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Pogostone

molecular structure of pogostone

INCI name: patchouli oil
Synonyms: dhelwangin
Molecular formula: C12H16O4
Molecular weight: 224.26 g/mol
IUPAC name: 4-hydroxy-6-methyl-3-(4-methylpentanoyl)pyran-2-one
CAS number: 23800-56-8

Pogostone is one of the key components of patchouli oil, which is the essential oil of the aerial part (Pogostemonis herba) of the herbaceous plant, Pogostemon cablin (Blanco) Benth. In terms of its chemical characterization, pogostone is a pyranone—a pyran ring containing a ketone functional group. It is used in traditional Chinese and Indian (Ayurveda) medicine to treat a variety of ailments and symptoms including dampness, diarrhea, dermatitis, fever, and vomiting as well as to help stimulate appetite.1 Curiously, pogostone also has insect repellant properties.

In the last couple of years, several studies were conducted seaking to elucidate to protective effects of pogostone and patchouli oil against UV-induced photoaging.2,3 It should be noted that these studies were carried out with mice in an effort to elucidate the benefits from a histological and biochemical point of view. Overall, histological results look promising, while the measured levels of antioxidants in skin appear less effected by UV radiation in pogostone-treated skin as compared to a control. In addition, a number of inflammatory cytokines and matrix metalloproteinases that degrade structural properties of dermal matrix were down regulated as a result of pogostone treatment.2

Properties
Melting point: 41 - 41.6 °C4
Solubility: 0.39 g/L (ALOGPS)4
Log P: 1.6 (ALOGPS)4

References
1. R. Murugan and C. Livingstone, Origin of the name ‘patchouli’ and its history, Curr. Sci., 99, 1274-1276 (2010).
2. X.F. Wang, Y.F. Huang, L. Wang, L.Q. Xu, X.T. Yu, Y.H. Liu, C.L. Li, J.Y. Zhan, Z.R. Su, J.N. Chen, and H.F. Zeng, Photo-protective activity of pogostone against UV-induced skin premature aging in mice, Exp. Gerontol., 77, 76-86 (2016).
3. R.F. Lin, X.X. Feng, C.W. Li, X.J. Zhang, X.T. Yu, J.Y. Zhou, X. Zhang, Y.L. Xie, Z.R. Su, and J.Y. Zhan, Prevention of UV radiation-induced cutaneous photoaging in mice by topical administration of patchouli oil, J. Ethnopharmacol., 154, 408-418 (2014).
4. Human Metabolome Database (HMDB), www.hmdb.ca/metabolites/HMDB0030703.