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00390580

Rosmarinic acid

primary reference standard

Synonym(s):

(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

Empirical Formula (Hill Notation):
C18H16O8
CAS Number:
20283-92-5
Molecular Weight:
360.31
Beilstein:
2227587
MDL number:
MFCD00017740
UNSPSC Code:
85151701
PubChem Substance ID:
329747058
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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
HWI02735-1
HWI02133-1
HWI00981
HWI00131-4
HWI00131-3

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Rodrigo Lucarini et al.
Pharmaceutical biology, 51(9), 1087-1090 (2013-06-07)
Despite several pharmacological applications of Rosmarinus officinalis L. (Lamiaceae), studies on its analgesic and anti-inflammatory properties have been scarce. The aim of this work was to use in vivo models to evaluate the analgesic and anti-inflammatory activities of the aqueous
Robert Domitrović et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 51, 370-378 (2012-11-03)
The aim of this study was to investigate the therapeutic potential of rosmarinic acid (RA), a natural phenolic, in the treatment of acute liver toxicity. RA at 10, 25 and 50mg/kg was administered by gavage once daily for 2 consecutive
Maike Petersen et al.
Phytochemistry, 70(15-16), 1663-1679 (2009-06-30)
Rosmarinic acid and chlorogenic acid are caffeic acid esters widely found in the plant kingdom and presumably accumulated as defense compounds. In a survey, more than 240 plant species have been screened for the presence of rosmarinic and chlorogenic acids.
Kazunori Sasaki et al.
Behavioural brain research, 238, 86-94 (2012-10-23)
Rosmarinus officinalis (R. officinalis), a culinary aromatic and medicinal plant, is very rich in polyphenols and flavonoids with high antioxidant properties. This plant was reported to exert multiple benefits for neuronal system and alleviate mood disorder. In our previous study
Pedro L Falé et al.
Food & function, 4(3), 426-431 (2012-12-12)
Herbal teas are usually complex mixtures of therapeutically active compounds. The present study is focused on the interference of flavonoids on the bioavailability of rosmarinic acid, as these types of compounds are often present together in decoctions of medicinal plants
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