Skip to Content
MilliporeSigma
All Photos(1)

Documents

142433

Sigma-Aldrich

Phenylglyoxal hydrate

97%

Synonym(s):

2,2-Dihydroxyacetophenone

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
C6H5COCHO · xH2O
CAS Number:
1075-06-5
Molecular Weight:
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

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

Looking for similar products? Visit Product Comparison Guide

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

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - 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

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 2

1 of 2

Ethyl benzoylformate 95%

Sigma-Aldrich

258911

Ethyl benzoylformate

Pyruvaldehyde solution 40 wt. % in H2O

Sigma-Aldrich

W296902

Pyruvaldehyde solution

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
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
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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service