Raspberry ketone

Raspberry ketone
Raspberry ketone[1]
Abbreviations RK
CAS number 5471-51-2
PubChem 21648
ChemSpider 20347 YesY
EC number 226-806-4
Jmol-3D images Image 1
Molecular formula C10H12O2
Molar mass 164.2 g mol−1
Appearance White needles[2]
Melting point

82-84 °C

Boiling point

140-146 °C (at 0.5 mmHg)

R-phrases R22
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox 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. It is one of the most expensive natural flavor components used in the food industry. The natural compound can cost as much as $20,000 per kg.[3] In 1965, the Food and Drug Administration placed raspberry ketone on generally recognized as safe (GRAS) status.[4]

In plants, raspberry ketone is synthesized from coumaroyl-CoA.[5] Extraction of pure raspberry ketone is usually 1-4 mg per kg of raspberries.[3]

Since the natural abundance of raspberry ketone is very low, it is prepared industrially by a variety of methods from chemical intermediates.[6] One of the ways this can be done is through a crossed aldol-catalytic hydrogenation. In acetone and sodium hydroxide, 4-hydroxybenzaldehyde can form the α,β-unsaturated ketone. This then goes through catalytic hydrogenation to produce raspberry ketone. This method produces a 99% yield.[7]

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.[8] 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 studied in humans.


  1. ^ Catalog of Organics and Fine Chemicals, Acros Organics, 2004/05, page 1250.
  2. ^ Opdyke, D. L. J. (1978). "4-(p-Hydroxyphenyl)-2-butanone". Fd. Cosmet. Toxicol. 16: 781–782. doi:10.1016/S0015-6264(78)80113-8. 
  3. ^ a b Beekwilder, J.; Van der Meer, I.; Sibbesen, O.; Broekgaarden, M.; Qvist, I.; Mikkelsen, J.; Hall, R. (2007). "Microbial production of natural raspberry ketone". Biotechnol. J. 2 (10): 1270–1279. doi:10.1002/biot.200700076. PMID 17722151. 
  4. ^ Opdyke, D. L. J. 4-(p-Hydroxyphenyl)-2-butanone. Fd. Cosmet. Toxicol. 1978, 16, 781-782.
  5. ^ MetaCyc Pathway: raspberry ketone biosynthesis
  6. ^ 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 (20): 5901–5904. doi:10.1021/jo00099a017. 
  7. ^ Smith, L. R. (1996). "Rheosmin (“Raspberry Ketone”) and Zingerone, and Their Preparation by Crossed Aldol-Catalytic Hydrogenation Sequences". The Chemical Educator 1 (3): 1–18. doi:10.1007/s00897960034a. 
  8. ^ 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. 

Wikimedia Foundation. 2010.

Игры ⚽ Поможем сделать НИР

Look at other dictionaries:

  • Raspberry — This article is about the various species of raspberry in the plant genus Rubus. For the widely cultivated Eurasian red raspberry, see Rubus idaeus. For the North American black raspberry, see Rubus occidentalis. For other uses, see Raspberry… …   Wikipedia

  • Nidula — candida Scientific classification Kingdom: Fungi Division …   Wikipedia

  • Coumaroyl-CoA — Coumaroyl Coenzyme A IUPAC name S [2 [3 [[4 [[[(2R,3S,4R,5R) 5 (6 aminopurin 9 yl) 4 hydroxy 3 phosphonooxyoxolan 2 yl]methoxy hydroxyphosph …   Wikipedia

  • 4-(4-Hydroxyphenyl)butan-2-on — Strukturformel Allgemeines Name 4 (4 Hydroxyphenyl) butan 2 on Andere Namen Rheosmin …   Deutsch Wikipedia

  • Oxyphenylon — Strukturformel Allgemeines Name 4 (4 Hydroxyphenyl) butan 2 on Andere Namen Rheosmin Himbeerketon …   Deutsch Wikipedia

  • Rheosmin — Strukturformel Allgemeines Name 4 (4 Hydroxyphenyl) butan 2 on Andere Namen Rheosmin Himbeerketon …   Deutsch Wikipedia

  • Himbeerketon — Strukturformel Allgemeines Name 4 (4 Hydroxyphenyl) butan 2 on Andere …   Deutsch Wikipedia

  • Phenols — In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of a hydroxyl group ( OH) bonded directly to an aromatic hydrocarbon group. The simplest of the class is phenol also called as carbolic acid… …   Wikipedia

  • Aroma of wine — It is through smelling a wine that most of the flavor notes associated with wine are detected. It is through the aromas of wine that wine is actually tasted. The human tongue is limited to the primary tastes perceived by taste receptors on the… …   Wikipedia

  • Pollinator — A pollinator is the biotic agent (vector) that moves pollen from the male anthers of a flower to the female stigma of a flower to accomplish fertilization or syngamy of the female gamete in the ovule of the flower by the male gamete from the… …   Wikipedia

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”