Raspberry ketone

From Wikipedia, the free encyclopedia
Raspberry ketone[1]
Structural formula of raspberry ketone
Ball-and-stick model of raspberry ketone
Names
Preferred 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 Edit this at Wikidata
EC Number
  • 226-806-4
UNII
  • InChI=1S/C10H12O2/c1-8(11)2-3-9-4-6-10(12)7-5-9/h4-7,12H,2-3H2,1H3 checkY
    Key: NJGBTKGETPDVIK-UHFFFAOYSA-N checkY
  • InChI=1/C10H12O2/c1-8(11)2-3-9-4-6-10(12)7-5-9/h4-7,12H,2-3H2,1H3
    Key: NJGBTKGETPDVIK-UHFFFAOYAT
  • O=C(CCc1ccc(O)cc1)C
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
GHS labelling:
GHS07: Exclamation mark
Warning
H302
P264, P270, P301+P312, P330, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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

Occurrence[edit]

Raspberry ketone occurs in a variety of fruits, including raspberries, cranberries, and blackberries.[3] It is detected and released by orchid flowers, e.g. Dendrobium superbum (syn D. annosmum),[4] and several Bulbophyllum species [5] [6] [7] to attract raspberry ketone-responsive male Dacini fruit flies. It is biosynthesized from coumaroyl-CoA.[8] It can be extracted from the fruit, yielding about 1–4 mg per kg of raspberries.[9]

Preparation[edit]

Since the natural abundance of raspberry ketone is very low, it is prepared industrially by a variety of methods from chemical intermediates.[10] 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.[11] There is a less expensive hydrogenation catalyst, nickel boride, which also demonstrates high selectivity towards hydrogenation of the double bond of enone.[12]

Raspberry ketone synthesis.png

Uses[edit]

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.[9] Synthetic raspberry ketone is cheaper, with estimates ranging from a couple of dollars per pound[13] to one fifth of the cost of the natural product.[citation needed]

Marketing[edit]

Although products containing this compound are marketed for weight loss, there is no clinical evidence for this effect in humans.[14] They are called "ketones", because of the ketone (acetone) group at their end, which is shared with ketone bodies.

Safety[edit]

Little is known about the long-term safety of raspberry ketone supplements,[15][16] especially since little research has been done with humans.[17] Because it is chemically related to the stimulant synephrine, there are some concerns about its safety.[14] Toxicological models indicate a potential for cardiotoxic effects, as well as effects on reproduction and development.[15] Furthermore, in many dietary supplements containing raspberry ketones, manufacturers add other ingredients such as caffeine which may have unsafe effects.[17]

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[edit]

References[edit]

  1. ^ Catalog of Organics and Fine Chemicals, Acros Organics, 2004/05, page 1250.
  2. ^ a b "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. ^ Nishida, R., Iwahashi, I. and Tan, K.H. 1993. Accumulation of Dendrobium (Orchidaceae) flower fragrance in the rectal glands by males of the melon fly, Dacus cucurbitae (Tephritidae). Journal of Chemical Ecology 19: 713-722. doi:10.1007/BF00985003
  5. ^ Tan, K.H. and Nishida, R. 2005. Synomone or Kairomone? - Bulbophyllum apertum (Orchidaceae) flower releases raspberry ketone to attract Bactrocera fruit flies. Journal of Chemical Ecology. 31(3): 509-519. doi:10.1007/s10886-005-2023-8
  6. ^ Tan, K.H. and Tan, L.T. 2018. Movements of floral parts and roles of the tooth on column wall of Bulbophyllum praetervisum (Orchidaceae) flower for pollination by Dacini fruit flies (Diptera: Tephritidae). Journal of Pollination Ecology 24(17): 157-163. doi.org/10.26786/1920-7603(2018)19
  7. ^ Nakahira, M., Ono, H., Wee, S.L., Tan, K.H. and Nishida, R. 2018. Floral synomone diversification of Bulbophyllum sibling species (Orchidaceae) in attracting fruit fly pollinators. Biochemical Systematics and Ecology, 81: 86-95. doi.org/10.1016/j.bse.2018.10.002
  8. ^ "MetaCyc Pathway: raspberry ketone biosynthesis". MetaCyc. Retrieved 2012-07-12.
  9. ^ a b 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.
  10. ^ 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.
  11. ^ 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.
  12. ^ 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.
  13. ^ "Andrew Lessman's Blog | with All Due Respect to Dr. Oz: Raspberry Ketone is not a Fat-Burning Miracle". Archived from the original on 2013-03-17. Retrieved 2012-11-06.
  14. ^ a b "Raspberry Ketone". WebMD.
  15. ^ a b 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.
  16. ^ Cathy Wong. "Raspberry Ketones for Weight Loss". About.com.
  17. ^ a b Canberra, Jules. "What's All The Hype About Raspberry Ketone?". Authority Health. Retrieved 30 October 2017.