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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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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

Quality Level

100

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)

Related Categories

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.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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