Caffeic Acid

Base Information

• Chemical Name: Caffeic Acid
• CAS No.: 501-16-6
• Molecular Formula: C₉H₈O₄
• Molecular Weight: 180.16
• Hs Code.: 2918290000
• European Community (EC) Number: 689-473-8
• NSC Number: 623438,57197
• UNII: U2S3A33KVM
• DSSTox Substance ID: DTXSID901316055
• Nikkaji Number: J1.524E,J309.143K
• Wikipedia: Caffeic_acid
• Wikidata: Q414116
• NCI Thesaurus Code: C68540
• RXCUI: 1311397
• Pharos Ligand ID: UKJGJWMDSGKD
• Metabolomics Workbench ID: 38347
• ChEMBL ID: CHEMBL145
• Mol file: 501-16-6.mol

Synonyms:3,4-dihydroxycinnamic acid;caffeic acid;caffeic acid, (E)-isomer;caffeic acid, (Z)-isomer;caffeic acid, monosodium salt;cis-caffeic acid;sodium caffeate;trans-caffeic acid

Chemical Property of Caffeic Acid

Chemical Property:

• Appearance/Colour: Yellow to tan powder
• Melting Point: 211-213 °C(lit.)
• Boiling Point: 416.8 °C at 760 mmHg
• PKA: 4.58±0.10(Predicted)
• Flash Point: 220 °C
• PSA: 77.76000
• Density: 1.478 g/cm³
• LogP: 1.19560
• Solubility.: ethanol: 50 mg/mL
• Water Solubility.: ethanol: 50 mg/mL
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 180.04225873
• Heavy Atom Count: 13
• Complexity: 212

Purity/Quality:

99% ^*data from raw suppliers

trans-Caffeic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-40-63-68-36
• Safety Statements: 26-36/37/39-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C1=CC(=C(C=C1C=CC(=O)O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1/C=C/C(=O)O)O)O
• Recent ClinicalTrials: GASC1 Inhibitor Caffeic Acid for Squamous Esophageal Cell Cancer (ESCC)
• Uses: trans-Caffeic Acid is a useful synthetic intermediate. It was used as a reactant to synthesize N-caffeoylphenalkylamide derivatives as bacterial efflux pump inhibitors. It is also used to prepare caffeic acid phenethyl ester analogs with antitumor structures.

Technology Process of Caffeic Acid

There total 170 articles about Caffeic 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:

cyanidin 3-O-[6-O-(2-O-(trans-caffeoyl)-α-arabinofuranosyl)-β-glucopyranoside]-7,3'-O-di[6-O-(trans-caffeoyl)-β-glucopyranoside] → cyanidin (13306-05-3) + L-arabinose (5328-37-0) + D-glucose (50-99-7) + caffeic acid (331-39-5,501-16-6)

Guidance literature:

Acidic conditions;

DOI:10.3987/COM-10-12012

Reference yield:

chlorogenic acid (1049703-62-9) → caffeic acid (331-39-5,501-16-6) + 1,3,4,5-tetrahydroxy-cyclohexanecarboxylic acid (77-95-2,1010-25-9,7216-27-5,23804-29-7,23804-41-3,23804-44-6,36413-60-2,135558-83-7,135558-85-9,470-63-3,562-73-2,23804-34-4,23804-38-8) + 3,5-dicaffeoylquinic acid (2450-53-5,16758-05-7,89919-61-9,89919-62-0,101222-97-3)

Guidance literature:

at 30 ℃; for 0.5h; pH 6.4; enzyme from Ipomoea batatas;

Reference yield:

nepetin-7-O-(6″-O-caffeoyl)-β-D-glucopyranoside → eupafolin (520-11-6) + D-glucose (50-99-7) + caffeic acid (331-39-5,501-16-6)

Guidance literature:

With trifluoroacetic acid; at 110 ℃; for 2h;

DOI:10.1007/s10600-019-02662-2

upstream raw materials:

malonic acid

3,4-dihydroxybenzaldehyde

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

(E)-3-phenylacrylic acid

Downstream raw materials:

3-aetoxy-4-hydroxycinnamic acid

methyl (E)-3-(3-hydroxy-4-methoxyphenyl)-2-propenoate

methyl 3,4-dimethoxycinnamate

5'-phenysulfonylcaffeic acid

Refernces

• 1、 Ali, Wajid,Anjana, S. S.,Bhattacharya, Trisha,Chandrashekar, Hediyala B.,Goswami, Nupur,Guin, Srimanta,Maiti, Debabrata,Panda, Sanjib,Prakash, Gaurav,Saha, Argha,Sasmal, Sheuli,Sinha, Soumya Kumar. "Photoinduced Regioselective Olefination of Arenes at Proximal and Distal Sites". supporting information. p. 1929 - 1940. Retrieved 2022/02/01.
• 2、 Yu, Liang,Zhu, Ling-Juan,Wang, An-Hua,Qin, Yu,Zhang, Xue,Jia, Jing-Ming,Yao, Xin-Sheng. "Anti-inflammatory glycosides from the roots of Paeonia intermedia C. A. Meyer". . p. 1452 - 1458. Retrieved 2019/08/30.