3-(4-Hydroxy-3-methoxyphenyl)propionic acid

Base Information

• Chemical Name: 3-(4-Hydroxy-3-methoxyphenyl)propionic acid
• CAS No.: 1135-23-5
• Molecular Formula: C10H12 O4
• Molecular Weight: 196.203
• Hs Code.: 2918990090
• European Community (EC) Number: 214-489-5
• UNII: O01RNC700M
• DSSTox Substance ID: DTXSID90150427
• Nikkaji Number: J203.383F
• Wikidata: Q10395564
• Metabolomics Workbench ID: 67635
• ChEMBL ID: CHEMBL387842
• Mol file: 1135-23-5.mol

Synonyms:dihydroferulic acid

Chemical Property of 3-(4-Hydroxy-3-methoxyphenyl)propionic acid

Chemical Property:

• Vapor Pressure: 2.45E-06mmHg at 25°C
• Melting Point: 89-90oC
• Boiling Point: 376.5oC at 760 mmHg
• PKA: 4.73±0.10(Predicted)
• Flash Point: 151.1oC
• PSA: 66.76000
• Density: 1.259±0.06 g/cm3(Predicted)
• LogP: 1.41800
• Solubility.: Soluble in dimethyl sulfoxide and methanol.
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 196.07355886
• Heavy Atom Count: 14
• Complexity: 193

Purity/Quality:

98% ^*data from raw suppliers

DihydroFerulicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)CCC(=O)O)O
• Uses: A caffeine metabolite which showed high antioxidant activity. It is a very sensitive biomarker for the consumption of relatively small amount of coffee. 3-(4-Hydroxy-3-methoxyphenyl)propionic acid (hydroferulic acid) was used to inhibit prostaglandin E(2) production.

Technology Process of 3-(4-Hydroxy-3-methoxyphenyl)propionic acid

There total 23 articles about 3-(4-Hydroxy-3-methoxyphenyl)propionic 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: 100.0%

ethyl 3-(4-hydroxy-3-methoxyphenyl)propanoate (61292-90-8) → 3-(4-hydroxy-3-methoxyphenyl)propionic acid (1135-23-5)

Guidance literature:

With potassium hydroxide; water; In tetrahydrofuran; at 20 ℃;

Reference yield: 93.0%

β-(4-benzyloxy-3-methoxyphenyl)propionic acid (30034-49-2) → 3-(4-hydroxy-3-methoxyphenyl)propionic acid (1135-23-5)

Guidance literature:

With triethylammonium formate; palladium on activated charcoal; for 1h; Ambient temperature;

Reference yield: 83.0%

3-(4-(ethanoyloxy)-3-methoxyphenyl)propanoic acid (55417-34-0) → 3-(4-hydroxy-3-methoxyphenyl)propionic acid (1135-23-5)

Guidance literature:

With water; sodium hydroxide; for 5h; Reflux;

DOI:10.1039/c0gc00150c

upstream raw materials:

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

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

diethyl 2-(4-hydroxy-3-methoxybenzylidene)malonate

2-cyano-3-(4-hydroxy-3-methoxyphenyl)acrylic acid ethyl ester

Downstream raw materials:

ethyl 3-(4-hydroxy-3-methoxyphenyl)propanoate

(Z)-2-Cyano-3-hydroxy-5-(4-hydroxy-3-methoxy-phenyl)-pent-2-enoic acid tert-butyl ester

β-(4-benzyloxy-3-methoxyphenyl)propionic acid

benzyl 3-[4-(benzyloxy)-3-methoxyphenyl]propanoate

Refernces

• 1、 Moridani, Majid Y,Scobie, Hugh,O'Brien, Peter J. "Metabolism of caffeic acid by isolated rat hepatocytes and subcellular fractions". . p. 141 - 151. Retrieved 2002.
• 2、 ElSohly, Adel M.,MacDonald, James I.,Hentzen, Nina B.,Aanei, Ioana L.,El Muslemany, Kareem M.,Francis, Matthew B.. "ortho-Methoxyphenols as Convenient Oxidative Bioconjugation Reagents with Application to Site-Selective Heterobifunctional Cross-Linkers". . p. 3767 - 3773. Retrieved 2017.
• 3、 Abbate, Sara,Alfei, Silvana,Brullo, Chiara,Bruno, Olga,Massa, Matteo,Parisini, Emilio,Prosdocimi, Tommaso,Rapetti, Federica,Semrau, Marta,Storici, Paola,Torretta, Archimede. "Design, synthesis, biological evaluation and structural characterization of novel GEBR library PDE4D inhibitors". . . Retrieved 2021.
• 4、 Beck, John J.,Kim, Jong H.,Campbell, Bruce C.,Chou, Shen-Chieh. "Fungicidal activities of dihydroferulic acid alkyl ester analogues". . p. 779 - 782. Retrieved 2007.
• 5、 Mialon, Laurent,Pemba, Alexander G.,Miller, Stephen A.. "Biorenewable polyethylene terephthalate mimics derived from lignin and acetic acid". . p. 1704 - 1706. Retrieved 2010.
• 6、 Zhou, Yu,Fu, Yan,Yin, Wanchao,Li, Jian,Wang, Wei,Bai, Fang,Xu, Shengtao,Gong, Qi,Peng, Tao,Hong, Yu,Zhang, Dong,Zhang, Dan,Liu, Qiufeng,Xu, Yechun,Xu, H. Eric,Zhang, Haiyan,Jiang, Hualiang,Liu, Hong. "Kinetics-Driven Drug Design Strategy for Next-Generation Acetylcholinesterase Inhibitors to Clinical Candidate". . p. 1844 - 1855. Retrieved 2021/03/01.
• 7、 Bomon, Jeroen,Bal, Mathias,Achar, Tapas Kumar,Sergeyev, Sergey,Wu, Xian,Wambacq, Ben,Lemière, Filip,Sels, Bert F.,Maes, Bert U. W.. "Efficient demethylation of aromatic methyl ethers with HCl in water". supporting information. p. 1995 - 2009. Retrieved 2021/03/26.