Phenylglyoxal monohydrate

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H8O3
Molecular Weight	152.1476
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(O)C(=O)C1=CC=CC=C1

InChI

InChIKey=NBIBDIKAOBCFJN-UHFFFAOYSA-N

InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,8,10-11H

HIDE SMILES / InChI

Molecular Formula	C8H8O3
Molecular Weight	152.1476
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Synthesis, spectroscopic and thermal studies of transition metal complexes derived from benzil and diethylenetriamine.	2007-10	17368084
Photoinitiation chemistry affects light transmission and degree of conversion of curing experimental dental resin composites.	2007-07	16914191
Analysis of the inhibition of mammalian carboxylesterases by novel fluorobenzoins and fluorobenzils.	2007-06-01	17399985
Lipid composition greatly affects the in vitro surface activity of lung surfactant protein mimics.	2007-05-15	17287113
Facile determination of DNA-binding nuclear factor-kappaB by chemiluminescence detection.	2007-05-01	17374353
Benzil-tethered precipitons for controlling solubility: a round-trip energy-transfer mechanism in the isomerization of extended stilbene analogues.	2007-04-04	17348650
Simultaneous fitting of X-ray and neutron diffuse scattering data.	2007-01	17179604
Trypanothione-dependent glyoxalase I in Trypanosoma cruzi.	2006-12-01	16958620
The role of charged residues in the transmembrane helices of monocarboxylate transporter 1 and its ancillary protein basigin in determining plasma membrane expression and catalytic activity.	2006-11-28	17127621
Binding of polyaminocarboxylate chelators to the active-site copper inhibits the GSNO-reductase activity but not the superoxide dismutase activity of Cu,Zn-superoxide dismutase.	2006-10-24	17042490
Intracellular inhibition of carboxylesterases by benzil: modulation of CPT-11 cytotoxicity.	2006-09	16985062
Monitoring of 8-oxo-7,8-dihydro-2'-deoxyguanosine in urine by high-performance liquid chromatography after pre-column derivatization with glyoxal reagents.	2006-08	16389633
Non-enzymatic model glycation reactions--a comprehensive study of the reactivity of a modified arginine with aldehydic and diketonic dicarbonyl compounds by electrospray mass spectrometry.	2006-06	16646000
The functional role of arginine 901 at the C-terminus of the human anion transporter band 3 protein.	2006-05	16751598
Citrate transporters play a critical role in aluminium-stimulated citrate efflux in rice bean (Vigna umbellata) roots.	2006-04	16446286
Reduction of activated carbonyl groups by alkyl phosphines: formation of alpha-hydroxy esters and ketones.	2006-03-21	16518496
Reactions of a modified lysine with aldehydic and diketonic dicarbonyl compounds: an electrospray mass spectrometry structure/activity study.	2006-02	16421861
Antimelanoma activity of apoptogenic carbonyl scavengers.	2006-02	16210394
Chemical modification studies of tryptophan, arginine and lysine residues in maize chloroplast ferredoxin:sulfite oxidoreductase.	2005-12	16307304
Structural insights into drug processing by human carboxylesterase 1: tamoxifen, mevastatin, and inhibition by benzil.	2005-09-09	16081098
Methylphenidate analogs with behavioral differences interact differently with arginine residues on the dopamine transporter in rat striatum.	2005-09-01	15945061
Inhibition of carboxylesterases by benzil (diphenylethane-1,2-dione) and heterocyclic analogues is dependent upon the aromaticity of the ring and the flexibility of the dione moiety.	2005-08-25	16107154
Purification and characterization of a serine alkaline protease from Bacillus clausii GMBAE 42.	2005-08	15988584
Chemical modification studies on alkaline phosphatase from pearl oyster (Pinctada fucata): a substrate reaction course analysis and involvement of essential arginine and lysine residues at the active site.	2005-07	15833276
