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T76503

Sigma-Aldrich

Trimethylhydroquinone

97%

Synonym(s):

1,4-Dihydroxy-2,3,5-trimethylbenzene, 3,6-Dihydroxypseudocumene

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About This Item

Linear Formula:
(CH3)3C6H-1,4-(OH)2
CAS Number:
700-13-0
Molecular Weight:
152.19
Beilstein:
1909183
EC Number:
211-838-3
MDL number:
MFCD00002346
UNSPSC Code:
12352100
PubChem Substance ID:
24900467
NACRES:
NA.22

Quality Level

100

Assay

97%

mp

169-172 °C (lit.)

SMILES string

Cc1cc(O)c(C)c(C)c1O

InChI

1S/C9H12O2/c1-5-4-8(10)6(2)7(3)9(5)11/h4,10-11H,1-3H3

InChI key

AUFZRCJENRSRLY-UHFFFAOYSA-N

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Application

Trimethylhydroquinone is a key precursor for the synthesis of tocopherols (vitamin E) and (±)-madindolines.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Inhalation - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

375.8 °F - closed cup

Flash Point(C)

191 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Enantioselective Palladium-Catalyzed Total Synthesis of Vitamin E by Employing a Domino Wacker-Heck Reaction.
Tietze, Lutz F et al.
Chemistry?A European Journal , 12(34), 8770-8776 (2006)
Vitaly A Roginsky et al.
Aging, 1(5), 481-489 (2010-03-03)
The chain-breaking antioxidant activities of reduced form of novel type of geroprotectors, mitochondria-targeted quinones (QH(2)) have quantitatively been measured for the first time. To this end, the chain peroxidation of methyl linoleate (ML) in Triton micelles was used as a
Synthesis of (?)-madindolines and chemical models. Studies of chemical reactivity.
McComas, Casey C et al.
Organic Letters, 4(14), 2337-2340 (2002)
P R Rich
Biochimica et biophysica acta, 722(2), 271-280 (1983-02-17)
(1) A kinetic analysis of electron donation into and through the cytochrome b-c1 complex isolated from bovine heart mitochondria has been undertaken, using trimethoquinol as the donor. (2) Rate constants of two routes of redox equilibration with quinols have been
S Schmidt et al.
Biochimica et biophysica acta, 1568(1), 83-89 (2001-12-04)
The dioxygenolytic catabolism of five C-methylated hydroquinones and 2,6-dichlorohydroquinone in Pseudomonas sp. strain HH35 was elucidated. This organism, which is known to catabolise 2,6-dimethylhydroquinone by 1,2-cleavage, accumulated metabolites from 2-methyl-, 2,3-dimethyl-, 2,5-dimethyl-, 2,3,5-trimethyl- and 2,3,5,6-tetramethylhydroquinone which we isolated and characterised
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