430676
2,2,5,7,8-Pentamethyl-6-chromanol
97%
Synonym(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
Empirical Formula (Hill Notation):
C14H20O2
CAS Number:
Molecular Weight:
220.31
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Assay:
97%
Form:
solid
General description
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.
Application
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Alexey G Kruglov et al.
Biochemical pharmacology, 74(4), 545-556 (2007-06-26)
The role of NAD(P)H-dependent oxidoreductases of the outer mitochondrial membrane (OMM) in the activation of lipophilic cationic dyes is poorly understood. In the present study we compared the rates of production of reactive oxygen species (ROS) and mitochondriotoxic effects of
C K Van Pelt et al.
Analytical chemistry, 70(20), 4369-4375 (1998-10-31)
A rapid, high-selectivity method with subfemtomole sensitivity is reported for quantification of alpha-tocopherol in plasma-based gas chromatography/tandem mass spectrometry (GC/MS/MS) using a tabletop quadrupole ion trap mass spectrometer. Sample workup is rapid, consisting of protein precipitation followed by liquid/liquid extraction
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
New oxidation products of 2, 2, 5, 7, 8-pentamethyl-6-chromanol.
Suarna C, et al.
Lipids, 23(12), 1129-1131 (1988)
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
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