The effect of camphorquinone (CQ) and CQ-related photosensitizers on the generation of reactive oxygen species and the production of oxidative DNA damage.	2005-07	15664636
The dimethyldioxirane-mediated oxidation of phenylethyne.	2005-06-21	16010366
Mutational analysis of the active-site residues crucial for catalytic activity of adenosine kinase from Leishmania donovani.	2005-05-01	15606359
Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases.	2005-04-21	15828829
Modification of permeability transition pore arginine(s) by phenylglyoxal derivatives in isolated mitochondria and mammalian cells. Structure-function relationship of arginine ligands.	2005-04-01	15671016
QM/MM studies of the enzyme-catalyzed dechlorination of 4-chlorobenzoyl-CoA provide insight into reaction energetics.	2004-10-27	15493922
Evidence for the involvement of arginyl residue at the active site of penicillin G acylase from Kluyvera citrophila.	2004-10	15604805
The role of carboxyl, guanidine and imidazole groups in catalysis by a midgut trehalase purified from an insect larvae.	2004-10	15475303
Chemical modification of arginine residues of Notechis scutatus scutatus notexin.	2004-10	15450923
Observation of the two triplet state conformations of alkyl phenylglyoxylates.	2004-09	15346192
Peptide-derivatized shell-cross-linked nanoparticles. 1. Synthesis and characterization.	2004-07-22	15264856
Covalent and noncovalent chemical modifications of arginine residues decrease dopamine transporter activity.	2004-06-15	15103693
Identification of arginine residues important for the activity of Escherichia coli signal peptidase I.	2004-05	15195997
Hydrogen-mediated C-C bond formation: catalytic regio- and stereoselective reductive condensation of alpha-keto aldehydes and 1,3-enynes.	2004-04-14	15070383
Identification and characterization of the pseudopterosin diterpene cyclase, elisabethatriene synthase, from the marine gorgonian, Pseudopterogorgia elisabethae.	2004-04-01	15019841
Kinetics of chemical modification of arginine residues in mitochondrial creatine kinase from bovine heart: evidence for negative cooperativity.	2004-04	15170384
A benzil and isoflavone derivatives from Derris scandens Benth.	2004-04	15110702
Complex formation between ferredoxin and Synechococcus ferredoxin: nitrate oxidoreductase.	2004-02-15	14871493
A diffuse reflectance comparative study of benzil inclusion within microcrystalline cellulose and beta-cyclodextrin.	2004-02	14872233
Overexpression and enzymatic characterization of Neisseria gonorrhoeae penicillin-binding protein 4.	2004-01	14686916
Asymmetric reduction of benzil to (S)-benzoin with whole cells of Bacillus cereus.	2003-12	14665737
The role of residues R97 and Y331 in modulating the pH optimum of an insect beta-glycosidase of family 1.	2003-12	14653813
Chloride channels in basolateral TAL membranes. XVIII. Phenylglyoxal induces functional mcCIC-Ka activity in basolateral MTAL membranes.	2003-09-15	14692446
The strength of dehalogenase-substrate hydrogen bonding correlates with the rate of Meisenheimer intermediate formation.	2003-08-12	12899635
Fungal phyA gene expressed in potato leaves produces active and stable phytase.	2003-06-27	12804608
Chemical modifications of alpha1,6-fucosyltransferase define amino acid residues of catalytic importance.	2003-05-29	12770769

Patents

Substance Class	Chemical Created by `admin` on `Wed Apr 02 19:47:53 GMT 2025` Edited by `admin` on `Wed Apr 02 19:47:53 GMT 2025`
Record UNII	6A8BDX43XD
Record Status	`FAILED`
Record Version

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Name

Type

Language

NSC-249825

Preferred Name

English

Phenylglyoxal monohydrate

Common Name

English

PHENYLGLYOXAL HYDRATE

Systematic Name

English

Benzeneacetaldehyde, ?-oxo-, monohydrate

Systematic Name

English

Glyoxal, phenyl-, hydrate

Common Name

English

Benzeneacetaldehyde, ?-oxo-, hydrate (1:1)

Systematic Name

English

2,2-Dihydroxy-1-phenylethan-1-one

Systematic Name

English

Code System Code Type Description

FDA UNII

6A8BDX43XD