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% ^*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 (E)-3-(3-hydroxy-4-methoxyphenyl)-2-propenoate

dihydroisoferulic acid

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

methyl 3,4-dimethoxycinnamate

Refernces

Synthesis and antibacterial activity of difluoromethyl cinnamoyl amides

10.3390/molecules25040789

The research focuses on the synthesis and antibacterial activity of a series of novel di?uoromethyl cinnamoyl amides derived from isoferulic acid. The study aims to address the growing problem of antimicrobial resistance by developing new chemical entities with potential antibacterial properties. The researchers synthesized a range of amides by replacing the phenolic hydroxyl group with a di?uoromethyl moiety and tested their in vitro antibacterial activities against fourteen bacterial strains, including both Gram-positive and Gram-negative bacteria. The di?uoromethyl group was introduced using Deoxo?uor? as the fluorinating agent, and the synthesized compounds were characterized using 1H and 13C-NMR spectroscopy and mass spectrometry. The most promising compounds, such as N-isopropyl, N-isopentyl, and N-(2-phenylethyl) amides, exhibited significant antibacterial activity against Mycobacterium smegmatis with minimal cytotoxicity. The study highlights the potential of these compounds as leads for the development of narrow-spectrum antibiotics against M. tuberculosis.