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Practical synthesis of naringenin

Posted on 26. August, 2015.

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Flavanones, 2-phenylchroman-4-ones, belong to the family of flavonoids, many of which are produced as secondary metabolites in the plant kingdom and exhibit a broad spectrum of interesting biological activities. Naringenin (5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one) is one of the most abundant flavanones present in grapefruits and citrus fruits. It is well-known for its beneficial health-related properties, including anti-oxidant, anti-cancer, anti-atherogenic, antiinflammatory and anti-proliferative activities.

Naringenin is reported to inhibit the assembly and long-term production of infectious hepatitis C virus particles in a dose-dependent manner. Furthermore, naringenin potentiates intracellular signalling responses to low insulin doses, suggesting that naringenin sensitises hepatocytes to insulin.
Naringenin has also been shown to traverse the blood–brain barrier and exert a diverse array of neuronal effects through their ability to interact with the protein kinase C (PKC) signalling pathways.

In this article, the authors now report the preparation of naringenin using commercially available starting materials, and by an improved procedure with satisfactory yields.

Read the full article in  Journal of Chemical Research, Volume 39, Number 8, August 2015, pp. 455-457.

Keywords: naringenin, taxicatigenin, anisaldehyde, p-methoxycinnamic acid, chalcone

Authors: Qian Wanga, Jian Yanga*, Xiang-ming Zhangb,c, Lei Zhoub,c, Xia-li Liaoa and Bo Yanga

aFaculty of Life Science and Technology, Kunming University of Science and Technology, 727 South Jingming Road, Chenggong District, Kunming, Yunnan Province 650500, P.R. China
bCollege of Pharmacy, Nankai University, 94 WeiJin Road, Nankai District, Tianjing 300071, P.R. China
cTianjin International Joint Academy of Biomedicine, 220 Dongting Road, Tianjin economic and technological development zone, Tianjin 300457, P.R. China