Raspberry ketone is a natural phenolic compound that is the primary aroma compound of red raspberries.
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Occurrence
Raspberry ketone occurs in a variety of fruits, including raspberries, cranberries, and blackberries. It is biosynthesized from coumaroyl-CoA. It can be extracted from the fruit, yielding about 1-4 mg per kg of raspberries.
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Preparation
Since the natural abundance of raspberry ketone is very low, it is prepared industrially by a variety of methods from chemical intermediates. 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 ?,?-unsaturated ketone. Then the alkene portion is reduced to the alkane. This two-step method produces raspberry ketone in 99% yield.
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. Synthetic raspberry ketone is cheaper, with estimates ranging from a couple of dollars per pound to one fifth of the cost of the natural product.
Putative health effects
Although products containing this compound are marketed for weight loss, there is no clinical evidence for this effect in humans. The average daily intake of dietary raspberry ketone has been estimated as 0.42 mg/kg/day. 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. 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. 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.
Safety
Little is known about the long-term safety of raspberry ketone supplements. Because it is chemically related to the stimulant synephrine, there are some concerns about its safety. Toxicological models indicate a potential for cardiotoxic effects, as well as effects on reproduction and development.
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. In the UK, raspberry ketone supplements are on the Food Standards Agency's unauthorized list.
Source of the article : Wikipedia
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