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430676

Sigma-Aldrich

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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₪1,391.00

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5 G
₪390.00
25 G
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About This Item

Empirical Formula (Hill Notation):
C14H20O2
CAS Number:
950-99-2
Molecular Weight:
220.31
MDL number:
MFCD00210347
UNSPSC Code:
12352100
PubChem Substance ID:
24866935
NACRES:
NA.22

₪390.00

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Assay

97%

form

solid

mp

89-91 °C (lit.)

SMILES string

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

InChI key

SEBPXHSZHLFWRL-UHFFFAOYSA-N

Gene Information

human ... AR(367)

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General description

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]

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.[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]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW4916
MKCG3306
MKBQ6112V
06904LH
01614HH

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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
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
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
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
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