Hinokitiol

Hinokitiol^[1]

Names
IUPAC name 2-Hydroxy-6-propan-2-ylcyclohepta-2,4,6-trien-1-one
Other names β-Thujaplicin; 4-Isopropyltropolone
Identifiers
CAS Number	499-44-5
3D model (Jmol)	Interactive image
ChEBI	CHEBI:10447
ChEMBL	ChEMBL48310
ChemSpider	3485
ECHA InfoCard	100.007.165
KEGG	D04876
PubChem	3611
InChI 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 InChI=1/C10H12O2/c1-7(2)8-4-3-5-9(11)10(12)6-8/h3-7H,1-2H3,(H,11,12) Key: FUWUEFKEXZQKKA-UHFFFAOYAT
SMILES O=C1/C=C(\C=C/C=C1/O)C(C)C
Properties
Chemical formula	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

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. doi:10.1139/W08-161. PMID 19483786.
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. doi:10.1128/AAC.49.6.2519-2521.2005. PMC 1140513. PMID 15917561.
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.