Pogostone
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| Preferred IUPAC name
4-hydroxy-6-methyl-3-(4-methylpentanoyl)pyran-2-one | |
| Other names
Dhelwangin
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C12H16O4 | |
| Molar mass | 224.256 g·mol−1 |
| Appearance | Colorless needles |
| Melting point | 32–33 °C (90–91 °F; 305–306 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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Pogostone or dhelwangin is a naturally occurring organic compound with the formula C12H16O4. Classified as a secondary metabolite, primarily found in patchouli, a member of the mint family Lamiaceae.[1] This plant has historically been used in traditional Chinese medicine to treat ailments such as the common cold, nausea, diarrhea, headache, and fever,[2] and is also applied for its antifungal properties.[3] Pogostone was first identified in 1969 as the major antimicrobial constituent of Pogostemonis Herba, the dried aerial parts of patchouli used in herbal preparations.[4]
Structure and properties
[edit | edit source]Pogostone has the molecular formula C12H16O4.[1][5] Pogostone (PO) was obtained as needle-like colorless crystals.[5] Its melting point was reported as 32–33 °C.[5] It features a 2H-pyranone core and was first structurally characterized by X-ray crystallography, which also revealed the presence of intramolecular hydrogen bonding.[5]
Due to its low natural abundance in the plant, synthetic methods for pogostone production have been developed.[1] One synthetic route involves the condensation of dehydroacetic acid (DHA) with aldehydes in dry tetrahydrofuran (THF) under nitrogen at low temperature (0–5 °C), followed by hydrogenation, chromatography, and crystallization.[1][5] The reaction proceeds via deprotonation, Michael addition reaction, tautomerization, and further deprotonation steps.[5] Two diastereomeric dimers of pogostone, with (8S,9R) and (8S,9S) configurations, have also been synthesized and structurally confirmed by nuclear magnetic resonance and X-ray diffraction.[5]
Applications
[edit | edit source]The development of synthetic routes for pogostone and its analogues facilitates their potential application as novel antifungal agents, particularly in the treatment of azole-resistant Candida albicans infections.[1] Its anti-inflammatory activity also supports further exploration as a therapeutic agent for conditions such as septic shock.[6] However, its inhibitory effects on major cytochrome P450 enzymes warrant caution and further study regarding possible drug–drug interactions.[7]
References
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