Isoferulic acid

Base Information

• Chemical Name: Isoferulic acid
• CAS No.: 25522-33-2
• Molecular Formula: C₁₀H₁₀O₄
• Molecular Weight: 194.187
• Hs Code.: 29189090
• European Community (EC) Number: 208-676-0
• NSC Number: 51987
• UNII: XSQ2K2G7MC
• DSSTox Substance ID: DTXSID901314847
• Nikkaji Number: J6.365G,J250.490A
• Wikipedia: Isoferulic_acid
• Wikidata: Q27096447
• Pharos Ligand ID: XQW5UWKHQDSF
• Metabolomics Workbench ID: 37518
• ChEMBL ID: CHEMBL233295
• Mol file: 25522-33-2.mol

Synonyms:3-hydroxy-4-methoxycinnamic acid;isoferulic acid

Chemical Property of Isoferulic acid

Chemical Property:

• Melting Point: 230?°C (dec.)(lit.)
• Refractive Index: 1.5168 (estimate)
• Boiling Point: 410.2°Cat760mmHg
• PKA: 4.53±0.10(Predicted)
• Flash Point: 167.6°C
• PSA: 66.76000
• Density: 1.316g/cm³
• LogP: 1.49860
• Storage Temp.: 2-8°C
• 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%min ^*data from raw suppliers

Safty Information:

• Pictogram(s): 2212760
• Hazard Codes: 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
• Isomeric SMILES: COC1=C(C=C(C=C1)/C=C/C(=O)O)O
• Uses: 3-Hydroxy-4-methoxycinnamic acid, trans-Isoferulic acid

Technology Process of Isoferulic acid

There total 27 articles about Isoferulic 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: 98.0%

isovanillin (621-59-0) + malonic acid (141-82-2) → isoferulic acid (537-73-5,1135-16-6,25522-33-2)

Guidance literature:

With piperidine; In pyridine; at 105 ℃; for 3h; Reflux; Inert atmosphere;

DOI:10.1002/chem.201502450

Reference yield: 81.0%

3-(3-iodo-4-methoxybenzene)acrylic acid (103261-25-2) → isoferulic acid (537-73-5,1135-16-6,25522-33-2)

Guidance literature:

With copper(I) oxide; 1D-1-O-Methyl-muco-inostol; sodium hydroxide; In water; at 100 ℃; for 6h;

Reference yield:

dewaxed lignin from Chinese quince fruits (Chaenomeles sinensis), extracted at 140 °C over 90 min by 60% ethanol-water mixture → 4-ethyl-1,3-benzenediol (2896-60-8) + p-cresol (106-44-5) + 1,3-dimethoxy-2-hydroxy-benzene (91-10-1) + 2-Methoxy-4-methylphenol (93-51-6) + 1,2,3-trimethoxybenzene (634-36-6) + 2,4,6-trihydroxyacetophenone (480-66-0,67471-34-5) + 4-allyl-2,6-dimethoxyphenol (6627-88-9) + 1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone (2478-38-8) + 3-methoxy-4-hydroxystyrene (7786-61-0,31853-85-7) + 4-Ethylguaiacol (2785-89-9) + 1-(4-hydroxy-3-methoxyphenyl)2-propanone (2503-46-0) + isoferulic acid (537-73-5,1135-16-6,25522-33-2) + benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) + ortho-cresol (95-48-7,77504-84-8) + 2-methoxy-phenol (90-05-1) + 4-methyl-1,2-dihydroxybenzene (452-86-8) + phenol (108-95-2,27073-41-2)

Guidance literature:

at 500 ℃; for 0.00555556h; Pyrolysis;

DOI:10.1016/j.ijbiomac.2020.08.249

upstream raw materials:

isovanillin

malonic acid

3-amino-4-methoxy-cinnamic acid

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

Downstream raw materials:

dihydroisoferulic acid

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

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

Refernces

• 1、 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.
• 2、 Tang, Qingyun,Bornscheuer, Uwe T.,Pavlidis, Ioannis V.. "Specific Residues Expand the Substrate Scope and Enhance the Regioselectivity of a Plant O-Methyltransferase". . p. 3227 - 3233. Retrieved 2019/07/04.