Raspberry ketone

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Raspberry ketone[1]
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Names
IUPAC name
4-(4-Hydroxyphenyl)butan-2-one
Other names
p-Hydroxybenzyl acetone; 4-(p-Hydroxyphenyl)-2-butanone; Frambinone; Oxyphenylon; Rheosmin; Rasketone
Identifiers
5471-51-2 N
Abbreviations RK
ChEBI CHEBI:68656 N
ChEMBL ChEMBL105912 YesY
ChemSpider 20347 YesY
EC Number 226-806-4
Jmol 3D model Interactive image
PubChem 21648
UNII 7QY1MH15BG N
  • InChI=1S/C10H12O2/c1-8(11)2-3-9-4-6-10(12)7-5-9/h4-7,12H,2-3H2,1H3 YesY
    Key: NJGBTKGETPDVIK-UHFFFAOYSA-N YesY
  • 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 164.20 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
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

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

Occurrence

Raspberry ketone occurs in a variety of fruits including raspberries, cranberries and blackberries.[3] It is biosynthesized from coumaroyl-CoA.[4] Extraction of pure raspberry ketone is usually 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-catalytic hydrogenation. In acetone and sodium hydroxide, 4-hydroxybenzaldehyde can form the α,β-unsaturated ketone. This then goes through catalytic hydrogenation to produce raspberry ketone. This method produces a 99% yield.[7]

Uses

Raspberry ketone is 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[8] to one fifth of the cost of natural product.[9]

Putative health effects

Although products containing this compound are marketed for weight loss, there is no clinical evidence for this effect in humans.[10] The average daily intake of dietary raspberry ketone has been estimated as 0.42 mg/kg/day.[11] Early studies in rats looking into the potential toxicity of raspberry ketone found no effects on the body weight of rats with doses up to 100 mg/kg, 238 times greater than the estimated intake for humans or 0.01% of body weight.[11] A more recent study demonstrated that when mice were fed very high doses of raspberry ketone, 2% of their diet by weight, there was a statistically significant prevention of high-fat-diet-induced elevation in body weight.[12] The high dose effect is reported to stem from the alteration of lipid metabolism, increasing norepinephrine-induced lipolysis and fatty acid oxidation in cultured adipocytes.[13]

Nutritional supplement manufacturer Andrew Lessman criticized and countered sensationalized media and marketing claims about raspberry ketone’s purported weight-loss benefits and strongly cautioned against its use.[14]

Safety

Little is known about the long term safety of raspberry ketone supplements.[15][16] 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.[15]

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] In the UK, raspberry ketone supplements are on the Food Standards Agency's unauthorized list.[17]

References

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  1. ↑ Catalog of Organics and Fine Chemicals, Acros Organics, 2004/05, page 1250.
  2. ↑ 2.0 2.1 Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Raspberry Ketone, Molecule of the Month, University of Bristol
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ 5.0 5.1 Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ http://www.wordsonwellness.com/post/2012/06/13/With-All-Due-Respect-to-Dr-Oz-Raspberry-Ketone-is-not-a-Fat-Burning-Miracle.aspx
  9. ↑ Why no Raspberry Ketones at NOW Foods?, The Herbal Insider, accessed 2013-03-15
  10. ↑ 10.0 10.1 Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ 11.0 11.1 Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ 15.0 15.1 Lua error in package.lua at line 80: module 'strict' not found.
  16. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  17. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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