3,4,5-Trihydroxycinnamic acid

Base Information

• Chemical Name: 3,4,5-Trihydroxycinnamic acid
• CAS No.: 6093-59-0
• Molecular Formula: C9H8O5
• Molecular Weight: 196.16
• European Community (EC) Number: 836-123-9
• NSC Number: 153688
• Nikkaji Number: J585.641H,J881.715D
• ChEMBL ID: CHEMBL228045
• Mol file: 6093-59-0.mol

Synonyms:3,4,5-trihydroxycinnamic acid

Chemical Property of 3,4,5-Trihydroxycinnamic acid

Chemical Property:

• Vapor Pressure: 7.07E-11mmHg at 25°C
• Melting Point: 207-208 °C (decomp)
• Boiling Point: 501.5°Cat760mmHg
• PKA: 4.53±0.10(Predicted)
• Flash Point: 271.2°C
• PSA: 97.99000
• Density: 1.63g/cm³
• LogP: 0.90120
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 196.03717335
• Heavy Atom Count: 14
• Complexity: 225

Purity/Quality:

99%min ^*data from raw suppliers

3,4,5-TrihydroxycinnamicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1O)O)O)C=CC(=O)O
• Isomeric SMILES: C1=C(C=C(C(=C1O)O)O)/C=C/C(=O)O
• Uses: 3,4,5-Trihydroxycinnamic Acid can be used for its anti-asthmatic effects in vitro and in vivo.

Technology Process of 3,4,5-Trihydroxycinnamic acid

There total 15 articles about 3,4,5-Trihydroxycinnamic 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: 86.0%

malonic acid (141-82-2) + gallaldehyde (13677-79-7) → trans-3-(3,4,5-trihydroxyphenyl)-2-propenoic acid (6093-59-0,709007-50-1)

Guidance literature:

With piperidine; pyridine; at 65 ℃;

DOI:10.1002/cmdc.201800352

Reference yield: 86.0%

caffeic acid (331-39-5,501-16-6) → trans-3-(3,4,5-trihydroxyphenyl)-2-propenoic acid (6093-59-0,709007-50-1)

Guidance literature:

With sodium dihydrogenphosphate; at 25 ℃; for 0.25h; pH=7; Reagent/catalyst; Time; Glovebox;

DOI:10.1021/acscatal.5b00439

Reference yield: 70.0%

malonic acid (141-82-2) + gallaldehyde (13677-79-7) → 3,4,5‐trihydroxycinnamic acid (6093-59-0,709007-50-1)

Guidance literature:

malonic acid; gallaldehyde; With pyridine; at 55 ℃;

With piperidine; aniline; at 20 ℃; for 1h;

DOI:10.1016/S0045-2068(03)00042-7

upstream raw materials:

piperidine

ethanol

malonic acid

gallaldehyde

Downstream raw materials:

methyl 3,4,5-trimethoxycinnamate

(Z)-3,4,5-trihydroxycinnamic acid

3-(4,5-dihydroxy-3-methoxyphenyl)prop-2-enoic acid

Refernces

• 1、 Esteves, Mario,Siquet, Christophe,Gaspar, Alexandra,Rio, Vitor,Sousa, Joana B.,Reis, Salette,Marques, Maria P. M.,Borges, Fernanda. "Antioxidant versus cytotoxic properties of hydroxycinnamic acid derivatives - A new paradigm in phenolic research". . p. 164 - 173. Retrieved 2008.
• 2、 Misawa, Naoki,Hosoya, Takahiro,Yoshida, Shuhei,Sugimoto, Osamu,Yamada-Kato, Tomoe,Kumazawa, Shigenori. "5-Hydroxyferulic acid methyl ester isolated from wasabi leaves inhibits 3T3-L1 adipocyte differentiation". . p. 1304 - 1310. Retrieved 2018/03/01.
• 3、 Dhammaraj, Taweesak,Phintha, Aisaraphon,Pinthong, Chatchadaporn,Medhanavyn, Dheeradhach,Tinikul, Ruchanok,Chenprakhon, Pirom,Sucharitakul, Jeerus,Vardhanabhuti, Nontima,Jiarpinitnun, Chutima,Chaiyen, Pimchai. "p-Hydroxyphenylacetate 3-Hydroxylase as a Biocatalyst for the Synthesis of Trihydroxyphenolic Acids". . p. 4492 - 4502. Retrieved 2015/08/18.