Raspberry ketone

Raspberry ketone[1]

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

CAS Number

* 5471-51-2 Y

3D model (JSmol)

* Interactive image

Abbreviations  | RK
ChEBI |

* CHEBI:68656 Y

ChEMBL |

* ChEMBL105912 Y

ChemSpider |

* 20347 Y

ECHA InfoCard | 100.024.370
EC Number |

* 226-806-4

PubChem CID

* 21648

UNII |

* 7QY1MH15BG Y

CompTox Dashboard (EPA)

* DTXSID5044495

InChI

* InChI=1S/C10H12O2/c1-8(11)2-3-9-4-6-10(12)7-5-9/h4-7,12H,2-3H2,1H3 Y

Key: NJGBTKGETPDVIK-UHFFFAOYSA-N Y

* 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

SMILES

* O=C(CCc1ccc(O)cc1)C

Properties

Chemical formula

| 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:

Pictograms

Signal word

| Warning

Hazard statements

| H302

Precautionary statements

| 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 YN ?)

Infobox references

Chemical compound

Raspberry ketone is a naturally occurring 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. anosmum),[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 Claisen-Schmidt 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]

## 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]

## Marketing

[edit]

Although products containing this compound are marketed for weight loss, there is no clinical evidence for this effect in humans.[13][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] 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]

* Raspberry ellagitannin

## 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.; 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.; 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.; 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:10.26786/1920-7603(2018)19.
7. ^ Nakahira, M.; Ono, H.; Wee, S.L.; Nishida, R. (2018). "Floral synomone diversification of Bulbophyllum sibling species (Orchidaceae) in attracting fruit fly pollinators". Biochemical Systematics and Ecology. 81: 86–95. doi:10.1016/j.bse.2018.10.002. hdl:2433/235528.
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. S2CID 32088996.
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. ^ "Raspberry Ketones: Uses, Health Benefits, and Risks". WebMD.
14. ^ "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. S2CID 38312188.
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.

Authority control databases: National |

* Germany

|

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[H302]: H302: Harmful if swallowed
*[P264]: P264: Wash ... thoroughly after handling.
*[P270]: P270: Do not eat, drink or smoke when using this product.
*[P301+P312]: P301+P312: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.
*[P330]: P330: Rinse mouth.
*[P501]: P501: Dispose of contents/container to ...