Hinokitiol

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Hinokitiol[1]
Skeletal formula of hinokitiol
Ball-and-stick model of the hinokitiol molecule
Names
IUPAC name
2-Hydroxy-6-propan-2-ylcyclohepta-2,4,6-trien-1-one
Other names
β-Thujaplicin; 4-Isopropyltropolone
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.165
KEGG
Properties
C10H12O2
Molar mass 164.20 g·mol−1
Appearance Colorless to pale yellow crystals
Melting point 50 to 52 °C (122 to 126 °F; 323 to 325 K)
Boiling point 140 °C (284 °F; 413 K) at 10 mmHg
Hazards
Flash point 140 °C (284 °F; 413 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Hinokitiol (β-thujaplicin) is a natural monoterpenoid found in the wood of trees in the family Cupressaceae. It is a tropolone derivative and one of the thujaplicins.[2] Hinokitiol has inhibitory effects on Chlamydia trachomatis and may be clinically useful as a topical drug.[3][4]

The name originates from the fact it was originally isolated in Taiwanese hinoki in 1936.[5] It is actually almost absent in Japanese hinoki while it is contained in high concentration (about 0.04% of heartwood mass) in Juniperus cedrus, Hiba cedar wood (Thujopsis dolabrata) and Western red cedar (Thuja plicata). It can be readily extracted from the cedarwood with solvent and ultrasonication.[6]

References[edit]

  1. ^ β-Thujaplicin at Sigma-Aldrich
  2. ^ Chedgy, Russell J.; Lim, Young Woon; Breuil, Colette (2009). "Effects of leaching on fungal growth and decay of western redcedar". Canadian Journal of Microbiology. 55 (5): 578–86. PMID 19483786. doi:10.1139/W08-161. 
  3. ^ Yamano, H; Yamazaki, T; Sato, K; Shiga, S; Hagiwara, T; Ouchi, K; Kishimoto, T (2005). "In vitro inhibitory effects of hinokitiol on proliferation of Chlamydia trachomatis". Antimicrobial Agents and Chemotherapy. 49 (6): 2519–21. PMC 1140513Freely accessible. PMID 15917561. doi:10.1128/AAC.49.6.2519-2521.2005. 
  4. ^ Chedgy, Russell. Secondary metabolites of Western red cedar (Thuja plicata): their biotechnological applications and role in conferring natural durability. LAP Lambert Academic Publishing, 2010, ISBN 3-8383-4661-0, ISBN 978-3-8383-4661-8
  5. ^ Murata, I.; Itô, S.; Asao, T. (2012). "Tetsuo Nozoe: Chemistry and Life". Chem Record. 12 (6): 599–607. doi:10.1002/tcr.201200024. 
  6. ^ Chedgy, Russell J.; Daniels, C.R.; Kadla, John; Breuil, Colette (2007). "Screening fungi tolerant to Western red cedar (Thuja plicata Donn) extractives. Part 1. Mild extraction by ultrasonication and quantification of extractives by reverse-phase HPLC". Holzforschung. 61 (2): 190. doi:10.1515/HF.2007.033. 

External links[edit]