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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/REAXYS Number:
1909183
EC Number:
211-838-3
MDL number:
MFCD00002346
UNSPSC Code:
12352100
PubChem Substance ID:
24900467
NACRES:
NA.22

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.

signalword

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

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

375.8 °F - closed cup

flash_point_c

191 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Faceshields, 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)
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
Synthesis of (?)-madindolines and chemical models. Studies of chemical reactivity.
McComas, Casey C et al.
Organic Letters, 4(14), 2337-2340 (2002)
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
U Burner et al.
Redox report : communications in free radical research, 5(4), 185-190 (2000-09-20)
Myeloperoxidase is very susceptible to reducing radicals because the reduction potential of the ferric/ferrous redox couple is much higher compared with other peroxidases. Semiquinone radicals are known to reduce heme proteins. Therefore, the kinetics and spectra of the reactions of
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