3,4-Dihydroxy cinnamic acid

Base Information

• Chemical Name: 3,4-Dihydroxy cinnamic acid
• CAS No.: 331-39-5
• Molecular Formula: C9H8O4
• Molecular Weight: 180.16
• Hs Code.: 2916.39 DERIVATION
• DSSTox Substance ID: DTXSID5020231
• Wikidata: Q56231106
• Metabolomics Workbench ID: 130588
• ChEMBL ID: CHEMBL3181904
• Mol file: 331-39-5.mol

Synonyms:(E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid;DTXSID5020231;MFCD00004392;Caffeic acid 1000 microg/mL in Acetone;3,4-dihydroxycinnamic acid (caffeic acid);Spectrum_001686;SpecPlus_000528;Prestwick0_000902;Prestwick1_000902;Spectrum2_001612;Spectrum4_001694;3,4-dihydroxy cinnamic acid;KBioGR_001988;KBioSS_002166;DivK1c_006624;SPBio_001643;SPBio_002943;CHEMBL3181904;KBio1_001568;KBio2_002166;KBio2_004734;KBio2_007302;HMS1570F06;HMS2097F06;HMS3371E09;HMS3655J20;AKOS025243986;3-(3,4-Dihydroxy-phenyl)-acrylic acid;NCGC00017364-14;NCI60_004400;SY009299;caffeic acid (3,4-dihydroxycinnamic acid);FT-0614329;FT-0664186;FT-0693125;Q56231106

Chemical Property of 3,4-Dihydroxy cinnamic acid

Chemical Property:

• Appearance/Colour: Light yellow to greenish-yellow powder
• Vapor Pressure: 1.08E-07mmHg at 25°C
• Melting Point: 211-213 °C (dec.)(lit.)
• Refractive Index: 1.4500 (estimate)
• 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
• Storage Temp.: Store at RT.
• Solubility.: ethanol: 50 mg/mL
• Water Solubility.: soluble in hot water
• 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

Caffeic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C=CC(=O)O)O)O
• Uses: 1. Reagents for Organic Synthesis. 2. Intermediate of caffeic acid; can be used in organic synthesis. 3. Used for Biochemical studies. Caffeic acid has been used as a standard of phenolic acid in the study to determine the total phenolic acid content in vegetables after subjecting to alkaline and acid hydrolysis. It has also been used to determine its antioxidant activity by various assay methods. antineoplastic, PGE2 synthase inhibitor, PK inhibitor Caffeic Acid is a constituent of plants, probably occurs in plants only in conjugated forms. Caffeic acid is found in all plants because it is a key intermediate in the biosynthesis of lignin, one of the principal sources of biomass. Caffeic acid is one of the main natural phenols in argan oi.
• Description: Caffeic acid is abundant in the whole plant of Solidago decurrens Lour. (Yi Zhi Huang Hua), fruit of Crataegus pinnatifida Bge. var. major N.E.Br. (Shan Li Hong), Salix myrtillacea Anderss. (Po Liu), rhizome of Cimicifuga foetida L., rhizome of Polypodiaceae Polypodium vulgare L. (Ou Ya Shui Long Gu), peel of Rutaceae Citrus limonum (Ning Meng), the whole plant of Polygonaceae Polygonum aviculare L. (Pian Xu), root of Valeriana officinalis L. (Xie Cao), the whole plant of Thymus mongolicus Ronn (She Xiang), leaves of Eucommia ulmoides (Du Zhong), and other herbal plants. It is a kind of polyhydroxy styrene acid, with the general chemical properties of phenolic acid. It is easily oxidized for the reason of the unsaturated double bonds, particularly unstable in alkaline solutionCaffeic acid has both cis and trans isomers, and the two isomers of caffeic acid have a mutual transformation in plants, which may regulate some important physiological process. Caffeic acid exists in plants in the main form of complexes; free state accounts for a few proportion. Caffeic acid is an inhibitor of 5-LO with an IC50 value of 3.7-72 μM and 12-LO with an IC50 value of 5.1-30 μM.
• Physical properties: Appearance: yellow crystal. The crystal from the concentrated solution does not contain crystal water, and the crystal from the dilute solution contains one molecule crystal water. Melting point: 223?225?°C. Solubility: It is slightly soluble in coldwater but soluble in hot water, cold ethanol, and ethyl acetate. The basic solution is orange-red. Ferric chloride solution was dark green.
• Indications: It is used for preventing or stopping bleeding during surgery, as well as hemostasis in the department of medicine, obstetrics and gynecology, etc. It is also used for various causes of neutropenia and thrombocytopenia.

Technology Process of 3,4-Dihydroxy cinnamic acid

There total 169 articles about 3,4-Dihydroxy cinnamic 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:

methyl 2,5-di-O-caffeyl-α-L-arabinofuranoside

(R)-(+)-rosmarinic acid

malonic acid

3,4-dihydroxybenzaldehyde

Downstream raw materials:

Methyl caffeate

methyl 3,4-dihydroxycinnamate

n-propyl caffeate

ethyl caffeate

Refernces

• 1、 Sakurai, Atsushi,Kato, Takahiko. "A New Glycoside, Kusaginin Isolated from Clerodendron trichotomum". . p. 1573 - 1574. Retrieved 1983.
• 2、 Pomilio,Sproviero. "". . p. 2323,2325. Retrieved 1972.
• 3、 Yang et al.. "". . p. 658,659,660. Retrieved 1960.
• 4、 Pan, Yingni,Morikawa, Toshio,Ninomiya, Kiyofumi,Imura, Katsuya,Yuan, Dan,Yoshikawa, Masayuki,Muraoka, Osamu. "Bioactive constituents from Chinese natural medicines. XXXVI.1) four new acylated phenylethanoid oligoglycosides, kankanosides J1, J2, K1, and K2, from stems of cistanche tubulosa". . p. 575 - 578. Retrieved 2010.
• 5、 Kallinich, Constanze,Schefer, Simone,Rohn, Sascha. "Analysis of protein-phenolic compound modifications using electrochemistry coupled to mass spectrometry". . . Retrieved 2018.
• 6、 Luecha, Prathan,Umehara, Kaoru,Miyase, Toshio,Noguchi, Hiroshi. "Antiestrogenic constituents of the Thai medicinal plants Capparis flavicans and Vitex glabrata". . p. 1954 - 1959. Retrieved 2009.
• 7、 Hussein, Sahar A.M.,Ayoub, Nahla A.,Nawwar, Mahmoud A.M.. "Caffeoyl sugar esters and an ellagitannin from Rubus sanctus". . p. 905 - 911. Retrieved 2003.
• 8、 De Rosa, Salvatore,Mitova, Maya,Handjieva, Nedjalka,Cals, Ihsan. "Coumarin glucosides from Cruciata taurica". . p. 447 - 450. Retrieved 2002.
• 9、 Wang, Kui-Wu,Sun, Cui-Rong,Wu, Xiao-Dan,Pan, Yuan-Jiang. "Novel bioactive dammarane caffeoyl esters from Celastrus rosthornianus". . p. 370 - 372. Retrieved 2006.
• 10、 Jiang, Zhi-Hong,Wang, Jing-Rong,Li, Min,Liu, Zhong-Qiu,Chau, Ka-Yee,Zhao, Chi,Liu, Liang. "Hemiterpene glucosides with anti-platelet aggregation activities from Ilex pubescens". . p. 397 - 399. Retrieved 2005.