Carnosic acid

Last updated
Carnosic acid
Carnosic acid.svg
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.110.784 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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 X mark.svgN
    Key: QRYRORQUOLYVBU-VBKZILBWSA-N X mark.svgN
  • 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).
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Carnosic acid is a natural benzenediol abietane diterpene found in rosemary ( Rosmarinus officinalis ) and common sage ( Salvia officinalis ). [1] 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). [2]

Related Research Articles

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Salvia rosmarinus, commonly known as rosemary, is a shrub with fragrant, evergreen, needle-like leaves and white, pink, purple, or blue flowers, native to the Mediterranean region. Until 2017, it was known by the scientific name Rosmarinus officinalis, now a synonym.

<span class="mw-page-title-main">Thujone</span> Group of four possible stereoisomers found in various plants: a.o., absinthe and mint

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<span class="mw-page-title-main">Rosmarinus</span> Clade of herbs

Rosmarinus is a small taxonomic clade of woody, perennial herbs with fragrant evergreen needle-like leaves in the family Lamiaceae, native to the Mediterranean Basin.

<i>Salvia officinalis</i> Species of plant

Salvia officinalis, the common sage or just sage, is a perennial, evergreen subshrub, with woody stems, grayish leaves, and blue to purplish flowers. It is a member of the mint family Lamiaceae and native to the Mediterranean region, though it has been naturalized in many places throughout the world. It has a long history of medicinal and culinary use, and in modern times it has been used as an ornamental garden plant. The common name "sage" is also used for closely related species and cultivars.

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Salvia elegans, a species with several varieties including pineapple sage and tangerine sage, is a perennial shrub native to Mexico. It inhabits Madrean and Mesoamerican pine-oak forests between 6,000 and 9,000 ft.

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<i>Officinalis</i>

Officinalis, or officinale, is a Medieval Latin epithet denoting organisms—mainly plants—with uses in medicine, herbalism and cookery. It commonly occurs as a specific epithet, the second term of a two-part botanical name. Officinalis is used to modify masculine and feminine nouns, while officinale is used for neuter nouns.

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Taxodone is a naturally occurring diterpenoid found in Taxodium distichum, Rosmarinus officinalis (rosemary), several salvia species and other plants, along with its oxidized rearrangement product, taxodione. Taxodone and taxodione exhibit anticancer, antibacterial, antioxidant, antifungal, insecticide, and antifeedant activities.

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(+)-camphene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-camphene-forming]. This enzyme catalyses the following chemical reaction

(+)-α-pinene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-α-pinene-forming]. This enzyme catalyses the following chemical reaction

(+)-β-Pinene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [(+)-β-pinene-forming]. This enzyme catalyses the following chemical reaction

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.