(2Z,4E)-5-[(1S)-1-hydroxy-2-(2H3)methyl-6,6-dimethyl-4-oxo(2H3)cyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid

• ChemBase ID: 158818
• Molecular Formular: C15H20O4
• Molecular Mass: 264.3169
• Monoisotopic Mass: 264.13615912
• SMILES: C1(CC(=O)C=C([C@]1(O)/C=C/C(=C\C(=O)O)/C)C)(C)C
• Canonical SMILES: OC(=O)/C=C(\C=C\[C@@]1(O)C(=CC(=O)CC1(C)C)C)/C
• InChI: InChI=1S/C15H20O4/c1-10(7-13(17)18)5-6-15(19)11(2)8-12(16)9-14(15,3)4/h5-8,19H,9H2,1-4H3,(H,17,18)/b6-5+,10-7-/t15-/m1/s1
• InChIKey: JLIDBLDQVAYHNE-YKALOCIXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z,4E)-5-[(1S)-1-hydroxy-2-(^2H₃)methyl-6,6-dimethyl-4-oxo(^2H₃)cyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid
• IUPAC Traditional name: (2Z,4E)-5-[(1S)-1-hydroxy-2-(^2H₃)methyl-6,6-dimethyl-4-oxo(^2H₃)cyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid
• Synonyms: [S-(Z,E)]-5-[1-Hydroxy-6,6-dimethyl-2-(methyl-d6)-4-oxo-2-cyclohexen-1-yl]-3-methyl-2,4-pentadienoic Acid; S-ABA-d6; Dormin-d6; (+)-cis,trans-Abscisic Acid-d6

Database IDs

• PubChem SID: 162252953
• PubChem CID: 46779839

CALCULATED PROPERTIES

• Acid pKa: 4.7381496
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.2628527
• LogD (pH = 7.4): -0.5142804
• Log P: 2.0932755
• Molar Refractivity: 74.9764 cm^3
• Polarizability: 28.11777 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 159-161°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, amber vial

DETAILS

Toronto Research Chemicals - A110002

The natural isomer of the abscission-accelerating plant hormone.

REFERENCES

• Krochko, J.E., et al.: Plant Physiol., 118, 849 (1998)
• Jacobsen, J.V., et al.: Psysiol. Plant., 115, 428 (1998)