Raspberry ketone
Chemical compound From Wikipedia, the free encyclopedia
Raspberry ketone is a naturally occurring phenolic compound that is the primary aroma compound of red raspberries.
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| 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) |
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| Abbreviations | RK |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.024.370 |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| 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: | |
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| 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).
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Occurrence
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
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
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
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
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
References
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