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00390580

Rosmarinic acid

primary reference standard

Synonym(s):
3,4-Dihydroxycinnamic acid (R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethyl ester, (R)-O-(3,4-Dihydroxycinnamoyl)-3-(3,4- dihydroxyphenyl)lactic acid
Empirical Formula (Hill Notation):
C18H16O8
CAS Number:
Molecular Weight:
360.31
Beilstein:
2227587
MDL number:
PubChem Substance ID:
NACRES:
NA.24

grade

primary reference standard

shelf life

limited shelf life, expiry date on the label

manufacturer/tradename

HWI

application(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, anti-inflammatory and antimicrobial activities. Possesses promising physiological actions related to cognitive performance, Alzheimer′s disease prevention, kideney disease treatment, cardioprotection and cancer chemoprevention.

Storage Class Code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Cristina Airoldi et al.
Chemistry, an Asian journal, 8(3), 596-602 (2013-01-11)
Amyloid peptides, Aβ1-40 and Aβ1-42, represent major molecular targets to develop potential drugs and diagnostic tools for Alzheimer's Disease (AD). In fact, oligomeric and fibrillar aggregates generated by these peptides are amongst the principal components of amyloid plaques found post...
Anja Klančnik et al.
PloS one, 7(12), e51800-e51800 (2013-01-04)
Campylobacter is a major foodborne pathogen and alternative antimicrobials are needed to prevent or decrease Campylobacter contamination in foods or food producing animals. The objectives of this study are to define the anti-Campylobacter activities of natural phenolic compounds of plant...
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...
Juan A Martín et al.
PloS one, 8(2), e56987-e56987 (2013-03-08)
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...
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...

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