53755-02-5

Usage

Uses

Used in Antioxidant Applications:
N-[3’,4’-Dihydroxy-(E)-cinnamoyl]-3-hydroxy-L-tyrosine is used as an antioxidant compound for its ability to neutralize free radicals and protect cells from oxidative damage. Its presence in the antioxidant polyphenolic fraction of cocoa highlights its potential as a natural additive in the food and pharmaceutical industries to enhance the shelf life and health benefits of products.
Used in Pharmaceutical Industry:
N-[3’,4’-Dihydroxy-(E)-cinnamoyl]-3-hydroxy-L-tyrosine is used as a pharmaceutical candidate for its potential therapeutic applications. Its antioxidant properties make it a promising agent for the development of drugs targeting various diseases associated with oxidative stress, such as neurodegenerative disorders, cardiovascular diseases, and certain types of cancer.
Used in Cosmetics Industry:
In the cosmetics industry, N-[3’,4’-Dihydroxy-(E)-cinnamoyl]-3-hydroxy-L-tyrosine is used as an active ingredient for its antioxidant and anti-aging properties. It can be incorporated into skincare products to protect the skin from environmental stressors, reduce the visible signs of aging, and promote a healthier, more youthful appearance.
Used in Food Industry:
N-[3’,4’-Dihydroxy-(E)-cinnamoyl]-3-hydroxy-L-tyrosine is used as a natural antioxidant additive in the food industry to extend the shelf life of products and enhance their nutritional value. Its presence in cocoa beans suggests potential applications in the chocolate and cocoa products sector, where it can contribute to improved taste, texture, and health benefits.

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

Downstream Products

• 64803-83-4 pentamethyl-trans-clovamide 

Relevant academic research and scientific papers

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.

Rosmarinic acid derivative as well as preparation method and application thereof

The invention relates to a rosmarinic acid derivative as well as a preparation method thereof. The rosmarinic acid analog provided by the invention or a salt which comprises a medicine of the analog and is clinically acceptable has good application prospe

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.

The structure-activity relationship of the series of non-peptide small antagonists for p56lck SH2 domain

The antagonists for the SH2 domain are regarded as novel therapeutic candidates for cancer, autoimmune disease, and chronic inflammatory disease. Previously, we identified rosmarinic acid (α-o-caffeoyl-3,4-dihydroxyphenyl-lactic acid; RosA) from Prunella vulgaris as an antagonist for the p56lck SH2 domain by screening natural products. RosA not containing phosphotyrosine surrogate had a considerable inhibitory activity for T-cell antigen receptor (TCR)-induced interleukin (IL)-2 expression, and subsequent T-cell proliferation in vitro cell assay. To investigate the structure-activity relationship of RosA and to identify a novel p56lck SH2 antagonist with more potent in vitro T-cell inhibitory activity, we synthesized several analogs of RosA by using rational design. All synthesized compounds were tested in vitro binding activity for the SH2 domain and in vitro T-cell inhibitory activity. All four hydroxyl groups of RosA were essential for binding with the p56lck SH2 domain and T-cell inhibitory activity. Unexpectedly, conformationally less constrained analogs 4 and 9 showed a more potent binding affinity for the SH2 domain than that of RosA, and chirality of the analog did not play an important role in protein binding. We successfully identified several RosA analogs with a more potent T-cell inhibitory activity than that of RosA. Overall results revealed important structural requirements of the p56lck SH2 antagonists for in vitro T-cell inhibitory activity and in vitro protein binding activity.

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

Isolation, structure determination, synthesis, and sensory activity of N-phenylpropenoyl-L-amino acids from cocoa (Theobroma cacao)

Application of chromatographic separation and taste dilution analyses recently revealed besides procyanidins a series of N-phenylpropenoyl amino acids as the key contributors to the astringent taste of nonfermented cocoa beans as well as roasted cocoa nib

Derivatives of hydroxyphenyl, a method for preparing thereof and their pharmaceutical composition

The present invention relates to derivatives of hydroxyphenyl, a method for preparing thereof and their pharmaceutical composition, more particularly the compounds of the present invention specifically inhibit the activation of T lymphocyte by src homology region 2(SH2) domain of T lymphocyte (lck), so that they can be used for the treatment, prevention and/or diagnosis of graft rejection, autoimmune diseases, inflammatory diseases, etc.

Derivatives of hydroxyphenyl, a method for preparing thereof and their pharmaceutical composition

The present invention relates to derivatives of hydroxyphenyl, a method for preparing thereof and their pharmaceutical composition, more particularly the compounds of the present invention specifically inhibit the activation of T lymphocyte by src homology region 2(SH2) domain of T lymphocyte (lck), so that they can be used for the treatment, prevention and/or diagnosis of graft rejection, autoimmune diseases, inflammatory diseases, etc.

Isolation and synthesis of trans- and cis-(-)-clovamides and their deoxy analogues from the bark of Dalbergia melanoxylon

N-(3′,4′-Dihydroxy-trans-cinnamoyl)-3-(3,4-dihydroxyphenyl)-L-alanine [(-)-clovamide], the major phenolic metabolite (0.1%) in the bark of Dalbergia melanoxylon, is associated with minor proportions of its cis-isomer, and similar pairs of geometrical isomers of their deoxy analogues N-(4′-hydroxycinnamoyl)-3-(3,4-dihydroxyphenyl)-L-alanine and N-(4′-hydroxycinnamoyl)-3-(4-hydroxyphenyl)-L-alanine. (-)-Trans-clovamide is synthesized by direct condensation of the acid chloride of caffeic acid with L-DOPA. Diagnostic CD spectra of these compounds and 13C spectra of (-)-trans- and (-)-cis-clovamides are recorded.