(2E)-3-(3,4-dihydroxyphenyl)(1,2,3-13C3)prop-2-enoic acid

• ChemBase ID: 163525
• Molecular Formular: C9H8O4
• Molecular Mass: 183.13538451
• Monoisotopic Mass: 183.05232325
• SMILES: c1c(c(cc(c1)/[13CH]=[13CH]/[13C](=O)O)O)O
• Canonical SMILES: O[13C](=O)/[13CH]=[13CH]/c1ccc(c(c1)O)O
• InChI: InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+/i2+1,4+1,9+1
• InChIKey: QAIPRVGONGVQAS-JDWYZSDHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-3-(3,4-dihydroxyphenyl)(1,2,3-^1^3C₃)prop-2-enoic acid
• IUPAC Traditional name: (2E)-3-(3,4-dihydroxyphenyl)(1,2,3-^1^3C₃)prop-2-enoic acid
• Synonyms: 3-(3,4-Dihydroxyphenyl)-2-propenoic Acid-13C3; 3,4-Dihydroxycinnamic Acid-13C3; 3,4-Dihydroxybenzeneacrylic Acid-13C3; 4-(2-Carboxyethenyl)-1,2-dihydroxybenzene-13C3; NSC 57197-13C3; Caffeic Acid-13C3

Database IDs

• CAS Number: 1185245-82-2
• PubChem SID: 162257660
• PubChem CID: 46780148

CALCULATED PROPERTIES

• Acid pKa: 3.64384
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.32416362
• LogD (pH = 7.4): -1.8039718
• Log P: 1.5289556
• Molar Refractivity: 47.0217 cm^3
• Polarizability: 17.452097 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Bluish Green Solid
• Melting Point: >185°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C080002

Constituent of plants, probably occurs in plants only in conjugated forms.

REFERENCES

• Neish, et al.: Can. J. Biochem Physiol., 37, 1431 (1959)
• Krasemann, et al.: Arch. Pharm., et al.: 293, 721 (1959)
• Wolfrom, et al.: J. Agric. Food Chem., 8, 58 (1959)