Methyl caffeate

Base Information

• Chemical Name: Methyl caffeate
• CAS No.: 3843-74-1
• Molecular Formula: C₁₀H₁₀O₄
• Molecular Weight: 194.187
• Hs Code.: 2918290000
• European Community (EC) Number: 808-143-8
• UNII: N79173B9HF
• DSSTox Substance ID: DTXSID401030290
• Nikkaji Number: J46.681F,J1.450.856B
• Wikipedia: Methyl_caffeate
• Wikidata: Q6823935
• Metabolomics Workbench ID: 53289
• ChEMBL ID: CHEMBL17001
• Mol file: 3843-74-1.mol

Synonyms:Cinnamicacid, 3,4-dihydroxy-, methyl ester (6CI,7CI,8CI);Caffeic acid methyl ester;Methyl 3,4-dihydroxycinnamate;

Chemical Property of Methyl caffeate

Chemical Property:

• Appearance/Colour: Slightly yellowish solid
• Vapor Pressure: 6.38E-06mmHg at 25°C
• Melting Point: 158-161°C
• Refractive Index: 1.628
• Boiling Point: 367.6 °C at 760 mmHg
• PKA: 8.71±0.18(Predicted)
• Flash Point: 148.3 °C
• PSA: 66.76000
• Density: 1.318 g/cm³
• LogP: 1.28400
• Storage Temp.: 0-6°C
• Solubility.: Acetonitrile (Slightly), Dimethylformamide, DMSO, Ethyl Acetate, Methanol (Sligh
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 194.05790880
• Heavy Atom Count: 14
• Complexity: 224

Purity/Quality:

99% ^*data from raw suppliers

MethylCaffeoate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C=CC1=CC(=C(C=C1)O)O
• Isomeric SMILES: COC(=O)/C=C/C1=CC(=C(C=C1)O)O
• Description: Caffeic acid methyl ester is an ester of a naturally occurring phenolic compound found in P. amplexicaule var. sinense and S. torvum fruits. At 40 mg/kg, it demonstrates antihyperglycemic and antidiabetic activity in diabetic rats, upregulating GLUT4 and regenerating pancreatic β-cells. At 10 mg/kg, it can induce anti-inflammatory and antinociceptive effects in rat models of edema and pain, inhibiting nitric oxide and prostaglandin E2 production, as well as tumor necrosis factor-α release.
• Uses: Inhibitor of protein tyrosine kinase

Technology Process of Methyl caffeate

There total 81 articles about Methyl caffeate 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:

methanol (67-56-1) + 1-O-trans-caffeoyl-5-O-trans-p-coumaroylquinic acid (1401532-34-0) → methyl 4-hydroxycinnamate (3943-97-3) + D-(-)-quinic acid (77-95-2) + Methyl caffeate (3843-74-1,67667-67-8)

Guidance literature:

With potassium hydroxide; at 20 ℃; for 2h;

DOI:10.1016/j.bmcl.2013.01.115

Reference yield:

methanol (67-56-1) + 1-O-7,8-dihydro-7α-methoxycaffeoyl-5-O-trans-caffeoylquinic acid → D-(-)-quinic acid (77-95-2) + Methyl caffeate (3843-74-1,67667-67-8) + 7,8-dihydro-7α-methoxycaffeic acid methyl ester

Guidance literature:

With potassium hydroxide; at 20 ℃; for 2h;

DOI:10.1016/j.bmcl.2013.01.115

Reference yield:

methanol (67-56-1) + 1-O-trans-caffeoyl-5-O-7,8-dihydro-7α-methoxycaffeoylquinic acid (1426417-41-5) → D-(-)-quinic acid (77-95-2) + Methyl caffeate (3843-74-1,67667-67-8) + 7,8-dihydro-7α-methoxycaffeic acid methyl ester

Guidance literature:

With potassium hydroxide; at 20 ℃; for 2h;

DOI:10.1016/j.bmcl.2013.01.115

upstream raw materials:

methanol

caffeic acid

methyl p-hydroxycinnamate

hydrogenchloride

Downstream raw materials:

methyl 3-ethoxy-4-hydroxycinnamate

methyl (2E)-3-(1,3-benzodioxol-5-yl)acrylate

4-(2-Methoxycarbonyl-vinyl)-benzochinon-(1,2)

(E)-methyl 3-(3,4-bis(methoxymethoxy)phenyl)acrylate

Refernces

• 1、 Van Dyck, Stefaan M. O.,Lemiere, Guy L. F.,Jonckers, Tim H. M.,Dommisse, Roger. "Synthesis of 4-O-Methylcedrusin. Selective protection of catechols with diphenyl carbonate". . p. 153 - 161. Retrieved 2000.
• 2、 Schwarz, Michael,Wabnitz, Tobias C.,Winterhalter, Peter. "Pathway leading to the formation of anthocyanin-vinylphenol adducts and related pigments in red wines". . p. 3682 - 3687. Retrieved 2003.
• 3、 Wang, Jun,Wang, Shasha,Li, Zhongjian,Gu, Shuangshuang,Wu, Xiangyang,Wu, Fuan. "Ultrasound irradiation accelerates the lipase-catalyzed synthesis of methyl caffeate in an ionic liquid". . p. 21 - 28. Retrieved 2015.
• 4、 Fuchino, Hiroyuki,Tachibana, Hironori,Tanaka, Nobutoshi. "Three new hemiterpene glycosides from Ilex macropoda". . p. 1533 - 1535. Retrieved 1997.
• 5、 Wang, Jun,Gu, Shuangshuang,Pang, Na,Wang, Fangqin,Wu, Fuan. "A study of the esterification of caffeic acid with methanol using p-toluenesulfonic acid as a catalyst". . p. 1023 - 1034. Retrieved 2013.
• 6、 Bernard, T.,Joucla, M.,Goas, G.,Hamelin, J.. "CARACTERISATION DE LA STICTICINE CHEZ LE LICHEN LOBARIA LAETEVIRENS". . p. 1967 - 1970. Retrieved 1980.
• 7、 Lavaud, Catherine,Massiot, Georges,Nguyen, Phuc-Dam,Sayagh, Charlotte. "Phenyl glycosides from the leaves of Flacourtia indica (Burm. f.) Merr (Salicaceae)". . . Retrieved 2021/08/06.
• 8、 -. "METHOD FOR PRODUCING CINNAMIC ACID ESTER COMPOUND". Paragraph 0066-0067; 0071; 0075. . Retrieved 2020/05/06.