3-(3,4-Dihydroxy-phenyl)-2-[3-(3,4-dihydroxy-phenyl)-acryloylamino]-propionic acid

Base Information

• Chemical Name: 3-(3,4-Dihydroxy-phenyl)-2-[3-(3,4-dihydroxy-phenyl)-acryloylamino]-propionic acid
• CAS No.: 53755-02-5
• Molecular Formula: C18H17NO7
• Molecular Weight: 359.335
• DSSTox Substance ID: DTXSID101046814
• Nikkaji Number: J2.025.021F
• ChEMBL ID: CHEMBL115421
• Mol file: 53755-02-5.mol

Synonyms:CHEMBL115421;(S,E)-clovamide;DTXSID101046814;BDBM50133493;N-(3,4-Dihydroxy-trans-cinnamoyl)-3,4-dihydroxy-D-phenylalanine;3-(3,4-dihydroxy-phenyl)-2-[3-(3,4-dihydroxy-phenyl)-acryloylamino]-propionic acid;(R)-3-(3,4-Dihydroxy-phenyl)-2-[(E)-3-(3,4-dihydroxy-phenyl)-acryloylamino]-propionic acid

Chemical Property of 3-(3,4-Dihydroxy-phenyl)-2-[3-(3,4-dihydroxy-phenyl)-acryloylamino]-propionic acid

Chemical Property:

• Vapor Pressure: 2.06E-25mmHg at 25°C
• Melting Point: 108-112°C
• Refractive Index: 1.722
• Boiling Point: 777°C at 760 mmHg
• Flash Point: 423.7°C
• PSA: 147.32000
• Density: 1.527g/cm³
• LogP: 1.72520
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 359.10050188
• Heavy Atom Count: 26
• Complexity: 524

Purity/Quality:

97% ^*data from raw suppliers

N-[3’,4’-Dihydroxy-(E)-cinnamoyl]-3-hydroxy-L-tyrosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1CC(C(=O)O)NC(=O)C=CC2=CC(=C(C=C2)O)O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1C[C@H](C(=O)O)NC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)O
• Uses: It was identified in the antioxidant polyphenolic fraction of cocoa (Theobroma cacao L.). pound. 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.

Technology Process of 3-(3,4-Dihydroxy-phenyl)-2-[3-(3,4-dihydroxy-phenyl)-acryloylamino]-propionic acid

There total 11 articles about 3-(3,4-Dihydroxy-phenyl)-2-[3-(3,4-dihydroxy-phenyl)-acryloylamino]-propionic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.55%

(S)-3-(3,4-dihydroxyphenyl)-2-[3-(3,4-dihydroxyphenyl)acryloylamino]propionic acid methyl ester (120094-83-9) → 3-(3,4-dihydroxy-phenyl)-2-[3-(3,4-dihydroxy-phenyl)-acryloylamino]propionic acid (53755-02-5)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 2h;

Reference yield: 54.0%

3-(3,4-dihydroxy-phenyl)-(S)-2-[3-trans-(3,4-dihydroxy-phenyl)-acryloylamino]-propionic acid methyl ester → caffeoyl DOPA (53755-02-5,53755-03-6)

Guidance literature:

With hydrogenchloride; In water; acetone;

Reference yield:

(S)-2-[(E)-3-(3,4-Diacetoxy-phenyl)-acryloylamino]-3-(3,4-dihydroxy-phenyl)-propionic acid → 3-(3,4-dihydroxy-phenyl)-2-[3-(3,4-dihydroxy-phenyl)-acryloylamino]propionic acid (53755-02-5)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 0.333333h;

DOI:10.1021/jf050458q

upstream raw materials:

levodopa

(E)-3-(3,4-dihydroxyphenyl)acryloyl chloride

caffeic acid

L-dopa methyl ester hydrochloride

Downstream raw materials:

pentamethyl-trans-clovamide