Carnosic acid

Structural formula
General
Surname	Carnosic acid
other names	Salvin; (4a R , 10a S ) -5,6-Dihydroxy-1,1-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydro-phenanthrene-4a-carboxylic acid ( IUPAC ) ;
Molecular formula	C 20 H 28 O 4
Brief description	yellow powder with a bitter taste
External identifiers / databases
EC number	609-253-7
ECHA InfoCard	100.110.784
PubChem	65126
ChemSpider	58635
Wikidata	Q412827
properties
Molar mass	332.43 g mol −1
Physical state	firmly
Melting point	185–190 ° C (decomposition)
solubility	easily soluble in lipids , hexane , diethyl ether ; almost insoluble in water;
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

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

history

Carnic acid was first discovered in 1962 by Horst Linde in Salvia officinalis . In 1969 Carl Heinz Brieskorn recognized that carnosic acid and carnosol (picrosalvin) cause the special antioxidant effect of rosemary and sage and that carnosic acid has the greatest antioxidant activity.

properties

Ferruginol, the parent compound of the tricyclic phenols from rosemary and sage

Carnosic acid is a bitter-tasting, yellow powder and can be isolated from the plants by solvent extraction using hexane and / or ethanol or high-pressure extraction using supercritical carbon dioxide . Oxygen in the air oxidizes carnosic acid to the unstable hydroxycarnosic acid , which is converted into carnosol, a lactone . In addition to its antioxidant properties, carnosic acid also has antimicrobial properties , for example against Staphylococcus aureus . This is attributed to an inhibition of nucleic acid biosynthesis in bacteria. In animal experiments, carnosic acid also showed chemoprotective effects 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 and in animal feed. In an opinion from June 2008, the European Food Safety Authority (EFSA) certified the harmlessness of carnosic acid for use in food. In the USA , rosemary oil, which contains up to 30% carnosic acid and carnosol, has been classified as Generally Recognized As Safe (GRAS) since 1965 (FEMA) and 1970 ( FDA ) and can be used in food.

proof

The antioxidant phenols from Salvia species can be quantitatively determined using high-performance liquid chromatography ( HPLC ) with butylhydroxyanisole ( BHA ) as the standard.

Web links

Use of rosemary extracts as food additives (EFSA)
Trace analysis of carnosic acid, p-cymene-2,3-diol, thymol, piperine and the piperine isomers in matrices of animal origin. DNB 957133359/34

Individual evidence

↑ ^a ^b ^c Data sheet Carnosic acid from Rosmarinus officinalis from Sigma-Aldrich , accessed on December 23, 2019 ( PDF ).
↑ ^a ^b ^c ^d R. Hansel, K. Keller, H. Rimpler, G. Schneider (eds.): Hager's handbook of pharmaceutical practice. Volume 6, Drugs P-Z , 5th Edition, Springer, 1994, ISBN 3-540-52639-0 , pp. 496-500, 551-557.
↑ ^a ^b ^c Shmuel Yannai: Dictionary of food compounds with CD-ROM: additives, flavors, and ingredients. Volume 3, G – L, Chapman & Hall / CRC Press, 2004, ISBN 978-1-58488-416-3 , p. 13.
^ Gerhard G. Habermehl, Peter E. Hammann, Hans C. Krebs, W. Ternes: Naturstoffchemie: An introduction. 3rd edition, Springer, 2008, ISBN 978-3-540-73732-2 , p. 26.
↑ US Patent 6231896: Chewing gum base stabilized with carnosic acid May 15, 2001, Goodyear Tire & Rubber Company.
↑ Horst Linde: A new diterpene from Salvia officinalis L. and a note on the constitution of picrosalvin. In: Helvetica Chimica Acta. 47, 1964, pp. 1234-1239, doi : 10.1002 / hlca.19640470517 .
↑ ^a ^b astro-verl.com: Carnosic acid
^ M. Danilenko, X. Wang, GP Studzinksi: Carnosic Acid and Promotion of Monocytic Differentiation of HL60-G Cells Initiated by Other Agents. In: JNCI Journal of the National Cancer Institute. 93, 2001, pp. 1224-1233, doi : 10.1093 / jnci / 93.16.1224 .
↑ ^a ^b EFSA: Use of rosemary extracts as a food additive - Scientific Opinion of the Panel on Food Additives, Flavors, Processing Aids and Materials in Contact with Food. In: EFSA Journal. 6, 2008, p. 721, doi : 10.2903 / j.efsa.2008.721 .
↑ EFSA: Use of rosemary extracts as food additives - Scientific opinion of the Panel on Food Additives, Flavorings, Processing Aids and Materials in Contact with Food. ( Memento of September 13, 2009 in the Internet Archive ) June 12, 2008.

[sigma-1] Data sheet Carnosic acid from Rosmarinus officinalis from Sigma-Aldrich , accessed on December 23, 2019 ( PDF ).

[hager-2] R. Hansel, K. Keller, H. Rimpler, G. Schneider (eds.): Hager's handbook of pharmaceutical practice. Volume 6, Drugs P-Z , 5th Edition, Springer, 1994, ISBN 3-540-52639-0 , pp. 496-500, 551-557.

[Shmuel-3] Shmuel Yannai: Dictionary of food compounds with CD-ROM: additives, flavors, and ingredients. Volume 3, G – L, Chapman & Hall / CRC Press, 2004, ISBN 978-1-58488-416-3 , p. 13.

[4] Gerhard G. Habermehl, Peter E. Hammann, Hans C. Krebs, W. Ternes: Naturstoffchemie: An introduction. 3rd edition, Springer, 2008, ISBN 978-3-540-73732-2 , p. 26.

[5] US Patent 6231896: Chewing gum base stabilized with carnosic acid May 15, 2001, Goodyear Tire & Rubber Company.

[6] Horst Linde: A new diterpene from Salvia officinalis L. and a note on the constitution of picrosalvin. In: Helvetica Chimica Acta. 47, 1964, pp. 1234-1239, doi : 10.1002 / hlca.19640470517 .

[astro-7] stro-verl.com: Carnosic acid

[8] M. Danilenko, X. Wang, GP Studzinksi: Carnosic Acid and Promotion of Monocytic Differentiation of HL60-G Cells Initiated by Other Agents. In: JNCI Journal of the National Cancer Institute. 93, 2001, pp. 1224-1233, doi : 10.1093 / jnci / 93.16.1224 .

[efsa1-9] EFSA: Use of rosemary extracts as a food additive - Scientific Opinion of the Panel on Food Additives, Flavors, Processing Aids and Materials in Contact with Food. In: EFSA Journal. 6, 2008, p. 721, doi : 10.2903 / j.efsa.2008.721 .

[10] EFSA: Use of rosemary extracts as food additives - Scientific opinion of the Panel on Food Additives, Flavorings, Processing Aids and Materials in Contact with Food. ( Memento of September 13, 2009 in the Internet Archive ) June 12, 2008.