(3E)-4-[(4S)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]but-3-en-2-one

• ChemBase ID: 170673
• Molecular Formular: C13H20O2
• Molecular Mass: 208.2967
• Monoisotopic Mass: 208.14632988
• SMILES: C1(=C(C[C@@H](CC1(C)C)O)C)/C=C/C(=O)C
• Canonical SMILES: O[C@H]1CC(=C(C(C1)(C)C)/C=C/C(=O)C)C
• InChI: InChI=1S/C13H20O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h5-6,11,15H,7-8H2,1-4H3/b6-5+/t11-/m0/s1
• InChIKey: HFRZSVYKDDZRQY-QRGHLMKCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3E)-4-[(4S)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]but-3-en-2-one
• IUPAC Traditional name: (3E)-4-[(4S)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]but-3-en-2-one
• Synonyms: (3E)-4-[(4S)-4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl]-3-buten-2-one; [S-(E)]-4-(4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one; (3S)-3-Hydroxy-β-ionone

Database IDs

• CAS Number: 76739-82-7
• PubChem SID: 164226583
• PubChem CID: 10846059

CALCULATED PROPERTIES

• Acid pKa: 18.907213
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.888905
• LogD (pH = 7.4): 1.8889052
• Log P: 1.8889052
• Molar Refractivity: 63.4916 cm^3
• Polarizability: 24.15553 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H943530

A naturally occurring apocaratenoid that is produced from (3S)-β-Cryptoxanthin (C827505) by oxidative cleavage catalyzed by the caratenoid cleavage oxygenase RdCCD1.

REFERENCES

• Machida, K. et al.: Phytochem., 41, 1333 (1996)
• Schwartz, S.H. et al.: J. Biol. Chem., 276, 25208 (1996)