Tectol
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| IUPAC name
5-(6-Hydroxy-2,2-dimethylbenzo[h]chromen-5-yl)-2,2-dimethylbenzo[h]chromen-6-ol[1]
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3D model (JSmol)
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| ECHA InfoCard | Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). |
| E number | Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C30H26O4 | |
| Molar mass | 450.534 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Tectol is a naturally occurring polycyclic phenolic compound isolated primarily from the heartwood of teak (Tectona grandis)[2] and also reported from other plant species including the species, Lippia sidoides.[3]
It belongs to a group of quinonoid and lignan-related natural products associated with the durability, coloration, and biological resistance of teak heartwood.[4]
Chemistry and occurrence
Tectol has the molecular formula C30H26O4 and a molecular weight of 450.53 g/mol.[1][5] It is structurally related to other teak extractives including tectoquinone, lapachol, deoxylapachol, and dehydrotectol.[4][6]
The compound has been described as a dimeric benzochromene-type natural product and is part of a broader class of oxygenated polycyclic phenolic compounds found in durable hardwood species.[7]
Tectol has been identified in solvent extracts of teak heartwood and sawdust, particularly in chloroform, hexane, and ethyl acetate fractions.[2]
Teak heartwood contains a complex mixture of quinones and phenolic compounds associated with its natural resistance to fungi and xylophagous insects.[8] Among these compounds, tectol occurs alongside tectoquinone, deoxylapachol, and related naphthoquinones.[9]
Role
The durability of teak wood is widely attributed to the presence of heartwood extractives exhibiting antifungal and anti-termite activity.[4] Tectol has been isolated from fractions showing inhibitory effects against wood-decaying fungi and is considered one of several compounds contributing to teak's superior biological resistance.[2]
Studies of teak extractives indicate that quinone-type compounds, including tectol, contribute to the natural defense mechanisms of heartwood against microbial degradation.[8]
Oxidative behaviour and discoloration
Research on black-streaked teak heartwood has shown that several extractive compounds undergo oxidative transformations that contribute to dark coloration patterns in wood.[7]
Experimental studies have indicated that tectol exhibits oxidation-dependent colour changes and may participate in the formation of dark streaks in teak veneer and heartwood.[7] However, wood discoloration is considered a complex process involving multiple phenolic and quinonoid constituents rather than a single pigment.[4]
Biological activity
Tectol has demonstrated biological activity in laboratory studies. It has been reported as an inhibitor of farnesyltransferase[10] and has shown activity against the protozoan parasite Plasmodium falciparum in vitro.[5]
The compound has also been investigated for cytotoxic effects[3] against human cancer cell lines, suggesting potential pharmacological relevance of teak-derived quinonoid compounds.[7][9]
Related compounds
Tectol is one of several bioactive extractives identified in teak heartwood, including:
- Tectoquinone
- Lapachol
- Deoxylapachol
- Dehydrotectol
These compounds collectively contribute to the natural durability and characteristic coloration of teak wood.[4]
References
- ↑ 1.0 1.1 "Tectol". PubChem. Retrieved 2026-06-25.
- ↑ 2.0 2.1 2.2 Sumthong, Pattarawadee; Romero-González, Roman R.; Verpoorte, Robert (2008). "Identification of Anti-Wood Rot Compounds in Teak (Tectona grandis L.f.) Sawdust Extract". Journal of Wood Chemistry and Technology. 28 (4): 247–260. doi:10.1080/02773810802452592.
- ↑ 3.0 3.1 Costa, Sônia Maria O.; Lemos, Telma Leda G.; Pessoa, Otília Deusdênial L.; Pessoa, Claudia; Montenegro, Raquel C.; Braz-Filho, Raimundo (2001-06-01). "Chemical Constituents from Lippia sidoides and Cytotoxic Activity". Journal of Natural Products. 64 (6): 792–795. doi:10.1021/np0005917. ISSN 0163-3864.
- ↑ 4.0 4.1 4.2 4.3 4.4 De Castro, V. R.; Surdi, P. G.; Fernandes, S. A.; Da Silva Berger, M.; Vinha Zanuncio, A. J.; Zanuncio, J. C.; De Oliveira Araujo, S. (2022). "Chemical composition of heartwood and sapwood of Tectona grandis characterized by CG/MS-PY". Scientific Reports. 12 (1): 18441. Bibcode:2022NatSR..1218441D. doi:10.1038/s41598-022-22800-1. PMC 9630424 Check
|pmc=value (help). PMID 36323840 Check|pmid=value (help). - ↑ 5.0 5.1 "Tectol". glpbio.com.
- ↑ Asdaq, Syed Mohammed Basheeruddin; Nayeem, Naira; Alam, Md. Tauquir; Alaqel, Saleh I.; Imran, Mohd.; Hassan, El-Waleed Elamin; Rabbani, Syed Imam (2022). "Tectona grandis L.f: A comprehensive review on its patents, chemical constituents, and biological activities". Saudi Journal of Biological Sciences. Elsevier BV. 29 (3): 1456–1464. doi:10.1016/j.sjbs.2021.11.026. ISSN 1319-562X.
- ↑ 7.0 7.1 7.2 7.3 "Phenolic constituents of teak heartwood and their properties". Arabian Journal of Chemistry. 2021. doi:10.1016/j.arabjc.2021.103359.
- ↑ 8.0 8.1 "Variations in natural durability and extractive composition of teak (Tectona grandis) wood". Annals of Forest Science. 2009. doi:10.1051/forest/2009051.
- ↑ 9.0 9.1 "An In-depth Technical Guide to the Chemical Structure and Synthesis of Tectol" (PDF). Retrieved 2026-06-25.
- ↑ Cadelis, Melissa M.; Bourguet-Kondracki, Marie-Lise; Dubois, Joëlle; Valentin, Alexis; Barker, David; Copp, Brent R. (2016). "Discovery and preliminary structure–activity relationship studies on tecomaquinone I and tectol as novel farnesyltransferase and plasmodial inhibitors". Bioorganic & Medicinal Chemistry. Elsevier BV. 24 (14): 3102–3107. doi:10.1016/j.bmc.2016.05.024. ISSN 0968-0896.
External links
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