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Rosmarinic acid

Rosmarinic acid
Rosmarinic acid
Names
IUPAC name
(2R)-2-[[(2''E'')-3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]]oxy]-3-(3,4-dihydroxyphenyl)propanoic acid
Identifiers
20283-92-5 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:17226 YesY
ChEMBL ChEMBL324842 N
ChemSpider 4474888 YesY
ECHA InfoCard 100.123.507
PubChem 5315615
Properties
C18H16O8
Molar mass 360.32 g·mol−1
Appearance Red-orange powder
Melting point 171 to 175 °C (340 to 347 °F; 444 to 448 K)
Slightly soluble
Solubility in other solvents Well soluble in most organic solvents
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Rosmarinic acid is a chemical compound found in a variety of plants. It has antioxidant properties.

Rosmarinic acid was first isolated and characterized in 1958 by the Italian chemists M. L. Scarpatti and G. Oriente from rosemary (Rosmarinus officinalis).

Chemically, rosmarinic acid is a caffeic acid ester of salvianic acid A (3,4-dihydroxyphenyllactic acid).

Rosmarinic acid accumulation is shown in hornworts, in the fern family Blechnaceae and in species of several orders of mono- and dicotyledonous angiosperms.

It is found most notably in many Lamiaceae (dicotyledons in the order Lamiales), especially in the subfamily Nepetoideae. It is found in species used commonly as culinary herbs such as Ocimum basilicum (basil), Ocimum tenuiflorum (holy basil), Melissa officinalis (lemon balm), Rosmarinus officinalis (rosemary), Origanum majorana (marjoram), Salvia officinalis (sage), thyme and peppermint or in plants with medicinal properties such as common self-heal (Prunella vulgaris) or species in the genus Stachys.

It is also found in other Lamiales such as Heliotropium foertherianum, a plant in the family Boraginaceae.

It is also found in plants in the family Marantaceae (monocotyledons in the order Zingiberales) such as species in the genera Maranta (Maranta leuconeura, Maranta depressa) and Thalia (Thalia geniculata).


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