methyl 3-(4-hydroxyphenyl)prop-2-enoate

• ChemBase ID: 44213
• Molecular Formular: C10H10O3
• Molecular Mass: 178.1846
• Monoisotopic Mass: 178.06299418
• SMILES: C(=C\c1ccc(cc1)O)/C(=O)OC
• Canonical SMILES: COC(=O)/C=C/c1ccc(cc1)O
• InChI: InChI=1S/C10H10O3/c1-13-10(12)7-4-8-2-5-9(11)6-3-8/h2-7,11H,1H3/b7-4+
• InChIKey: NITWSHWHQAQBAW-QPJJXVBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 3-(4-hydroxyphenyl)prop-2-enoate; methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
• IUPAC Traditional name: methyl 3-(4-hydroxyphenyl)prop-2-enoate; methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate; O-methyl-p-coumaric acid
• Synonyms: Methyl 4-hydroxycinnamate; Methyl 3-(4-hydroxyphenyl)acrylate; Methyl 4-hydroxycinnamate; Methyl 4-Hydroxy Cinnamate; (2E)-3-(4-Hydroxyphenyl)-2-propenoic Acid Methyl Ester; (E)-p-Hydroxycinnamic Acid Methyl Ester; (E)-4-Hydroxycinnamic Acid Methyl Ester; (E)-Methyl p-Hydroxycinnamate; Methyl p-Hydroxy-trans-cinnamate; Methyl trans-p-Coumarate; trans-Methyl p-Hydroxycinnamate; trans-p-Coumaric Acid Methyl Ester

Database IDs

• CAS Number: 3943-97-3; 19367-38-5
• MDL Number: MFCD00157167
• PubChem SID: 162048976
• PubChem CID: 5319562

CALCULATED PROPERTIES

• Acid pKa: 9.398705
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.2116938
• LogD (pH = 7.4): 2.20744
• Log P: 2.2117484
• Molar Refractivity: 49.8099 cm^3
• Polarizability: 18.893393 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White to Pale Orange Solid; Powder
• Melting Point: 138-140°C; 144 - 145 °C; 144-145°C

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT; Irritant
• TSCA Listed: false

Product Information

• Purity: >95%; 95+%

DETAILS

Toronto Research Chemicals - M312595

Cinnamic acid derivative used in structure-antifungal activity relationship study against Aspergillus flavus, Aspergillus terreus, and Aspergillus niger. An antifungal agent.

REFERENCES

• Bisagno, F., et al.: J. Agric. Food Chem., 55, 10645 (2007)