2-hydroxy-4-(propan-2-yl)cyclohepta-2,4,6-trien-1-one

• ChemBase ID: 139976
• Molecular Formular: C10H12O2
• Molecular Mass: 164.20108
• Monoisotopic Mass: 164.08372962
• SMILES: CC(C)c1cccc(=O)c(c1)O
• Canonical SMILES: CC(c1cccc(=O)c(c1)O)C
• InChI: InChI=1S/C10H12O2/c1-7(2)8-4-3-5-9(11)10(12)6-8/h3-7H,1-2H3,(H,11,12)
• InChIKey: FUWUEFKEXZQKKA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-4-(propan-2-yl)cyclohepta-2,4,6-trien-1-one
• IUPAC Traditional name: 2-hydroxy-4-isopropylcyclohepta-2,4,6-trien-1-one; 2-hydroxy-4-(propan-2-yl)cyclohepta-2,4,6-trien-1-one
• Synonyms: beta-Thujaplicin; 2-Hydroxy-4-isopropyl-2,4,6-cycloheptatrien-1-one; Hinokitiol; β-Thujaplicin; Thujaplicin-Beta; 2-羟基-4-异丙基-2,4,6-环庚三烯-1-酮; 桧木醇; 日柏醇

Database IDs

• CAS Number: 499-44-5
• EC Number: 207-880-7
• MDL Number: MFCD00040180
• PubChem SID: 162234222; 24870612
• PubChem CID: 3611

CALCULATED PROPERTIES

• Acid pKa: 11.35299
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.0624456
• LogD (pH = 7.4): 2.062398
• Log P: 2.0624464
• Molar Refractivity: 51.5506 cm^3
• Polarizability: 18.386024 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 50-52 °C(lit.)
• Boiling Point: 140 °C/10 mmHg(lit.)

Safety Information

• RTECS: GU4200000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Mechanism of Action: Tyrosinase and carboxypeptidase A inhibitor

Product Information

• Purity: ≥99.0%; 99%
• Grade: SAJ special grade
• Biological Source: Occurs in Juniperus conferta and the heartwood of Thuja plicata . Also from Thuja occidentalis, Thuja dolabrata, Thuja standishii, Cupressus spp., and Juniperus spp.
• Application(s): Cytostatic; Phytoncide; Tuberculostatic
• Empirical Formula (Hill Notation): C10H12O2

DETAILS

Sigma Aldrich - 469521

Packaging
5 g in glass bottle

REFERENCES

• Anderson, A.B. et al., Acta Chem. Scand., 1948, 2, 644, (isol, struct)
• Tanaka, K. et al., Tetrahedron, 1971, 27, 4889, (synth)
• Derry, J.E. et al., J.C.S. Perkin 2, 1972, 694, (cryst struct)
• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, no. 573, (occur)
• Noyori, R. et al., J.O.C., 1975, 40, 806, (synth)
• Tamura, Y. et al., Tet. Lett., 1977, 4075, (synth)
• Neumann, M. et al., Tet. Lett., 1978, 5033, (synth)
• Miyashita, M. et al., J.O.C., 1987, 52, 2602, (synth)
• Banwell, M.G. et al., Aust. J. Chem., 1991, 44, 705, (synth)
• Ohishi, H. et al., Acta Cryst. C, 1994, 50, 587, (cryst struct, bibl)
• Madar, Z. et al., Phytochemistry, 1995, 38, 351, (Cupressotropolone A)
• Ono, M. et al., Biosci., Biotechnol., Biochem., 1998, 62, 1653-1659, (prodn)
• Yoshihiko, I. et al., Biol. Pharm. Bull., 1999, 22, 990-993, (activity)
• Yamaguchi, T. et al., J. Wood Sci., 1999, 45, 170-173; CA, 131, 127604, (activity)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, IRR000