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Clovamide

Names

[ CAS No. ]:
53755-02-5

[ Name ]:
Clovamide

[Synonym ]:
clovamide
(-)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-3-hydroxy-L-tyrosine
3-(3,4-dihydroxy-phenyl)-(S)-2-[3-trans-(3,4-dihydroxy-phenyl)-acryloylamino]-propionic acid
L-Tyrosine, N-[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]-3-hydroxy-
N-[(2E)-3-(3,4-Dihydroxyphenyl)-2-propenoyl]-3-hydroxy-L-tyrosine
N-(3',4'-DIHYDROXY-(E)-CINNAMOYL)-3-HYDROXY-L-TYROSINE
N-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-3-hydroxy-L-tyrosine
caffeoyl L-DOPA

Biological Activity

[Description]:

Clovamide (trans-Clovamide), a natural phenolic compound, is a potent antioxidant. Clovamide is an excellent ROS and oxygen radical scavenger. Clovamide also has anti-inflammatory and neuroprotective effects[1][2]. Clovamide is an anti-microbial with activity against the human pathogens influenza A subtype H5N1, Trypanosoma evansi, and Heliobacter pylori[3].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Influenza Virus
Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Inflammation/Immunology
Research Areas >> Neurological Disease
Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

Clovamide is able to protect neurons from injury in three in vitro models of neuronal death: oxidative stress, excitotoxicity and OGD/reoxygenation. In SH-SY5Y human neuroblastoma cells, Clovamide (10-100 µM) significantly protects cell death, with an EC50 value of 3.6 µM. Clovamide also significantly enhances PPARγ expression[2]. Clovamide inhibits growth of three pathogens of cacao in the genus Phytophthora, is a substrate for cacao polyphenol oxidase, and is a contributor to enzymatic browning. Clovamide inhibiteds proteinase and pectinase in vitro[3].

[References]

[1]. Naike Ye, et al. Antioxidant studies by hydrodynamic voltammetry and DFT, quantitative analyses by HPLC-DAD of clovamide, a natural phenolic compound found in Theobroma Cacao L. beans. Food Chem. 2021 Mar 30;341(Pt 2):128260.

[2]. S Fallarini, et al. Clovamide and rosmarinic acid induce neuroprotective effects in in vitro models of neuronal death. Br J Pharmacol. 2009 Jul;157(6):1072-84.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
777.0±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C18H17NO7

[ Molecular Weight ]:
359.33

[ Flash Point ]:
423.7±32.9 °C

[ Exact Mass ]:
359.100494

[ PSA ]:
147.32000

[ LogP ]:
0.84

[ Vapour Pressure ]:
0.0±2.8 mmHg at 25°C

[ Index of Refraction ]:
1.723

Related Compounds