53755-02-5

Basic information

• Product Name: N-[3’,4’-Dihydroxy-(E)-cinnamoyl]-3-hydroxy-L-tyrosine
• Synonyms: N-[(2E)-3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]-3-hydroxy-L-tyrosine;N-[3’,4’-Dihydroxy-(E)-cinnamoyl]-3-hydroxy-L-tyrosine;trans-Clovamide;L-Tyrosine, N-[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]-3-hydroxy-
• CAS NO: 53755-02-5
• Molecular Formula: C₁₈H₁₇NO₇
• Molecular Weight: 359.33008
• Product Categories: Amino Acids & Derivatives;Aromatics
• Mol File: 53755-02-5.mol
• Article Data: 9

Chemical Properties

• Melting Point: 108-112°C
• Boiling Point: 777°C at 760 mmHg
• Flash Point: 423.7°C
• Appearance: /
• Density: 1.527g/cm³
• Vapor Pressure: 2.06E-25mmHg at 25°C
• Refractive Index: 1.722
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: N-[3’,4’-Dihydroxy-(E)-cinnamoyl]-3-hydroxy-L-tyrosine(CAS DataBase Reference)
• NIST Chemistry Reference: N-[3’,4’-Dihydroxy-(E)-cinnamoyl]-3-hydroxy-L-tyrosine(53755-02-5)
• EPA Substance Registry System: N-[3’,4’-Dihydroxy-(E)-cinnamoyl]-3-hydroxy-L-tyrosine(53755-02-5)

Safety Data

• Hazardous Substances Data: 53755-02-5(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Solid

Uses

Different sources of media describe the Uses of 53755-02-5 differently. You can refer to the following data:
1. It was identified in the antioxidant polyphenolic fraction of cocoa (Theobroma cacao L.). pound.
2. It was identified in the antioxidant polyphenolic fraction of cocoa (Theobroma cacao L.). As a naturally occurring caffeoyl conjugate, Clovamide represents an interesting antiradical/antioxidant compound.

InChI:InChI=1/C18H17NO7/c20-13-4-1-10(8-15(13)22)3-6-17(24)19-12(18(25)26)7-11-2-5-14(21)16(23)9-11/h1-6,8-9,12,20-23H,7H2,(H,19,24)(H,25,26)/b6-3+/t12-/m0/s1

Upstream product

• 59-92-7 levodopa 
• 1421-65-4 L-dopa methyl ester hydrochloride 
• 82592-68-5 (E)-3,4-di-O-acetylcaffeoyl chloride 
• 331-39-5 caffeic acid 
• 120094-83-9 (S)-3-(3,4-dihydroxyphenyl)-2-[3-(3,4-dihydroxyphenyl)acryloylamino]propionic acid methyl ester 
• 77201-71-9 (E)-3-(3,4-dihydroxyphenyl)acryloyl chloride 
• 88623-81-8 3,4-diacetoxycinnamic acid 

Downstream Products

• 64803-83-4 pentamethyl-trans-clovamide 

Relevant articles and documents

Induction of clovamide by jasmonic acid in red clover

The effect of jasmonic acid (JA) on the secondary metabolism of 5-day- old red clover seedlings was investigated. Induction of the formation of four compounds was found in roots after treatment with 50 μM JA for 48 h, while no induction was observed in the shoots. These compounds, whose formation was induced by JA addition, were isolated and identified as caffeoyl DOPA (clovamide), caffeoyltyrosine, p-coumaroyl DOPA and p-coumaroyltyrosine, by ion-spray MS and 1H NMR analyses, and by chemical synthesis. Among them, clovamide was the most abundant, while the other amides represented only a minor portion. Clovamide started to increase in amount 24-36 h after treatment and reached a maximum after 96 h (2.81 nmol/mg fr. wt.). The induction of their formation was observed even with 5 μM of JA, and the amount increased with concentrations up to 100 μM. Treatment with 1 mM CuCl2, which elicits accumulation of the phytoalexin maackiain in red clover, caused a decrease in clovamide amount. (C) 2000 Elsevier Science Ltd.

Structure-activity relationship of clovamide and its related compounds for the inhibition of amyloid β aggregation

Alzheimer's disease (AD), a neurodegenerative disorder, is characterized by aggregation of amyloid β-protein (Aβ). Aβ aggregates through β-sheet formation and induces cytotoxicity against neuronal cells. Inhibition of Aβ aggregation by naturally occurring compounds is thus a promising strategy for the treatment of AD. We have already reported that caffeoylquinic acids and phenylethanoid glycosides, which possess two or more catechol moieties, strongly inhibited Aβ aggregation. Clovamide (1) containing two catechol moieties, isolated from cacao beans (Theobroma cacao L.), is believed to exhibit preventive effects on Aβ aggregation. To investigate the structure-activity relationship of clovamide (1) for the inhibition of Aβ aggregation, we synthesized 1 and related compounds 2–11 through reaction between L-DOPA, D-DOPA, L-tyrosine, or L-phenylalanine and caffeic acid, p-coumaric acid, or cinnamic acid, and compounds 12 and 13 were derived from 1. Among tested compounds 1–13, those containing one or two catechol moieties exhibited potent anti-aggregation activity, whereas the non-catechol-type related compounds showed little or no activity. This suggests that at least one catechol moiety is essential for inhibition of Aβ42 aggregation, and this activity increases depending on the number of catechol moieties. Consequently, clovamide (1) and its related compounds may be a promising therapeutic option for inhibiting Aβ-mediated pathology in AD.

Caffeoylglycolic and caffeoylamino acid derivatives, halfmers of l-chicoric acid, as new HIV-1 integrase inhibitors

Human immunodeficiency virus (HIV) integrase (IN) catalyzes the integration of HIV DNA copy into the host cell DNA. l-Chicoric acid (1) has been found to be one of the most potent HIV-1 integrase inhibitor. Caffeoylglycolic and caffeoylamino acid derivati