobre genes

human ... AR(367)

Categorias relacionadas

Descrição geral

2,2,5,7,8-Pentamethyl-6-chromanol has been reported as an vitamin E model compound. It undergoes oxidation in presence of various alcohols, ranging from methanol to cholesterol, affords 5-alkoxymethyl-2,2,7,8-tetramethyl-6-chromanols. Antioxidant moiety of vitamin E, 2,2,5,7,8-pentamethyl-6-chromanol (PMCol), is reported to have antiandrogen activity in prostate carcinoma cells.

Aplicação

2,2,5,7,8-Pentamethyl-6-chromanol is the suitable reagent used for the quantitative analysis of α-tocopherol by plasma-based gas chromatography/tandem mass spectrometry (GC/MS/MS) using a tabletop quadrupole ion trap mass spectrometer. It may be employed as α-tocopherol model compound and on oxidation by t-butyl hydroperoxide in chloroform, in the presence of alcohol, affords 5-alkoxymethyl-2,2,7,8-tetramethyl-6-chromanol. It may be used as internal standard for the determination of α- and γ-tocopherol in the rabbit serum and liver by HPLC.

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H315,H319,H335

Classificações de perigo

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análise (COA)

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Qing Jiang et al.
Proceedings of the National Academy of Sciences of the United States of America, 105(51), 20464-20469 (2008-12-17)
Cyclooxygenase (COX-1/COX-2)-catalyzed eicosanoid formation plays a key role in inflammation-associated diseases. Natural forms of vitamin E are recently shown to be metabolized to long-chain carboxychromanols and their sulfated counterparts. Here we find that vitamin E forms differentially inhibit COX-2-catalyzed prostaglandin
Urs Hengartner et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(4), 1306-1311 (2009-12-17)
Alpha-tocopherol was synthesized from a chiral intermediate alpha-hydroxy ester by means of two ring-closing methods to yield the chromanol in 94% diastereomeric excess.
C Suarna et al.
Lipids, 24(1), 56-60 (1989-01-01)
The vitamin E model compound, 2,2,5,7,8-pentamethyl-6-chromanol, has been oxidized with t-butyl hydroperoxide in chloroform in order to simulate in vivo oxidations due to lipid hydroperoxides. In the presence of a variety of alcohols, ranging from methanol to cholesterol, the corresponding
New oxidation products of 2, 2, 5, 7, 8-pentamethyl-6-chromanol.
Suarna C, et al.
Lipids, 23(12), 1129-1131 (1988)
Todd A Thompson et al.
Molecular cancer therapeutics, 2(8), 797-803 (2003-08-27)
Antioxidants, such as vitamin E, are being investigated for efficacy in prostate cancer prevention. In this study, we show that the antioxidant moiety of vitamin E, 2,2,5,7,8-pentamethyl-6-chromanol (PMCol), has antiandrogen activity in prostate carcinoma cells. In the presence of PMCol
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