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227811

Sigma-Aldrich

2-Phenylhydroquinone

97%

Synonym(s):

2,5-Biphenyldiol, 2,5-Dihydroxybiphenyl

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About This Item

Linear Formula:
C6H5C6H3(OH)2
CAS Number:
Molecular Weight:
186.21
Beilstein/REAXYS Number:
1949429
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

mp

98-100 °C (lit.)

functional group

phenyl

SMILES string

Oc1ccc(O)c(c1)-c2ccccc2

InChI

1S/C12H10O2/c13-10-6-7-12(14)11(8-10)9-4-2-1-3-5-9/h1-8,13-14H

InChI key

XCZKKZXWDBOGPA-UHFFFAOYSA-N

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pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - 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


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K Ushiyama et al.
Carcinogenesis, 13(8), 1469-1473 (1992-08-01)
[U-14C]o-Phenylphenol (OPP) was found to bind covalently to calf thymus DNA during a 60 min incubation in the presence of microsomes, but not in their absence, indicating that metabolic conversion of the parent compound, OPP, to an activated form is
Y Nakagawa et al.
Cancer letters, 101(2), 227-232 (1996-03-29)
The induction of 8-hydroxy-2'-deoxyguanosine (8-OHdG), an index of oxidative DNA modification, was investigated in CHO-K1 cells exposed to phenyl-hydroquinone (PHQ), a major metabolite of ortho-phenylphenol (OPP), an antimicrobial. Addition of PHQ at a concentration of 50 microM to CHO cell
David Brusick
Environmental and molecular mutagenesis, 45(5), 460-481 (2005-02-17)
Ortho-phenylphenol (OPP) and its sodium salt (SOPP) are commercial products that have wide human exposure and have been shown in several studies to be rodent carcinogens. Genetic toxicology data were assessed in an attempt to understand the carcinogenic mode of
Ayumi Yamamoto et al.
The FEBS journal, 275(22), 5733-5744 (2008-10-31)
Recently, we have shown that phenyl hydroquinone, a hepatic metabolite of the Ames test-negative carcinogen o-phenylphenol, efficiently induced aneuploidy in Saccharomyces cerevisiae. We further found that phenyl hydroquinone arrested the cell cycle at G(1) and G(2)/M. In this study, we
Kuniaki Tayama et al.
Pigment cell research, 15(6), 447-453 (2002-11-28)
The effects of o-phenylphenol (OPP) and its metabolite, phenylhydroquinone (PHQ) on the skin of JY-4 black guinea-pigs were studied. Topical application of 1 or 5% PHQ on the black skin of the back caused marked depigmentation and hypopigmentation of the

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