N-[3’,4’-Dihydroxy-(E)-cinnamoyl]-L-glutamic Acid

Base Information

• Chemical Name: N-[3’,4’-Dihydroxy-(E)-cinnamoyl]-L-glutamic Acid
• CAS No.: 860295-23-4
• Molecular Formula: C₁₄H₁₅NO₇
• Molecular Weight: 309.276
• Mol file: 860295-23-4.mol

Synonyms:L-Glutamicacid, N-[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]- (9CI)

Chemical Property of N-[3’,4’-Dihydroxy-(E)-cinnamoyl]-L-glutamic Acid

Chemical Property:

• PSA: 144.16000
• LogP: 0.93610

Purity/Quality:

98%Min ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: It was identified in the antioxidant polyphenolic fraction of cocoa (Theobroma cacao L.). As a naturally occurring caffeoyl conjugate, it represents an interesting antiradical/antioxidant compound.

Technology Process of N-[3’,4’-Dihydroxy-(E)-cinnamoyl]-L-glutamic Acid

There total 4 articles about N-[3’,4’-Dihydroxy-(E)-cinnamoyl]-L-glutamic 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:

(S)-2-[(E)-3-(3,4-Diacetoxy-phenyl)-acryloylamino]-pentanedioic acid → (-)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-L-glutamic acid (860295-23-4)

Guidance literature:

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

DOI:10.1021/jf050458q

Reference yield:

caffeic acid (331-39-5,501-16-6) → (-)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-L-glutamic acid (860295-23-4)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine; (dimethylamino)pyridine / 1 h / 0 °C

2: thionyl chloride / 76 °C

3: tetrahydrofuran / 20 °C

4: aq. K₂CO₃ / methanol / 0.33 h / 20 °C

With pyridine; dmap; thionyl chloride; potassium carbonate; In tetrahydrofuran; methanol;

DOI:10.1021/jf050458q

Reference yield:

3,4-diacetoxycinnamic acid (88623-81-8) → (-)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-L-glutamic acid (860295-23-4)

Guidance literature:

Multi-step reaction with 3 steps

1: thionyl chloride / 76 °C

2: tetrahydrofuran / 20 °C

3: aq. K₂CO₃ / methanol / 0.33 h / 20 °C

With thionyl chloride; potassium carbonate; In tetrahydrofuran; methanol;

DOI:10.1021/jf050458q

upstream raw materials:

caffeic acid

3,4-diacetoxycinnamic acid

(E)-3,4-di-O-acetylcaffeoyl chloride

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