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Merck

00390580

Rosmarinic acid

primary reference standard

Sinónimos:

(R)-O-(3,4-Dihydroxycinnamoyl)-3-(3,4- dihydroxyphenyl)lactic acid, 3,4-Dihydroxycinnamic acid (R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethyl ester

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About This Item

Fórmula empírica (notación de Hill):
C18H16O8
Número de CAS:
Peso molecular:
360.31
Beilstein/REAXYS Number:
2227587
MDL number:
UNSPSC Code:
85151701
PubChem Substance ID:
NACRES:
NA.24

grade

primary reference standard

shelf life

limited shelf life, expiry date on the label

manufacturer/tradename

HWI

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

171-175 °C (lit.)

storage temp.

−20°C

SMILES string

OC(=O)[C@@H](Cc1ccc(O)c(O)c1)OC(=O)\C=C\c2ccc(O)c(O)c2

InChI

1S/C18H16O8/c19-12-4-1-10(7-14(12)21)3-6-17(23)26-16(18(24)25)9-11-2-5-13(20)15(22)8-11/h1-8,16,19-22H,9H2,(H,24,25)/b6-3+/t16-/m1/s1

InChI key

DOUMFZQKYFQNTF-WUTVXBCWSA-N

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General description

Produced and qualified by HWI pharma services GmbH.
Exact content by quantitative NMR can be found on the certificate.

Application

Reference standard in the analysis of herbal medicinal products.

Biochem/physiol Actions

Rosmarinic acid has shown to contain antioxidant and anti-inflammatory activities. Possesses promising physiological actions related to cognitive performance, Alzheimer′s disease prevention, kidney disease treatment, cardioprotection and cancer chemoprevention.

Other Notes

This compound is commonly found in plants of the genus: melissa mentha salvia thymus

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Critical reviews in biotechnology, 32(3), 203-217 (2011-08-16)
Rosmarinic acid (RA) is one of the first secondary metabolites produced in plant cell cultures in extremely high yields, up to 19% of the cell dry weight. More complex derivatives of RA, such as rabdosiin and lithospermic acid B, later
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Journal of cellular physiology, 228(5), 975-982 (2012-10-09)
High mobility group box 1 (HMGB1) protein is a crucial cytokine that mediates response to infection, injury, and inflammation. Rosmarinic acid (RA) is an important component of the leaves of Perilla frutescens and has neuroprotective, anti-microbial, anti-oxidant, and anti-cancer effects
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Efforts to introduce pathogen resistance into landscape tree species by breeding may have unintended consequences for fungal diversity. To address this issue, we compared the frequency and diversity of endophytic fungi and defensive phenolic metabolites in elm (Ulmus spp.) trees

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