Isoferulic Acid

• CAS: 537-73-5
• Catalog Number: ACM537735
• Category: Inhibitors
• Molecular Weight: 194.18
• Molecular Formula: C10H10O4
• Description: Isoferulic acid (3-Hydroxy-4-methoxycinnamic acid) is a cinnamic acid derivative that has antidiabetic activity. Isoferulic acid binds to and activates α1-adrenergic receptors (IC50=1.4 µM) to enhance secretion of β-endorphin (EC50=52.2 nM) and increase glucose use. Isoferulic acid also has anti-influenza virus activities.
• Synonyms: 3-Hydroxy-4-methoxycinnamic acid
• IUPAC Name: (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid
• Canonical SMILES: COC1=C(C=C(C=C1)/C=C/C(=O)O)O
• InChI: InChI=1S/C10H10O4/c1-14-9-4-2-7(6-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+
• InChI Key: QURCVMIEKCOAJU-HWKANZROSA-N
• Boiling Point: 250.62 °C
• Melting Point: 230 °C (dec.)(lit.)
• Density: 1.058 g/ml
• Solubility: Soluble in ethanol and methanol
• Appearance: Powder
• Exact Mass: 194.0579088
• Isomeric SMILES: COC1=C(C=C(C=C1)/C=C/C(=O)O)O
• Monoisotopic Mass: 194.0579088
• Physical State: Solid
• pKa: 4.53±0.10
• Refractive Index: n20/D 1.5168(lit.)
• Storage Conditions: Dark and dry place,Room Temperature
• Topological Polar Surface Area: 66.8 Ų

Synthetic Use

Upstream Synthesis Route 1

• 621-59-0
• 141-82-2

• 537-73-5

Reference: [1] Synthetic Communications, 1995, vol. 25, # 20, p. 3187 - 3197

Upstream Synthesis Route 2

• 97966-29-5

• 537-73-5

Reference: [1] Chemistry Letters, 2005, vol. 34, # 2, p. 264 - 265

Upstream Synthesis Route 3

• 621-59-0
• 773109-21-0

• 537-73-5

Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 20, p. 2537 - 2539

Downstream Synthesis Route 1

• 186581-53-3
• 537-73-5

• 5396-64-5

Reference: [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 7785 - 7788
Angew. Chem.,2014,vol. 53,p. 7919 - 7922,4

* For details of the synthesis route, please refer to the original source to ensure accuracy.