![]() | |
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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)
|
|
Abbreviations | RK |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.024.370 |
EC Number |
|
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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: | |
![]() | |
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).
|
Raspberry ketone is a natural phenolic compound that is the primary aroma compound of red raspberries.
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]
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]
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]
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.
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]
![]() | |
![]() | |
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 |
EC Number |
|
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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: | |
![]() | |
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).
|
Raspberry ketone is a natural phenolic compound that is the primary aroma compound of red raspberries.
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]
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]
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]
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.
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]