| Identification | More | [Name]
PHENYLGLYOXAL MONOHYDRATE | [CAS]
1075-06-5 | [Synonyms]
2,2-DIHYDROXY-1-PHENYL-ETHANONE
BENZOYLFORMALDEHYDE MONOHYDRATE
PHENYLGLYOXAL
PHENYLGLYOXAL HYDRATE
PHENYLGLYOXAL MONOHYDRATE
P-PHENYLGLYOXAL MONOHYDRATE
2,2-dihydroxy-1-phenyl-ethanon
2,2-dihydroxy-acetophenon
2,2-dihydroxyacetophenone | [EINECS(EC#)]
214-036-1 | [Molecular Formula]
C8H8O3 | [MDL Number]
MFCD00149499 | [Molecular Weight]
152.15 | [MOL File]
1075-06-5.mol |
| Chemical Properties | Back Directory | [Melting point ]
76-79 °C(lit.) | [Boiling point ]
142 °C125 mm Hg(lit.) | [density ]
1.1603 (rough estimate) | [refractive index ]
1.5120 (estimate) | [Fp ]
142°C/125mm | [storage temp. ]
2-8°C | [solubility ]
95% ethanol: soluble5%, clear to very slightly hazy, colorless to light yellow | [form ]
Powder | [pka]
10.97±0.41(Predicted) | [color ]
White to light yellow or pinkish | [Water Solubility ]
Partly miscible with water. | [BRN ]
1854721 | [InChI]
1S/C8H6O2.H2O/c9-6-8(10)7-4-2-1-3-5-7;/h1-6H;1H2 | [InChIKey]
YQBLQKZERMAVDO-UHFFFAOYSA-N | [SMILES]
[H]O[H].[H]C(=O)C(=O)c1ccccc1 | [CAS DataBase Reference]
1075-06-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302-H315-H319-H335 | [Precautionary statements ]
P301+P312+P330-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
MD3260000
| [HS Code ]
2914.40.4000 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 | [Toxicity]
mouse,LD50,oral,500mg/kg (500mg/kg),Journal of Medicinal and Pharmaceutical Chemistry. Vol. 1, Pg. 365, 1959. |
| Hazard Information | Back Directory | [Uses]
Phenylglyoxal monohydrate was used to modify pig muscle carbonic anhydraseIII and as a specific reagent for arginine groups. It was also used to prepare pyrrolinone and furan derivatives and as as a 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. | [Synthesis]
GENERAL METHOD: Selenium dioxide (220 mg, 2 mmol) was dissolved in a mixed solution of 1,4-dioxane (1 mL) and deionized water (2 drops), followed by the addition of acetophenone 1a (120 mg, 1 mmol). The reaction mixture was refluxed with stirring for 7 h (the reaction progress was monitored by TLC, the unfolding agent was ethyl acetate/petroleum ether, 1:4, v/v). After completion of the reaction, it was cooled to room temperature, dichloromethane (5 mL) was added to the mixture and filtered through diatomaceous earth. The diatomaceous earth was washed with dichloromethane (3 x 5 mL). All organic phases were combined and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with the eluent ethyl acetate/petroleum ether (1:10 v/v) to give benzoylformaldehyde hydrate 2a (121 mg, 80% yield). Compounds 2b~2m were synthesized following the same procedure in a range of 61%~82% yield. | [storage]
Store at -20°C | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 8, p. 1660 - 1664
[2] Tetrahedron Asymmetry, 2010, vol. 21, # 18, p. 2244 - 2248
[3] Tetrahedron, 2011, vol. 67, # 41, p. 8000 - 8008
[4] Chemistry of Heterocyclic Compounds, 2018, vol. 54, # 1, p. 51 - 57
[5] Khim. Geterotsikl. Soedin., 2018, vol. 54, # 1, p. 51 - 57,7 |
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