Carnosic acid

• Salvin
• ( 4aR, 10aS ) -5,6 -dihydroxy-1 ,1 -dimethyl -7 -propan- 2-yl -2, 3,4,9,10,10 a- hexahydro- phenanthren -4a -carboxylic acid ( IUPAC)

Yellow powder with a bitter taste

Fixed

185-190 ° C ( decomposition)

• Readily soluble in lipids, hexane, diethyl ether
• Almost insoluble in water

Template: Infobox chemical / molecular formula search available

Carnosic acid is a chemical compound that occurs in nature in sage (Salvia ) and rosemary species. The carboxylic acid from the group of derivatives is one of the ferruginol phenols and diterpenes. Dried sage or rosemary leaves contain between 1.5 and 2.5 % carnosic acid.

History

The Carnolsäure was first discovered in 1962 by Horst Linde in Salvia officinalis. 1969 saw Carl Heinz Brieskorn that carnosic acid and carnosol ( Pikrosalvin ) require the special antioxidant effect of rosemary and sage and carnosic acid shows the greatest antioxidant activity.

Properties

Carnosic acid is a bitter-tasting, yellow powder and can be isolated by means of carbon dioxide from the plants by solvent extraction using hexane and / or ethanol or supercritical fluid extraction. By atmospheric oxygen carnosic acid is oxidized to unstable Hydroxycarnosolsäure that for carnosol, a lactone reacts. In addition to the antioxidant carnosic acid also possesses antimicrobial activity, such as Staphylococcus aureus. This is attributed to inhibition of Nucleinsäurebiosynthese in bacteria. In animal experiments, carnosic acid also showed chemoprotective effect against carcinogens.

Use

Carnosic acid is used as a fat-soluble antioxidant, preservative and flavoring agent in foods such as meat products, oils and fats, flour, milk powder, fish products, sauces, as well as in animal feed. In a report dated June 2008, the European Food Safety Authority (EFSA ) certified the safety of carnosic acid for use in foods. In the U.S. owns rosemary oil, which contains up to 30 % carnosic acid and carnosol, since 1965 ( FEMA) and 1970 (FDA ) classification as GRAS (Generally Reported as safe) and can be used in food.

Proof

The antioxidant phenolics from Salvia species can be determined as a standard quantitative high performance liquid chromatography (HPLC) with butylated hydroxyanisole ( BHA).