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173401

Sigma-Aldrich

1,2,4-Benzenetriol

ReagentPlus®, 99%

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Synonym(s):
Hydroxyhydroquinone
Linear Formula:
C6H3(OH)3
CAS Number:
Molecular Weight:
126.11
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.23

product line

ReagentPlus®

Assay

99%

form

solid

mp

140 °C (subl.) (lit.)

SMILES string

Oc1ccc(O)c(O)c1

InChI

1S/C6H6O3/c7-4-1-2-5(8)6(9)3-4/h1-3,7-9H

InChI key

GGNQRNBDZQJCCN-UHFFFAOYSA-N

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General description

1,2,4-Benzenetriol is also known as hydroxyhydroquinone. It is an intermediary metabolite of benzene that is present in roasted coffee beans. It is mutagenic and it causes cleaving of DNA single strands by the generation of reactive oxygen species.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - 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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Generation of hydrogen peroxide from hydroxyhydroquinone and its inhibition by superoxide dismutase
Hiramoto K, et al.
Journal of Oleo Science, 50(1), 21-28 (2001)
DNA breakage induced by 1, 2, 4-benzenetriol: relative contributions of oxygen-derived active species and transition metal ions
Li AS, et al.
Free Radical Biology & Medicine, 30(9), 943-956 (2001)
Karolina Nordin et al.
Applied and environmental microbiology, 71(11), 6538-6544 (2005-11-05)
Arthrobacter chlorophenolicus A6, a previously described 4-chlorophenol-degrading strain, was found to degrade 4-chlorophenol via hydroxyquinol, which is a novel route for aerobic microbial degradation of this compound. In addition, 10 open reading frames exhibiting sequence similarity to genes encoding enzymes
Rolis Chien-Wei Hou et al.
Journal of biomedical science, 13(1), 89-99 (2005-11-26)
Hydroxyhydroquinone or 1,2,4-benzenetriol (BT) detected in the beverages has a structure that coincides with the water-soluble form of a sesame lignan, sesamol. We previously showed that sesame antioxidants had neuroprotective abilities due to their antioxidant properties and/or inducible nitric oxide
Ryuji Ochiai et al.
Hypertension research : official journal of the Japanese Society of Hypertension, 32(11), 969-974 (2009-08-29)
Recent studies suggest that chlorogenic acids, which are the main components of the polyphenol class in coffee, decrease blood pressure, and that hydroxyhydroquinone (HHQ), which is generated by roasting coffee beans, inhibits the antihypertensive effect of chlorogenic acids in brewed

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