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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/REAXYS Number:
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

11 - Combustible Solids

wgk_germany

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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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
Victor P Bulgakov et al.
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
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
Eun-Ju Yang et al.
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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