Carnosic acid

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Carnosic acid
Chemical structure of carnosic acid
Names
IUPAC name
(4aR,10aS)-5,6-Dihydroxy-1,1-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid
Other names
Salvin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.110.784 Edit this at Wikidata
UNII
  • 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/s1 ☒N
    Key: QRYRORQUOLYVBU-VBKZILBWSA-N ☒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/s1
    Key: QRYRORQUOLYVBU-VBKZILBWBB
  • CC(C)C1=C(C(=C2C(=C1)CCC3C2(CCCC3(C)C)C(=O)O)O)O
Properties
C20H28O4
Molar mass 332.440 g·mol−1
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 [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Carnosic acid is a natural benzenediol abietane diterpene found in rosemary (Rosmarinus officinalis) and common sage (Salvia officinalis).[1] Dried leaves of rosemary or sage contain 1.5 to 2.5% carnosic acid.

Carnosic acid is used as a preservative or antioxidant in food and nonfood products (e.g. toothpaste, mouthwash and chewing gum -in which it has an antimicrobial effect on the microbes responsible for bad breath- or skin care products).[citation needed]

References

  1. ^ Schwarz, Karin; Ternes, Waldemar (1992). "Antioxidative constituents of Rosmarinus officinalis and Salvia officinalis". Zeitschrift für Lebensmittel-Untersuchung und -Forschung. 195: 99–103. doi:10.1007/BF01201766.

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