Tectol

Tectol
Names
IUPAC name
5-(6-Hydroxy-2,2-dimethylbenzo[h]chromen-5-yl)-2,2-dimethylbenzo[h]chromen-6-ol[1]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C30H26O4/c1-29(2)15-13-21-23(25(31)17-9-5-7-11-19(17)27(21)33-29)24-22-14-16-30(3,4)34-28(22)20-12-8-6-10-18(20)26(24)32/h5-16,31-32H,1-4H3
    Key: FVTJXDIACKJEPH-UHFFFAOYSA-N
  • CC1(C=CC2=C(O1)C3=CC=CC=C3C(=C2C4=C(C5=CC=CC=C5C6=C4C=CC(O6)(C)C)O)O)C
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).

Tectol is a naturally occurring polycyclic phenolic compound first isolated from the heartwood of teak (Tectona grandis).[2] It is one of several quinonoid-related extractives present in teak heartwood and has also been reported from other plant species, including Lippia sidoides.[3]

Properties

The compound occurs together with other compounds such as tectoquinone, lapachol and deoxylapachol in teak heartwood, where these extractives are associated with the wood's high natural durability and resistance to biological degradation.[4][5] It was first produced with total synthesis in 2012.[6]

Laboratory studies have investigated tectol for biological activities, including antifungal, antiplasmodial and cytotoxic effects, although these findings are limited to experimental research.[7]

Black-streaked teak wood

Tectol has been proposed as a major contributor to the black-streak discoloration of teak heartwood. In oxidation experiments, tectol exhibited the greatest decrease in brightness among the isolated extractives. It was found that tectol is readily oxidized and undergoes subsequent polymerization to form the dark-colored compounds associated with black-streaked teak, although the discoloration process likely involves additional extractive components.[8]

References

  1. ^ "Tectol". PubChem. Retrieved 2026-06-25.
  2. ^ Sandermann, Wilhelm; Simatupang, Maruli H. (1964). "Über Inhaltsstoffe aus Teak (Tectona grandis L.), II. Konstitution and Synthese des Tectols und Dehydrotectols". Chemische Berichte. 97 (2): 588–597. doi:10.1002/cber.19640970240.
  3. ^ Costa, Sônia Maria O.; Lemos, Telma Leda G.; Pessoa, Otília Deusdênial L. (2001). "Chemical Constituents from Lippia sidoides and Cytotoxic Activity". Journal of Natural Products. 64 (6): 792–795. Bibcode:2001JNAtP..64..792C. doi:10.1021/np0005917. PMID 11421746.
  4. ^ De Castro, V. R.; Surdi, P. G.; Fernandes, S. A. (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. PMID 36323840.
  5. ^ Asdaq, Syed Mohammed Basheeruddin; Nayeem, Naira; Alam, Md. Tauquir (2022). "Tectona grandis L.f: A comprehensive review on its patents, chemical constituents, and biological activities". Saudi Journal of Biological Sciences. 29 (3): 1456–1464. Bibcode:2022SJBS...29.1456A. doi:10.1016/j.sjbs.2021.11.026. PMC 8913375. PMID 35280534.
  6. ^ Cadelis, Melissa; Barker, David; Copp, Brent (2012-11-13). "Synthesis of Hemitectol, Tectol, and Tecomaquinone I". Synlett. 23 (20): 2939–2942. doi:10.1055/s-0032-1317541. ISSN 0936-5214. Retrieved 2026-06-27.
  7. ^ Asdaq, Syed Mohammed Basheeruddin; Nayeem, Naira; Alam, Md. Tauquir (2022). "Tectona grandis L.f: A comprehensive review on its patents, chemical constituents, and biological activities". Saudi Journal of Biological Sciences. 29 (3): 1456–1464. Bibcode:2022SJBS...29.1456A. doi:10.1016/j.sjbs.2021.11.026. PMC 8913375. PMID 35280534.
  8. ^ Lukmandaru, Ganis; Ashitani, Tatsuya; Takahashi, Koetsu (2023-04-04). "Discolored Components from the Black-streaked Heartwood Extracts of Teak". Wood Research Journal. 12 (2). Masyarakat Peneliti Kayu Indonesia: 46–52. doi:10.51850/wrj.2021.12.2.46-52. ISSN 2774-9320.

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