Raspberry ketone

Raspberry ketone is a natural phenolic compound that is the primary aroma compound of red raspberries.

Raspberry ketone[1]
Names
IUPAC name
4-(4-Hydroxyphenyl)butan-2-one
Other names
p-Hydroxybenzyl acetone; 4-(p-Hydroxyphenyl)-2-butanone; Frambinone; Oxyphenylon; Rheosmin; Rasketone
Identifiers
3D model (JSmol)
Abbreviations RK
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.024.370
EC Number
  • 226-806-4
UNII
Properties
C10H12O2
Molar mass 164.204 g·mol−1
Appearance White needles[2]
Melting point 82 to 84 °C (180 to 183 °F; 355 to 357 K)
Boiling point 140 to 146 °C (284 to 295 °F; 413 to 419 K) at 0.5 mmHg
Hazards
R-phrases (outdated) R22
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Occurrence

Raspberry ketone occurs in a variety of fruits, including raspberries, cranberries, and blackberries.[3] It is biosynthesized from coumaroyl-CoA.[4] It can be extracted from the fruit, yielding about 1–4 mg per kg of raspberries.[5]

Preparation

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 condensation followed by catalytic hydrogenation. First, acetone is condensed with 4-hydroxybenzaldehyde to form an α,β-unsaturated ketone. Then the alkene part is reduced to the alkane. This two-step method produces raspberry ketone in 99% yield.[7] There is a less expensive hydrogenation catalyst, nickel boride, which also demonstrates high selectivity towards hydrogenation of the double bond of enone.[8]

Uses

Raspberry ketone is sometimes 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.[5] Synthetic raspberry ketone is cheaper, with estimates ranging from a couple of dollars per pound[9] to one fifth of the cost of the natural product.

Marketing

Although products containing this compound are marketed for weight loss, there is no clinical evidence for this effect in humans.[10]

Safety

Little is known about the long-term safety of raspberry ketone supplements,[11][12] especially since little research has been done with humans.[13] Because it is chemically related to the stimulant synephrine, there are some concerns about its safety.[10] Toxicological models indicate a potential for cardiotoxic effects, as well as effects on reproduction and development.[11] Furthermore, in many dietary supplements containing raspberry ketones, manufacturers add other ingredients such as caffeine which may have unsafe effects.[13]

In 1965, the US Food and Drug Administration classified raspberry ketone as generally recognized as safe (GRAS) for the small quantities used to flavor foods.[2]

See also

References
  1. Catalog of Organics and Fine Chemicals, Acros Organics, 2004/05, page 1250.
  2. "4-(p-Hydroxyphenyl)-2-butanone". Food and Cosmetics Toxicology. 16: 781–2. 1978. doi:10.1016/S0015-6264(78)80113-8.
  3. Raspberry Ketone, Molecule of the Month, University of Bristol
  4. "MetaCyc Pathway: raspberry ketone biosynthesis". MetaCyc. Retrieved 2012-07-12.
  5. Beekwilder, Jules; Van Der Meer, Ingrid M.; Sibbesen, Ole; Broekgaarden, Mans; Qvist, Ingmar; Mikkelsen, Joern D.; Hall, Robert D. (2007). "Microbial production of natural raspberry ketone". Biotechnology Journal. 2 (10): 1270–9. doi:10.1002/biot.200700076. PMID 17722151.
  6. Tateiwa, Jun-Ichi; Horiuchi, Hiroki; Hashimoto, Keiji; Yamauchi, Takayoshi; Uemura, Sakae (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". The Journal of Organic Chemistry. 59 (20): 5901–4. doi:10.1021/jo00099a017.
  7. Smith, Leverett 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. S2CID 94729547.
  8. Bandarenko, Mikhail; Kovalenko, Vitaly (2014). "Synthesis of Raspberry and Ginger Ketones by Nickel Boride-catalyzed Hydrogenation of 4-Arylbut-3-en-2-ones". Zeitschrift für Naturforschung B. 69b (8): 885–888. doi:10.5560/ZNB.2014-4118.
  9. "Archived copy". Archived from the original on 2013-03-17. Retrieved 2012-11-06.CS1 maint: archived copy as title (link)
  10. "Raspberry Ketone". WebMD.
  11. Bredsdorff L, Wedebye EB, Nikolov NG, Hallas-Møller T, Pilegaard K (2015). "Raspberry ketone in food supplements - High intake, few toxicity data - A cause for safety concern?". Regul Toxicol Pharmacol. 73 (1): 196–200. doi:10.1016/j.yrtph.2015.06.022. PMID 26160596.
  12. Cathy Wong. "Raspberry Ketones for Weight Loss". About.com.
  13. Canberra, Jules. "What's All The Hype About Raspberry Ketone?". Authority Health. Retrieved 30 October 2017.
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