Hinokitiol
 | |
| Names | |
|---|---|
| IUPAC name
2-Hydroxy-6-propan-2-ylcyclohepta-2,4,6-trien-1-one | |
| Other names
β-Thujaplicin; 4-Isopropyltropolone | |
| Identifiers | |
499-44-5  | |
| ChEBI | CHEBI:10447  |
| ChEMBL | ChEMBL48310 |
| ChemSpider | 3485 |
| |
| Jmol-3D images | Image |
| KEGG | D04876 |
| PubChem | 3611 |
| |
| Properties | |
| Molecular 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 noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| verify (what is: /?) | |
| 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
- ↑ β-Thujaplicin at Sigma-Aldrich
- ↑ 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.
- ↑ 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.
- ↑ 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
- ↑ Murata, I.; Itô, S.; Asao, T. (2012). "Tetsuo Nozoe: Chemistry and Life". Chem Record 12 (6): 599–607. doi:10.1002/tcr.201200024.
- ↑ 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.