Raspberry ketone

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Template:Chembox ECNumberTemplate:Chembox E number
Raspberry ketone[1]
IUPAC name 4-(4-Hydroxyphenyl)butan-2-one
Other names Frambinone
Oxyphenylon
Rheosmin
Rasketone
Identifiers
3D model (JSmol)
Abbreviations RK
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Properties
C10H12O2
Molar mass 164.201
Melting point
Boiling point
Hazards
R-phrases R22
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Raspberry ketone is a natural phenolic compound that is the primary aroma compound of red raspberries. It is used in perfumery, in cosmetics, and as a food additive to impart a fruity odor.

In plants, raspberry ketone is synthesized from coumaroyl-CoA.[2] But since the natural abundance of raspberry ketone is very low, it is prepared industrially by a variety of methods from chemical intermediates.[3]

When given to mice in high doses (up to 2% of food intake), raspberry ketone has been shown to prevent high-fat-diet-induced elevations in body weight.[4] This effect is reported to stem from the alteration of lipid metabolism, increasing norepinephrine-induced lipolysis. Although products containing this compound are marketed for weight loss, this effect has not been demonstrated in humans. The Federal Trade Commission recommends against the use of such "miracle diet" products.[5]

References

  1. Catalog of Organics and Fine Chemicals, Acros Organics, 2004/05, page 1250.
  2. MetaCyc Pathway: raspberry ketone biosynthesis
  3. Tateiwa, J.-I., Horiuchi, H., Hashimoto, K., Yamauchi, T., and Uemura, S. 1994. Cation-exchanged montmorillonite-catalyzed facile Friedel-crafts alkylation of hydroxy and methoxy aromatics with 4-hydroxybutan-2-one to produce raspberry ketone and some pharmaceutically active compounds. J. Org. Chem. 59:5901-5904.
  4. Morimoto C, Satoh Y, Hara M, Inoue S, Tsujita T, Okuda H (2005). "Anti-obese action of raspberry ketone". Life Sci. 77 (2): 194–204. doi:10.1016/j.lfs.2004.12.029. PMID 15862604.
  5. Weighing the Evidence in Diet Ads, U.S. Federal Trade Commission

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