Propiophenone, 3,4'-dihydroxy-3'-methoxy-

Names

[ Name ]:
Propiophenone, 3,4'-dihydroxy-3'-methoxy-

[Synonym ]:
Propiophenone,3,4'-dihydroxy-3'-methoxy
3-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
1-Propanone, 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-
Propiophenone, 3,4'-dihydroxy-3'-methoxy-

Biological Activity

[Description]:

β-Hydroxypropiovanillone, a natural compound, shows significant concentration-dependent inhibitory effects on α-glucosidase with an IC50 of 257.8 μg/mL[1].

[Related Catalog]:

Research Areas >> Cardiovascular Disease

[Target]

IC50: 257.8 μg/mL (α-glucosidase)[1]

[In Vitro]

β-hydroxypropiovanillone and its analogs can be obtained by chemoselective catalytic oxidation of lignin using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone/tert-butyl nitrite/O2, followed by cleavage of arylglycerol-β-aryl ether with zinc[2]. In SYK-6 cells, β-hydroxypropiovanillone (HPV) is oxidized to vanilloyl acetic acid (VAA) via vanilloyl acetaldehyde (VAL). The resulting VAA was further converted into vanillate through the activation of VAA by coenzyme A[3].

[References]

[1]. Lv Q , et al. Dihydrochalcone-derived polyphenols from tea crab apple (Malus hupehensis) and their inhibitory effects on α-glucosidase in vitro. Food Funct. 2019;10(5):2881-2887.

[2]. Higuchi Y, et al. Bacterial Catabolism of β-Hydroxypropiovanillone and β-Hydroxypropiosyringone Produced in the Reductive Cleavage of Arylglycerol-β-Aryl Ether in Lignin. Appl Environ Microbiol. 2018;84(7):e02670-17. Published 2018 Mar 19.

[3]. Higuchi Y, et al. Discovery of novel enzyme genes involved in the conversion of an arylglycerol-β-aryl ether metabolite and their use in generating a metabolic pathway for lignin valorization. Metab Eng. 2019;55:258-267.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
408.2±35.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₀H₁₂O₄

[ Molecular Weight ]:
196.200

[ Flash Point ]:
165.4±19.4 °C

[ Exact Mass ]:
196.073563

[ PSA ]:
66.76000

[ LogP ]:
0.69

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

[ Index of Refraction ]:
1.561

Safety Information

[ Hazard Codes ]:
Xi

[ HS Code ]:
2914509090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914509090

[ Summary ]:
HS:2914509090 other ketones with other oxygen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%