3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid

• ChemBase ID: 4762
• Molecular Formular: C10H10O4
• Molecular Mass: 194.184
• Monoisotopic Mass: 194.0579088
• SMILES: COc1ccc(cc1O)/C=C/C(=O)O
• Canonical SMILES: COc1ccc(cc1O)/C=C/C(=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+
• InChIKey: QURCVMIEKCOAJU-HWKANZROSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid; (2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid
• IUPAC Traditional name: 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid; isoferulic acid; (2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid
• Synonyms: 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid; 3-HYDROXY-4-METHOXYCINNAMIC ACID; 3-Hydroxy-4-methoxycinnamic acid, predominantly trans; (2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid; trans-3-(3-Hydroxy-4-methoxyphenyl)acrylic acid; trans-3-Hydroxy-4-methoxycinnamic acid; trans-Isoferulic acid; 3-(3-Hydroxy-4-methoxyphenyl)acrylic Acid; Isoferulic Acid; 3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic Acid; 3-Hydroxy-4-methoxycinnamic Acid (Isoferulic Acid); Hesperetic acid; Hesperetinic acid; Isoferulic acid; 3-羟基-4-甲氧基肉桂酸, 主体成分为反式; 3-羟基-4-甲氧基肉桂酸，主要为反式

Database IDs

• CAS Number: 537-73-5; 25522-33-2
• EC Number: 247-071-6; 208-676-0
• MDL Number: MFCD00004391
• Beilstein Number: 2212760
• PubChem SID: 99443580; 160968194; 24846591
• PubChem CID: 736186

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.7674725
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.058786187
• LogD (pH = 7.4): -1.6036878
• Log P: 1.6748496
• Molar Refractivity: 51.504 cm^3
• Polarizability: 19.349825 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.56
• LOG S: -2.35
• Solubility (Water): 8.71e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: Off-White to Light Beige Solid; Powder
• Melting Point: 230 °C (dec.)(lit.); 230-232°C (dec.); 230-236 °C; 231 - 233°C; ca 231°C dec.
• Hydrophobicity(logP): 1.421

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: UD3365400
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2; 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37; 26-37/39
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: Lowers plasma glucose levels

Product Information

• Purity: ≥98.0% (HPLC); 95%; 97%; 98+%
• Grade: analytical standard
• Biological Source: Isol. from Cimicifuga racemosa, Catalpa ovata and other plants
• Shelf Life: (limited shelf life, expiry date on the label)
• Application(s): Antihyperglycemic action; Shown with inhibitive effect of against Staphylococcus aureus
• Linear Formula: HOC6H3(OCH3)CH=CHCO2H
• Empirical Formula (Hill Notation): C10H10O4

DETAILS

MP Biomedicals - 05210655

MP Biomedicals Rare Chemical collection

DrugBank - DB07109

Drug information: experimental

Sigma Aldrich - 103012

Packaging
1, 5 g in glass bottle

Toronto Research Chemicals - H946180

3-Hydroxy-4-methoxycinnamic Acid (Isoferulic acid) is a hypoglycemic agent.

REFERENCES

• Liu, I.-M., et al.: J. Pharmacol. Exp. Ther., 307, 1196 (2003)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 184B; 184D, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1057C; 1058B, (nmr)
• Hermann, F.X., Pharmazie, 1956, 11, 433, (rev)
• Bate-Smith, E.C., Sci. Proc. R. Dublin Soc., 1956, 27, 165, (occur)
• Dewick, P.M. et al., Chem. Comm., 1968, 673, (biosynth)
• Swain, T. et al., Phytochemistry, 1970, 9, 2115, (biosynth)
• Achenbach, H. et al., Chem. Ber., 1971, 104, 1468, (isol, deriv)
• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, no. 957
• Desai, M.N. et al., CA, 1973, 79, 111369c, (detn, Fe)
• Bowden, B.F. et al., Aust. J. Chem., 1975, 28, 91, (derivs)
• Kelley, C.J. et al., J.O.C., 1976, 41, 449, (cmr)
• de Silva, S.O. et al., Can. J. Chem., 1979, 57, 1598, (synth, deriv)
• Garcia-Granda, S. et al., Acta Cryst. C, 1987, 43, 683, (cryst struct)
• Stuart, J.G. et al., J. Het. Chem., 1987, 24, 1589, (synth, ir, pmr, deriv)
• Blase, F.R. et al., Synth. Commun., 1995, 25, 3187, (synth, Isoferulic acid)
• Souleman, A.A.M. et al., Nat. Prod. Sci., 1998, 4, 245-252, (Isoferulic acid 3'-sulfate)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CAK375