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142433

Sigma-Aldrich

Phenylglyoxal hydrate

97%

Sinónimos:

2,2-Dihydroxyacetophenone

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About This Item

Fórmula lineal:
C6H5COCHO · xH2O
Número de CAS:
1075-06-5
Peso molecular:
134.13 (anhydrous basis)
EC Number:
214-036-1
MDL number:
MFCD00149499
UNSPSC Code:
12352100
PubChem Substance ID:
24848526
NACRES:
NA.22

Quality Level

200

assay

97%

form

powder

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

SMILES string

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

InChI

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

InChI key

YQBLQKZERMAVDO-UHFFFAOYSA-N

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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_germany

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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Certificados de análisis (COA)

Lot/Batch Number
STBK2402
STBJ9208
STBH3377
STBG3435V
STBF7407V

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Analytica Chimica Acta, 278, 275-275 (1993)
Analytica Chimica Acta, 287, 75-75 (1994)
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
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
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