Raspberry ketone is a natural phenol

Natural phenol

Natural phenols, bioavailable phenols, plant phenolics, low molecular weight phenols or phenoloids are a class of natural products. They are small molecules containing one or more phenolic group. These molecules are smaller in size than polyphenols, containing less than 12 phenolic groups...

ic compound that is the primary aroma compound

Aroma compound

An aroma compound, also known as odorant, aroma, fragrance or flavor, is a chemical compound that has a smell or odor...

 of red raspberries

Raspberry

The raspberry or hindberry is the edible fruit of a multitude of plant species in the genus Rubus, most of which are in the subgenus Idaeobatus; the name also applies to these plants themselves...

. It 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. In 1965, the Food and Drug Administration

Food and Drug Administration

The Food and Drug Administration is an agency of the United States Department of Health and Human Services, one of the United States federal executive departments...

 placed raspberry ketone on generally recognized as safe

Generally recognized as safe

Generally recognized as safe is an American Food and Drug Administration designation that a chemical or substance added to food is considered safe by experts, and so is exempted from the usual Federal Food, Drug, and Cosmetic Act food additive tolerance requirements.-History:On January 1, 1958,...

 (GRAS) status.

In plants, raspberry ketone is synthesized from coumaroyl-CoA

Coumaroyl-CoA

Coumaroyl-Coenzyme A is a chemical compound used in chalcones production, a key compound in the flavonoids and stilbenoids biosynthesis pathways in plants.Raspberry ketone is also synthetized via coumaroyl-coA.-Enzymes using Coumaroyl-Coenzyme A:...

. Extraction of pure raspberry ketone is usually 1-4 mg per kg of raspberries.

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-catalytic hydrogenation. In acetone

Acetone

Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...

 and sodium hydroxide, 4-hydroxybenzaldehyde

4-Hydroxybenzaldehyde

4-Hydroxybenzaldehyde is one of the three isomers of hydroxybenzaldehyde. It can be found in the orchid Gastrodia elata.-Chemistry:The Dakin oxidation is an organic redox reaction in which an ortho- or para-hydroxylated phenyl aldehyde or ketone reacts with hydrogen peroxide in base to form a...

 can form the α,β-unsaturated ketone. This then goes through catalytic hydrogenation to produce raspberry ketone. This method produces a 99% yield.

When given to mice in high doses (up to 2% of food intake), raspberry ketone has been shown to prevent high-fat-diet-induced elevations in body weight. This effect is reported to stem from the alteration of lipid metabolism, increasing norepinephrine

Norepinephrine

Norepinephrine is the US name for noradrenaline , a catecholamine with multiple roles including as a hormone and a neurotransmitter...

-induced lipolysis

Lipolysis

Lipolysis is the breakdown of lipids and involves the hydrolysis of triglycerides into free fatty acids followed by further degradation into acetyl units by beta oxidation. The process produces Ketones, which are found in large quantities in ketosis, a metabolic state that occurs when the liver...

. Although products containing this compound are marketed for weight loss, this effect has not been studied in humans.