2-METHOXYCINNAMIC ACID

Base Information

• Chemical Name: 2-METHOXYCINNAMIC ACID
• CAS No.: 1011-54-7
• Molecular Formula: C10H10 O3
• Molecular Weight: 178.188
• Hs Code.: 2916399090
• European Community (EC) Number: 228-047-4,213-785-1
• NSC Number: 638141,8135
• UNII: J77SK1Y4MY
• DSSTox Substance ID: DTXSID60901605
• Nikkaji Number: J135.442F,J227.295D
• Metabolomics Workbench ID: 143564
• ChEMBL ID: CHEMBL95203
• Mol file: 1011-54-7.mol

Synonyms:2-Propenoicacid, 3-(2-methoxyphenyl)-, (E)-; Cinnamic acid, o-methoxy-, (E)- (8CI);Cinnamic acid, o-methoxy-, trans- (7CI); (E)-2-Methoxycinnamic acid;(E)-3-(2-Methoxyphenyl)-2-propenoic acid; (E)-3-(2-Methoxyphenyl)acrylic acid;(E)-o-Methoxycinnamic acid; trans-2-Methoxycinnamic acid;trans-3-(2-Methoxyphenyl)-2-propenoic acid; trans-o-Methoxycinnamic acid

Chemical Property of 2-METHOXYCINNAMIC ACID

Chemical Property:

• Vapor Pressure: 9.64E-05mmHg at 25°C
• Melting Point: 182-186 °C
• Boiling Point: 325.1°Cat760mmHg
• PKA: 4.47±0.10(Predicted)
• Flash Point: 130.3°C
• PSA: 46.53000
• Density: 1.195g/cm³
• LogP: 1.79300
• Solubility.: almost transparency in hot Methanol
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 178.062994177
• Heavy Atom Count: 13
• Complexity: 198

Purity/Quality:

98%,99%, ^*data from raw suppliers

trans-2-Methoxycinnamic Acid >99.0%(T) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC=C1C=CC(=O)O
• Isomeric SMILES: COC1=CC=CC=C1/C=C/C(=O)O
• Uses: (E)-3-(2-Methoxyphenyl)acrylic Acid is a noncompetitive inhibitor of tyrosinase.

Technology Process of 2-METHOXYCINNAMIC ACID

There total 41 articles about 2-METHOXYCINNAMIC 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: 95.0%

malonic acid (141-82-2) + ortho-anisaldehyde (135-02-4) → 2-methoxycinnamic acid (1011-54-7)

Guidance literature:

With piperazine; for 0.0666667h; microwave irradiation;

Reference yield: 95.0%

(E)-3-(2-methoxyphenyl)propenal (60125-24-8) → 2-methoxycinnamic acid (1011-54-7)

Guidance literature:

With 1-hydroxy-pyrrolidine-2,5-dione; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 20 ℃; for 16h;

DOI:10.1002/1521-3773(20021104)41:21<4059::AID-ANIE4059>3.0.CO;2-R

Reference yield: 95.0%

4-iodoanisol (529-28-2) + acrylic acid (79-10-7) → 2-methoxycinnamic acid (1011-54-7)

Guidance literature:

With triethylamine; poly{bis[(N-iPr-acrylamide)5-co-((4-vinylphenyl)PPh₂)]PdCl₂}; In water; at 100 ℃; for 24h;

DOI:10.1016/j.tet.2004.02.068

upstream raw materials:

2-methoxycinnamaldehyde

(E)-2-cyano-3-(2-methoxyphenyl)-2-propenoic acid ethyl ester

3-hydroxy-3-(2-methoxy-phenyl)-propionic acid

3-methoxy-3-(2-methoxy-phenyl)-propionic acid

Downstream raw materials:

o-methoxystyrene

ethyl 3-(2-methoxyphenyl)prop-2-enoate

2-bromo-3-(5-bromo-2-methoxy-phenyl)-3-hydroxy-propionic acid

3-hydroxy-3-(2-methoxy-phenyl)-propionic acid

Refernces

• 1、 Konno, Hiroyuki,Wakabayashi, Masaki,Takanuma, Daiki,Saito, Yota,Akaji, Kenichi. "Design and synthesis of a series of serine derivatives as small molecule inhibitors of the SARS coronavirus 3CL protease". . p. 1241 - 1254. Retrieved 2016.
• 2、 Rodrigues-Santos, Cláudio E.,Echevarria, Aurea. "An efficient and fast synthesis of 4-aryl-3,4-dihydrocoumarins by (CF3SO3)3Y catalysis under microwave irradiation". . p. 4505 - 4508. Retrieved 2007.
• 3、 Zhao, Xiaodan,Alper, Howard,Yu, Zhengkun. "Stereoselective hydroxycarbonylation of vinyl bromides to α,β-unsaturated carboxylic acids in the ionic liquid [BMIM]PF 6". . p. 3988 - 3990. Retrieved 2006.
• 4、 Scheffer et al.. "-". . p. 1653. Retrieved 1967.
• 5、 Bellassoued, Moncef,Lensen, Nathalie,Bakasse, Mina,Mouelhi, Sinda. "Two-carbon homologation of aldehydes via silyl ketene acetals: A new stereoselective approach to (E)-alkenoic acids". . p. 8785 - 8789. Retrieved 1998.
• 6、 Maekawa, Yasunari,Inaba, Tomonori,Hobo, Hiroki,Narita, Tadashi,Koshikawa, Hiroshi,Moon, Seongyun,Kato, Jun,Yoshida, Masaru. "Radiation-induced reactions via the lowest excited states in cinnamic acid crystals". . p. 2088 - 2089. Retrieved 2002.
• 7、 Cheng, Jianjun,Fan, Luyu,Liu, Ruiquan,Tan, Liang,Wang, Huan,Wang, Sheng,Yan, Wenzhong,Yu, Jing. "2-Phenylcyclopropylmethylamine Derivatives as Dopamine D2Receptor Partial Agonists: Design, Synthesis, and Biological Evaluation". . p. 17239 - 17258. Retrieved 2021/12/06.
• 8、 Patra, Debabrata,Panja, Subir,Saha, Amit. "C–C Cross-Coupling Reactions of Organosilanes with Terminal Alkenes and Allylic Acetates Using PdII Catalyst Supported on Starch Coated Magnetic Nanoparticles". supporting information. p. 878 - 883. Retrieved 2020/02/13.