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

• ChemBase ID: 23551
• Molecular Formular: C10H10O3
• Molecular Mass: 178.1846
• Monoisotopic Mass: 178.06299418
• SMILES: C(=O)(/C=C/c1ccc(cc1)OC)O
• Canonical SMILES: COc1ccc(cc1)/C=C/C(=O)O
• InChI: InChI=1S/C10H10O3/c1-13-9-5-2-8(3-6-9)4-7-10(11)12/h2-7H,1H3,(H,11,12)/b7-4+
• InChIKey: AFDXODALSZRGIH-QPJJXVBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(4-methoxyphenyl)prop-2-enoic acid; (2E)-3-(4-methoxyphenyl)prop-2-enoic acid
• IUPAC Traditional name: p-methoxy-cinnamic acid; P-hydroxy methyl cinnamate; p-methoxycinnamate; cinnamic acid, P-methoxy-
• Synonyms: (E)-3-(4-methoxyphenyl)acrylic acid; 4-Methoxycinnamic acid; 4-Methoxycinnamic acid, predominantly trans; 4-Methoxycinnamic acid, predominantly trans 98%; 3-(4-Methoxyphenyl)acrylic acid; (E)-3-(4-Methoxyphenyl)-2-propenoic acid; p-METHOXYCINNAMIC ACID; trans-3-(4-Methoxyphenyl)acrylic acid; 4-METHOXYCINNAMIC ACID; 3-(4-Methoxyphenyl)-2-propenoic Acid; p-Methoxycinnamic Acid; 4'-Methoxycinnamic Acid; Bernel Hydro; NSC 5303; NSC 623437; O-Methyl-p-coumaric Acid; p-MCA; trans-4-Methoxycinnamic acid; 反式-3-(4-甲氧苯基)丙烯酸; 4-甲氧基肉桂酸; 4-甲氧基肉桂酸，主要为反式; 反-4-甲氧基肉桂酸

Database IDs

• CAS Number: 943-89-5; 830-09-1
• EC Number: 212-594-0; 213-405-4
• MDL Number: MFCD00004398
• Beilstein Number: 2208397; 510468
• PubChem SID: 24896639; 160986858; 24884020
• PubChem CID: 699414

CALCULATED PROPERTIES

• Acid pKa: 4.10955
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.5737833
• LogD (pH = 7.4): -1.1144964
• Log P: 1.978415
• Molar Refractivity: 49.5231 cm^3
• Polarizability: 18.713652 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 170°C; 170-173 °C(lit.); 171-173°C; 171-175°C; 173.5 °C(lit.); 173-175°C
• Transition Temperature: crystalline phase to nematic phase 173.5 °C; nematic phase to isotropic phase 190 °C

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT; Irritant
• RTECS: UD3391300
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-37; 26-37/39
• TSCA Listed: false; 是
• 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

Product Information

• Purity: ~98%; ≥98.0% (GC); 95+%; 98%; 99%
• Linear Formula: CH3OC6H4CH=CHCO2H
• Empirical Formula (Hill Notation): C10H10O3
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 02151624

Purity: ~98%

MP Biomedicals - 05205417

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 65420

Packaging
10 g in glass bottle

Sigma Aldrich - M13807

Packaging
25, 100 g in poly bottle
5 g in glass bottle

Toronto Research Chemicals - M262150

p-MCA exerted antihyperglycemic/hypoglycemic effect by stimulating insulin secretion from pancreas and could be developed into a new potential for therapeutic agent used in type 2 diabetic patients.

REFERENCES

• Liu, I., et al.: Br. J. Pharmacol., 129, 631 (2000)
• Kim, S., et al.: Br. J. Pharmacol., 135, 1281 (2000)
• Nomura, E., et al.: Bioorg. Med. Chem., 11, 3807 (2000)
• Chiriac, C., et al.: Molecules, 10, 481 (2000)
• Jung, U., et al.: J. Pharmacol. Exp. Ther.,