3,4-dihydroxyphenylpyruvic acid

3,4-dihydroxyphenylpyruvic acid Property

Melting point:

190-192℃ (decomposition)

Boiling point:

447.3±35.0 °C(Predicted)

Density 

1.540±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

2.42±0.54(Predicted)

Appearance

Light green to green Solid

InChI

InChI=1S/C9H8O5/c10-6-2-1-5(3-7(6)11)4-8(12)9(13)14/h1-3,10-11H,4H2,(H,13,14)

InChIKey

LQQFFJFGLSKYIR-UHFFFAOYSA-N

SMILES

C(O)(=O)C(CC1=CC=C(O)C(O)=C1)=O

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

3,4-dihydroxyphenylpyruvic acid Chemical Properties,Usage,Production

Definition

ChEBI: A 2-oxo monocarboxylic acid that is pyruvic acid in which one of the methyl hydrogens is substituted by a 3,4-dihydroxyphenyl group.

Synthesis

General procedure for the synthesis of 3-(3,4-dihydroxyphenyl)-2-oxopropanoic acid from 4-hydroxyphenylpyruvic acid: the reaction was carried out under homogeneous and non-homogeneous conditions in a CH2Cl2/buffer system. This was done as follows: phenol (0.05 mmol), tyrosinase (600 IU) and an appropriate amount of 0.1 M sodium phosphate buffer (pH 7, CH2Cl2/buffer volumetric ratio of about 1:0.1) were suspended in CH2Cl2 (2.5 mL) and preheated at 50 °C. Subsequently, the reaction system was transferred to a 25 °C environment with continuous stirring under O2 atmosphere for 24 hours. The reaction process was monitored by thin layer chromatography (TLC, unfolding agent was hexane/EtOAc=2.0:1.0). After complete conversion of the substrate, the immobilized enzyme was recovered by filtration, and the organic layer was separated and concentrated under reduced pressure. The crude product was solubilized with equal volumes of H2O and THF (2.0 mL), Na2S2O4 was added and stirred for 5 min. The reaction mixture was diluted with EtOAc (4.0 mL) and the aqueous phase was separated from the organic phase. The organic phase was dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude product was purified by fast column chromatography if necessary. The structure of the products was confirmed by 1H NMR, 13C NMR, GC-MS (after methylsilylation), and elemental analysis.The GC-MS analysis was done on a Shimadzu GC-MS QP5050 instrument with an SPB column (25 m×0.25 mm, film thickness 0.25 μm), and the initial temperature was maintained at 100 °C for 2 min, and the initial temperature was then increased to 2 μm at a rate of 10 °C/ The initial temperature of 100 °C was held for 2 min, and then the temperature was increased to 280 °C at a rate of 10 °C/min and held for 25 min. The inlet temperature was set at 280 °C. High purity helium was used as the carrier gas at a flow rate of 2.7 mL/min. The mass spectrometry acquisition was performed in 70 eV electron bombardment ionization mode. Dodecane was used as an internal standard for quantitative analysis. The MS data corresponded to fully methylsilylated derivatives except for compounds 3c and 3d.

References

[1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 24, p. 7699 - 7708