3-(2,4-Dihydroxyphenyl)propionic acid

Names

[ Name ]:
3-(2,4-Dihydroxyphenyl)propionic acid

[Synonym ]:
3-(2,4-Dihydroxyphenyl)propanoic acid
Benzenepropanoic acid, 2,4-dihydroxy-
MFCD00143017

Biological Activity

[Description]:

3-(2,4-Dihydroxyphenyl)propanoic acid (DPPacid) is a potent and competitive tyrosinase inhibitor, inhibits L-Tyrosine and DL-DOPA with an IC50 and a Ki of 3.02 μM and 11.5 μM, respectively[1].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Metabolic Enzyme/Protease >> Tyrosinase

[Target]

Ki: 3.02 μM (L-Tyrosine); 11.5 μM (DL-DOPA)[1]

[References]

[1]. Shimizu K, et al. Novel vitamin E derivative with 4-substituted resorcinol moiety has both antioxidant and tyrosinase inhibitory properties. Lipids. 2001 Dec;36(12):1321-6.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
418.0±14.0 °C at 760 mmHg

[ Melting Point ]:
158-162ºC

[ Molecular Formula ]:
C₉H₁₀O₄

[ Molecular Weight ]:
182.173

[ Flash Point ]:
220.8±16.6 °C

[ Exact Mass ]:
182.057907

[ PSA ]:
77.76000

[ LogP ]:
0.38

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.620

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2918290000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2918290000

[ Summary ]:
HS: 2918290000 other carboxylic acids with phenol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) VAT:17.0% MFN tariff:6.5% General tariff:30.0%

Articles

The use of enzyme-coupled magnetic nanoparticles for studying the spectra of unusual substrates of mushroom tyrosinase by direct surface-assisted laser desorption/ionisation and high-resolution electrospray ionisation quadrupole-quadrupole-time-of-flight mass spectrometry.

Rapid Commun. Mass Spectrom. 28(18) , 1957-63, (2014)

Tyrosinase-coupled magnetic particles (EMPs) were used to demonstrate that resorcinol-containing tyrosinase inhibitors are oxidised by tyrosinase only in the presence of the enzyme's classic substrate...

The protein oxidation product 3,4-dihydroxyphenylalanine (DOPA) mediates oxidative DNA damage.

Biochem. J. 330 ( Pt 3) , 1059-67, (1998)

A major product of hydroxy-radical addition to tyrosine is 3, 4-dihydroxyphenylalanine (DOPA) which has reducing properties. Protein-bound DOPA (PB-DOPA) has been shown to be a major component of the ...

Phenoloxidase and QX disease resistance in Sydney rock oysters (Saccostrea glomerata).

Dev. Comp. Immunol. 28(6) , 565-9, (2004)

QX is a fatal disease in Sydney rock oysters (Saccostrea glomerata) that results from infection by the protistan parasite, Marteilia sydneyi. Since 1997, the New South Wales Fisheries Service has bred...