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Merck
CN

142433

Phenylglyoxal hydrate

97%

Synonym(s):

2,2-Dihydroxyacetophenone

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About This Item

Linear Formula:
C6H5COCHO · xH2O
CAS Number:
1075-06-5
Molecular Weight:
134.13 (anhydrous basis)
NACRES:
NA.22
PubChem Substance ID:
24848526
UNSPSC Code:
12352100
EC Number:
214-036-1
MDL number:
MFCD00149499
Assay:
97%
Form:
powder

Key Documents

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assay

97%

form

powder

InChI key

YQBLQKZERMAVDO-UHFFFAOYSA-N

InChI

1S/C8H6O2.H2O/c9-6-8(10)7-4-2-1-3-5-7;/h1-6H;1H2

SMILES string

[H]O[H].[H]C(=O)C(=O)c1ccccc1

bp

142 °C/125 mmHg (lit.)

mp

76-79 °C (lit.)

solubility

95% ethanol: soluble 5%, clear to very slightly hazy, colorless to light yellow

functional group

aldehyde, ketone, phenyl

Quality Level

200

Related Categories

Application

Phenylglyoxal hydrate was used :
  • to modify pig muscle carbonic anhydraseIII
  • as specific reagent for arginine groups
  • to prepare pyrrolinone and furan derivatives
  • as chemiluminescent reagent for the determination of purines

Biochem/physiol Actions

Phenylglyoxal is a potent inhibitor of mitochondrial aldehyde dehydrogenase. It reacts with arginine residues in purified Hageman factor (HF, Factor XII) and causes inhibition of its coagulant properties.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000518868
0000518868
0000421998
0000409542
0000409542

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Analytica Chimica Acta, 278, 275-275 (1993)
L M Pullan et al.
Biochemistry, 24(3), 635-640 (1985-01-29)
Mammalian carbonic anhydrase III has previously been shown to catalyze the hydrolysis of p-nitrophenyl phosphate in addition to possessing the conventional CO2 hydratase and p-nitrophenylacetate esterase activities. Modification of pig muscle carbonic anhydrase III with the arginine reagent phenylglyoxal yielded
O D Radnoff et al.
Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.), 148(1), 177-182 (1975-01-01)
Exposure of purified Hageman factor (HF, Factor XII) to phenylglyoxal hydrate (PHG), an agent reacting with arginine residues in protein, inhibited its coagulant properties upon subsequent exposure of negatively charged agents. Once HF had been exposed to kaolin or ellagic
William A Irwin et al.
Biochemical and biophysical research communications, 291(2), 215-219 (2002-02-16)
Fructose has been shown to protect hepatocyte viability during hypoxia or exposure to mitochondrial electron transport inhibitors. We report here that the fructose metabolite D-glyceraldehyde (D-GA) is a good inhibitor of the mitochondrial permeability transition pore (PTP) in isolated rat
Synthesis, 783-783 (1993)
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