Zingerone

One of three molecules for this week
November 21, 2011
Image of Gingerol, Shogaol, and Zingerone 3D Image of Gingerol, Shogaol, and Zingerone
Figure 1: Gingerol
Image of Gingerol, Shogaol, and Zingerone 3D Image of Gingerol, Shogaol, and Zingerone
Figure 2: Shogaol
Image of Gingerol, Shogaol, and Zingerone 3D Image of Gingerol, Shogaol, and Zingerone
Figure 3: Zingerone

Gingerol (correctly, [6]-gingerol) is the predominant phenol and most important of the pungent constituents in ginger oil. It was isolated by J. C. Thresh in 1879 from the rhizome of the ginger plant (Zingiber officinale). It and its dehydrated analogue [6]-shogaol are the primary ginger-derived bioactive compounds. Shogaol and the fragmented molecule zingerone are produced when fresh ginger is heated or cooked. A recently synthesized azagingerol analogue increases metabolism in mice and may reduce the risk of obesity-associated diseases.

Zingerone gives ginger a "hot" taste. It's also an antioxidant, although it only weakly inhibits peroxidation of phospholipid liposomes in the presence of Fe(III) and ascorbate. Zingerone's vanillin foundation and hydrocarbon tail make it a chemical relative of eugenol and capsaicin.

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