Pogostone

Pogostone

Names
Preferred IUPAC name 4-hydroxy-6-methyl-3-(4-methylpentanoyl)pyran-2-one
Other names Dhelwangin
Identifiers
CAS Number	23800-56-8
3D model (JSmol)	Interactive image
ChEBI	CHEBI:138756
ChemSpider	13415784
PubChem CID	54695756
UNII	QG8U8GA5EP
CompTox Dashboard (EPA)	DTXSID001019967
InChI InChI=1S/C12H16O4/c1-7(2)4-5-9(13)11-10(14)6-8(3)16-12(11)15/h6-7,14H,4-5H2,1-3H3 Key: AJFJTORMMHWKFW-UHFFFAOYSA-N
SMILES CC1=CC(=C(C(=O)O1)C(=O)CCC(C)C)O
Properties
Chemical formula	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). Infobox references

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

Pogostone has the molecular formula C₁₂H₁₆O₄.¹⁵ 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.¹⁵ 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

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