3-(3-Hydroxy-4-methoxy-phenyl)-acrylic acid

Base Information

• Chemical Name: 3-(3-Hydroxy-4-methoxy-phenyl)-acrylic acid
• CAS No.: 537-73-5
• Molecular Formula: C10H10O4
• Molecular Weight: 194.187
• Hs Code.: 29189090
• DSSTox Substance ID: DTXSID80862148
• Wikidata: Q105228379
• Mol file: 537-73-5.mol

Synonyms:Spectrum_001059;SpecPlus_000233;Spectrum3_000887;Spectrum4_000979;KBioGR_001357;KBioSS_001539;DivK1c_006329;3-hydroxy4-methoxycinnamic acid;KBio1_001273;KBio2_001539;KBio2_004107;KBio2_006675;KBio3_001774;DTXSID80862148;CHEBI:189424;HMS3604H11;3-Hydroxy 4-Methoxy Cinnamic acid;AKOS024147317;LS-123654;FT-0627414;FT-0669740;3-(3-Hydroxy-4-methoxy-phenyl)-acrylic acid;D78092

Chemical Property of 3-(3-Hydroxy-4-methoxy-phenyl)-acrylic acid

Chemical Property:

• Appearance/Colour: Off-white crystalline solid
• Vapor Pressure: 1.83E-07mmHg at 25°C
• Melting Point: 230 °C (dec.)(lit.)
• Refractive Index: 1.5168 (estimate)
• Boiling Point: 410.2 °C at 760 mmHg
• PKA: 4.53±0.10(Predicted)
• Flash Point: 167.6 °C
• PSA: 66.76000
• Density: 1.316 g/cm³
• LogP: 1.49860
• Storage Temp.: -20?C Freezer
• Solubility.: Soluble in ethanol and methanol.
• 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:

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

Isoferulic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C=CC(=O)O)O
• Uses: 3-Hydroxy-4-methoxycinnamic Acid (Isoferulic acid) is a hypoglycemic agent. 3-Hydroxy-4-methoxycinnamic acid exhibits hypoglycemic properties. 3-Hydroxy-4-methoxycinnamic acid was used in the synthesis of tranilast and various tranilast analogs (cinnamoyl anthranilates) by genetically engineered Saccharomyces cerevisiae yeast strain. It was also used in the synthesis of glycoside compounds by undergoing glycosidation.

Technology Process of 3-(3-Hydroxy-4-methoxy-phenyl)-acrylic acid

There total 50 articles about 3-(3-Hydroxy-4-methoxy-phenyl)-acrylic 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: 94.0%

isovanillin (621-59-0) + malonic acid (141-82-2) → trans-3-hydroxy-4-methoxycinnamic acid (537-73-5)

Guidance literature:

With piperidine; pyridine; for 3h; Heating;

DOI:10.1080/00397919508015470

Reference yield: 81.0%

3-iodo-4-methoxy-trans-cinnamic acid (103261-25-2) → trans-3-hydroxy-4-methoxycinnamic acid (537-73-5)

Guidance literature:

With copper(I) oxide; 1-D-O-Methyl-chiro-inositol; sodium hydroxide; In water; at 120 ℃; for 6h;

DOI:10.1016/j.tetlet.2020.152222

Reference yield:

C25H30NO11S2(1-) → trans-3-hydroxy-4-methoxycinnamic acid (537-73-5)

Guidance literature:

With porcine liver esterase; In methanol; at 20 ℃; aq. phosphate buffer;

DOI:10.1016/j.phytochem.2011.01.034

upstream raw materials:

isovanillin

malonic acid

3-amino-4-methoxy-cinnamic acid

methyl (E)-3-(3-hydroxy-4-methoxyphenyl)-2-propenoate

Downstream raw materials:

methyl 3,4-dimethoxycinnamate

(E)-3-(3-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)acrylic acid

octadecyl isoferulate

1-(chloromethyl)-3-[(2E)-3-(3-hydroxy-4-methoxyphenyl)-2-propenoyl]-2,3-dihydro-1H-pyrrolo[3,2-f]quinolin-5-ol

Refernces

• 1、 Agerbirk, Niels,Olsen, Carl Erik. "Isoferuloyl derivatives of five seed glucosinolates in the crucifer genus Barbarea". . p. 610 - 623. Retrieved 2011.
• 2、 Fomum, Z. Tanee,Ayafor, J. Foyere,Wandji, Jean,Fomban, W. Gana,Nkengfack, A. Ephrem. "ERYTHRINASINATE, AN ESTER FROM THREE ERYTHRINA SPECIES". . p. 757 - 759. Retrieved 1986.
• 3、 Cui, Man-Ying,Xiao, Meng-Wu,Xu, Lv-Jie,Chen, Yun,Liu, Ai-Lin,Ye, Jiao,Hu, Ai-Xi. "Bioassay of ferulic acid derivatives as influenza neuraminidase inhibitors". . . Retrieved 2019/11/13.
• 4、 Cheng, Xi-Chuang,Guo, Xin-Ran,Liu, Hua-Min,Liu, Yu-Lan,Qin, Zhao,Wang, Xue-De. "Structural features and antioxidant activities of Chinese quince (Chaenomeles sinensis) fruits lignin during auto-catalyzed ethanol organosolv pretreatment". . p. 4348 - 4358. Retrieved 2020/09/22.