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Carnosic acid

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Carnosic acid
Chemical structure of carnosic acid
Names
IUPAC name 11,12-Dihydroxyabieta-8,11,13-trien-20-oic acid
Systematic IUPAC name (4aR,10aS)-5,6-Dihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,3,4,9,10,10a-hexahydrophenanthrene-4a(2H)-carboxylic acid
Other names Salvin
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.110.784 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C20H28O4/c1-11(2)13-10-12-6-7-14-19(3,4)8-5-9-20(14,18(23)24)15(12)17(22)16(13)21/h10-11,14,21-22H,5-9H2,1-4H3,(H,23,24)/t14-,20+/m0/s1Key: QRYRORQUOLYVBU-VBKZILBWSA-N
  • InChI=1/C20H28O4/c1-11(2)13-10-12-6-7-14-19(3,4)8-5-9-20(14,18(23)24)15(12)17(22)16(13)21/h10-11,14,21-22H,5-9H2,1-4H3,(H,23,24)/t14-,20+/m0/s1Key: QRYRORQUOLYVBU-VBKZILBWBB
SMILES
  • CC(C)C1=C(C(=C2C(=C1)CCC3C2(CCCC3(C)C)C(=O)O)O)O
Properties
Chemical formula C20H28O4
Molar mass 332.440 g·mol
Melting point 185 to 190 °C (365 to 374 °F; 458 to 463 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Carnosic acid is a natural benzenediol abietane diterpene found in rosemary (Rosmarinus officinalis) and common sage (Salvia officinalis). Dried leaves of rosemary and sage contain 1.5 to 2.5% carnosic acid.

Carnosic acid and carnosol, a derivative of the acid, are used as antioxidant preservatives in food and nonfood products, where they're labelled as "extracts of rosemary" (E392).

References

  1. Schwarz, Karin; Ternes, Waldemar (1992). "Antioxidative constituents of Rosmarinus officinalis and Salvia officinalis". Zeitschrift für Lebensmittel-Untersuchung und -Forschung. 195 (2): 99–103. doi:10.1007/BF01201766. PMID 1529648. S2CID 100385294.
  2. Birtić, Simona; Dussort, Pierre; Pierre, François-Xavier; Bily, Antoine C.; Roller, Marc (2015-07-01). "Carnosic acid". Phytochemistry. 115: 9–19. Bibcode:2015PChem.115....9B. doi:10.1016/j.phytochem.2014.12.026. ISSN 0031-9422. PMID 25639596.
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