Taxodone

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title: "Taxodone" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["quinone-methides", "tertiary-alcohols", "diterpenes", "phenanthrenes", "enols", "secondary-alcohols", "diols", "isopropyl-compounds", "hydroxy-ketones"] topic_path: "general/quinone-methides" source: "https://en.wikipedia.org/wiki/Taxodone" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Watchedfields = changed | verifiedrevid = 461825977 | Name = Taxodone | ImageFile = Taxodone.png | ImageSize = | ImageAlt = Taxodone | ImageFile1 = Taxodone Ball.png | ImageSize1 = | ImageAlt1 = Taxodone 3d | IUPACName = 6α,11-Dihydroxyabieta-7,9(11),13-trien-12-one | SystematicName = (4bS,8aS,9S)-4,9-Dihydroxy-4b,8,8-trimethyl-2-(propan-2-yl)-5,6,7,8,8a,9-hexahydrophenanthren-3(4bH)-one | OtherNames = NSC122420, AC1L9XIL, CID457961 | Section1 = {{Chembox Identifiers | CASNo_Ref = | CASNo = 19039-02-2 | PubChem = 275528 | ChemSpiderID_Ref = | ChemSpiderID = 242416 | SMILES = O=C1\C(=C/C=2/C(=C1/O)[C@]3(C)C@@HC(C)(C)CCC3)C(C)C | InChI = 1/C20H28O3/c1-11(2)13-9-12-10-14(21)18-19(3,4)7-6-8-20(18,5)15(12)17(23)16(13)22/h9-11,14,18,21,23H,6-8H2,1-5H3/t14-,18-,20+/m0/s1 | InChIKey = QEAIMIKGLGBTSA-ADLFWFRXBH | StdInChI_Ref = | StdInChI = 1S/C20H28O3/c1-11(2)13-9-12-10-14(21)18-19(3,4)7-6-8-20(18,5)15(12)17(23)16(13)22/h9-11,14,18,21,23H,6-8H2,1-5H3/t14-,18-,20+/m0/s1 | StdInChIKey_Ref = | StdInChIKey = QEAIMIKGLGBTSA-ADLFWFRXSA-N | Section2 = {{Chembox Properties | C = 20| H = 28 | O = 3 | Appearance = Golden crystalline solid | MeltingPtC = 176 to 177 | Solubility = Insoluble | SolubleOther = Soluble | Solvent = chloroform, alcohol, hexane, ether}} | Section8 = {{Chembox Related | OtherCompounds = Taxodione

Taxodone is a naturally occurring diterpenoid found in Taxodium distichum (bald cypress), Rosmarinus officinalis (rosemary), several salvia species and other plants, along with its oxidized rearrangement product, taxodione. Taxodone and taxodione exhibit anticancer, antibacterial, antioxidant, antifungal, insecticide, and antifeedant activities.

Discovery

Taxodone was first isolated in 1968 from the seeds of Taxodium distichum (Bald Cypress) by S. Morris Kupchan and coworkers. Taxodone occurs naturally in the form of (+)-taxodone.

Occurrence

Taxodone and/or taxodione have been identified in several plants besides Taxodium distichum including: Rosmarinus officinalis (Rosemary), Salvia barrelieri, Salvia moorcroftiana, Salvia staminea, Salvia clevelandii (Cleveland Sage), Salvia hypargeia, Salvia montbretii, Salvia nipponica, Salvia verbenaca (Wild Clary), Salvia lanigera, Salvia prionitis, Salvia deserta, Salvia phlomoides, and Plectranthus hereroensis

Taxodone, taxodione and their reaction products have been used as archeological and geological biomarkers.

Analogs of taxodone and taxodione have also been isolated. 2-hydroxy taxodone and 2-hydroxy-taxodione have been found in Salvia texana (Texas Sage). 5,6-Didehydro-7-hydroxy-taxodone was found in Salvia munzii. 7-Hydroxytaxodione, 7,7‘-bistaxodione, and 11,11‘-didehydroxy-7,7‘-dihydroxytaxodione were found in Salvia montbretti.

Activity

Taxodone and taxodione possess in vivo activity against Walker intramuscular carcinosarcoma 256 in rats (25 and 40 mg/kg, respectively) and in vitro activity against cells derived from human carcinoma of the nasopharynx (KB) (ED50 = 0.6 and 3 ug/ml respectively). Taxodione may have potential in treatment of cardiovascular disease.

The use of taxodone and taxodione to inhibit hair growth has been patented. Treatment of benign prostate enlargement with taxodone has also been patented.

Chemistry

Taxodone was the first isolated example of a quinone methide with a labile hydrogen adjacent to this reactive chromophore. Kupchan demonstrated that taxodone aromatizes to a catechol ketone upon exposure to mild acid. Air oxidation of this catechol ketone affords taxodione.

::figure[src="https://upload.wikimedia.org/wikipedia/commons/7/73/Taxodone-to-taxodione.png"] ::

Synthesis

Taxodone rearranges easily in the presence of mild acids and reacts readily with nucleophiles. Although taxodone shows higher anticancer and antibacterial activity than taxodione it eluded creation in the laboratory for over 25 years because of its inherent instability. During this time several different groups reported syntheses of the more stable taxodione.

In 1993 taxodone was synthesized for the first time in a 16 step sequence utilizing a unique phenol benzylic epoxide electron reorganization in the final step. As taxodone readily decomposes into taxodione this synthesis of taxodone also constitutes a formal synthesis of taxodione as well.

::figure[src="https://upload.wikimedia.org/wikipedia/commons/d/d6/Taxodone_synth_ACS.png"] ::

Since the synthesis of taxodone there have been additional syntheses of taxodione and analogs.

References

References

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quinone-methidestertiary-alcoholsditerpenesphenanthrenesenolssecondary-alcoholsdiolsisopropyl-compoundshydroxy-ketones