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430676

Sigma-Aldrich

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

97%

Sinónimos:

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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$72.01
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$266.95

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Precio de catálogo$75.80

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5 G
$72.01
25 G
$266.95

About This Item

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

$72.01

Precio de catálogo$75.80

Disponible para envío el02 de abril de 2025Detalles

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Ensayo

97%

Formulario

solid

mp

89-91 °C (lit.)

cadena 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

Clave InChI

SEBPXHSZHLFWRL-UHFFFAOYSA-N

Información sobre el gen

human ... AR(367)

Categorías relacionadas

Descripción general

2,2,5,7,8-Pentamethyl-6-chromanol has been reported as an vitamin E model compound.[1] It undergoes oxidation in presence of various alcohols, ranging from methanol to cholesterol, affords 5-alkoxymethyl-2,2,7,8-tetramethyl-6-chromanols.[2] Antioxidant moiety of vitamin E, 2,2,5,7,8-pentamethyl-6-chromanol (PMCol), is reported to have antiandrogen activity in prostate carcinoma cells.[3]

Aplicación

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.[1] 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.[4] It may be used as internal standard for the determination of α- and γ-tocopherol in the rabbit serum and liver by HPLC.[5]

Pictogramas

Exclamation mark
GHS07

Palabra de señalización

Warning

Frases de peligro

H315,H319,H335

Clasificaciones de peligro

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

Órganos de actuación

Respiratory system

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
MKCW4916
MKCG3306
MKBQ6112V
06904LH
01614HH

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Jolanta Gruszka et al.
Free radical biology & medicine, 45(6), 920-928 (2008-07-19)
Singlet oxygen quenching rate constants for tocopherol and tocotrienol homologues have been determined in organic solvents of different polarities, as well as for other biological prenyllipids such as plastoquinol, ubiquinol, and alpha-tocopherolquinol. The obtained results showed that the quenching activity
Katerina Krumova et al.
Journal of the American Chemical Society, 134(24), 10102-10113 (2012-05-10)
The preparation of two highly sensitive fluorogenic α-tocopherol (TOH) analogues which undergo >30-fold fluorescence intensity enhancement upon reaction with peroxyl radicals is reported. The probes consist of a chromanol moiety coupled to the meso position of a BODIPY fluorophore, where
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
Julien Chapelat et al.
Organic letters, 10(22), 5123-5126 (2008-10-22)
A diastereoselective synthesis of alpha-tocopherol 1 (93% de) was achieved via two key steps, (i) a highly diastereoselective Shi epoxidation of a trisubstituted alkene and (ii) an acid supported, "anti-Baldwin" epoxide ring opening under inversion of configuration leading to the
M H Kang et al.
The Journal of nutrition, 129(10), 1885-1890 (1999-09-28)
Plant glucosides possess antioxidative properties due to their ability to scavenge free radicals. Sesame seeds contain a class of these compounds, the sesaminol glucosides. To evaluate their antioxidative activity in vivo, we fed rabbits diets containing 1% cholesterol (Chol) with
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