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Raspberry ketone



Raspberry ketone[1]
IUPAC name 4-(4-Hydroxyphenyl)butan-2-one
Other names Frambinone
Oxyphenalon
Rheosmin
Rasketone
Identifiers
Abbreviations RK
CAS number 5471-51-2
PubChem 21648
EINECS number 226-806-4
SMILES CC(=O)CCC1=CC=C(C=C1)O
Properties
Molecular formula C10H12O2
Molar mass 164.201
Melting point

82-84 °C

Boiling point

140-146 °C (at 0.5 mmHg)

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.

Additional recommended knowledge

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.

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.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Raspberry_ketone". A list of authors is available in Wikipedia.
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