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173401

Sigma-Aldrich

1,2,4-Benzenetriol

ReagentPlus®, 99%

Synonym(s):

Hydroxyhydroquinone

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About This Item

Linear Formula:
C6H3(OH)3
CAS Number:
533-73-3
Molecular Weight:
126.11
EC Number:
208-575-1
MDL number:
MFCD00002198
UNSPSC Code:
12162002
PubChem Substance ID:
24850442
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
GHS05,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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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)
Zbigniew Srokol et al.
Carbohydrate research, 339(10), 1717-1726 (2004-06-29)
During the hydrothermal upgrading of biomass, hydrolysis to glucose is an important step. To elucidate some of the reaction pathways that follow this initial hydrolysis, the hydrothermal treatment (340 degrees C, 27.5 MPa, 25-204 s) of dilute (50 mM) solutions
Atsushi Suzuki et al.
American journal of hypertension, 20(5), 508-513 (2007-05-09)
Ferulic acid (FA), a phytochemical constituent, has antihypertensive effects, but a detailed understanding of its effects on vascular function remains unclear. The vasoreactivity of FA was assessed using aortic rings isolated from normotensive Wistar Kyoto (WKY) and spontaneously hypertensive rats
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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