Thujaplicin

Thujaplicin

α-Thujaplicin

β-Thujaplicin (hinokitiol)

γ-Thujaplicin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
EC Number
  • β: 207-880-7
UNII
  • α: InChI=1S/C10H12O2/c1-7(2)8-5-3-4-6-9(11)10(8)12/h3-7H,1-2H3,(H,11,12)
    Key: TUFYVOCKVJOUIR-UHFFFAOYSA-N
  • β: InChI=1S/C10H12O2/c1-7(2)8-4-3-5-9(11)10(12)6-8/h3-7H,1-2H3,(H,11,12)
    Key: FUWUEFKEXZQKKA-UHFFFAOYSA-N
  • γ: InChI=1S/C10H12O2/c1-7(2)8-3-5-9(11)10(12)6-4-8/h3-7H,1-2H3,(H,11,12)
    Key: WKEWHSLZDDZONF-UHFFFAOYSA-N
  • α: CC(C)C1=C(C(=O)C=CC=C1)O
  • β: CC(C)C1=CC(=O)C(=CC=C1)O
  • γ: CC(C)C1=CC=C(C(=O)C=C1)O
Properties
C10H12O2
Molar mass 164.204 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Thujaplicin (isopropyl cycloheptatrienolone) is any of three isomeric tropolone-related natural products that have been isolated from the softwoods of the trees of Cupressaceae family.[1] These compounds are known for their antibacterial, antifungal, and antioxidant properties.[2][3] They were the first natural tropolones to be made synthetically.[4]

  1. ^ ERDTMAN, HOLGER; GRIPENBERG, JARL (May 1948). "Antibiotic Substances from the Heart Wood of Thuja plicata Don". Nature. 161 (4097): 719. Bibcode:1948Natur.161..719E. doi:10.1038/161719a0. PMID 18860272. S2CID 4074514.
  2. ^ Chedgy, Russell J.; Lim, Young Woon; Breuil, Colette (May 2009). "Effects of leaching on fungal growth and decay of western redcedar". Canadian Journal of Microbiology. 55 (5): 578–586. doi:10.1139/W08-161. PMID 19483786.
  3. ^ Chedgy, R. (2010). Secondary Metabolites of Western Red Cedar (Thuja plicata). Lambert Academic Publishing. ISBN 978-3-8383-4661-8.
  4. ^ Cook, J. W.; Raphael, R. A.; Scott, A. I. (1951). "149. Tropolones. Part II. The synthesis of α-, β-, and γ-thujaplicins". J. Chem. Soc.: 695–698. doi:10.1039/JR9510000695.