(2E)-2-methyl(4,4,4-2H3)but-2-enoic acid

• ChemBase ID: 178644
• Molecular Formular: C5H8O2
• Molecular Mass: 100.11582
• Monoisotopic Mass: 100.0524295
• SMILES: C(=C\C)(\C)/C(=O)O
• Canonical SMILES: C/C(=C\C)/C(=O)O
• InChI: InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)/b4-3+
• InChIKey: UIERETOOQGIECD-ONEGZZNKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-2-methyl(4,4,4-^2H₃)but-2-enoic acid
• IUPAC Traditional name: (2E)-2-methyl(4,4,4-^2H₃)but-2-enoic acid
• Synonyms: (2E)-2-Methyl-2-butenoic Acid; (E)-2-Methylcrotonic Acid; (E)-2,3-Dimethylacrylic Acid; (E)-2-Methyl-2-butenoic acid; (E)-α-Methylcrotonic acid; Cevadic Acid; NSC 44235; NSC 8999; Tiglinic Acid; trans-2,3-Dimethylacrylic Acid; trans-2-Methyl-2-butenoic Acid; trans-2-Methylcrotonic Acid; trans-α,β-Dimethylacrylic Acid; Tiglic Acid-d3

Database IDs

• CAS Number: 19146-57-7
• PubChem SID: 164234554
• PubChem CID: 45040533

CALCULATED PROPERTIES

• Acid pKa: 4.9713354
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.67428637
• LogD (pH = 7.4): -1.0820109
• Log P: 1.3151327
• Molar Refractivity: 27.322 cm^3
• Polarizability: 10.226851 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: Off-White to Yellow Solid
• Melting Point: 58-61°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - T440052

Labelled Tiglic acid (T440050). Tiglic acid is the stable isomer of angelic acid. Tiglic acid was found as glyceride in croton oil, as butyl ester in the oil of the Roman camomile, and as geranyl tiglate in oil of geranium. Tiglic acid is formed during th

REFERENCES

• Bueding, et al.: J. Biol. Chem., 202, 505 (1953)