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00390580

Acide rosmarinique

primary reference standard

Synonyme(s) :

Acide (R)-O-(3,4-Dihydroxycinnamoyl)-3-(3,4- dihydroxyphényl)lactique, Ester (R)-1-carboxy-2-(3,4-dihydroxyphényl)éthylique d’acide 3,4-Dihydroxycinnamique

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About This Item

Formule empirique (notation de Hill):
C18H16O8
Numéro CAS:
20283-92-5
Poids moléculaire :
360.31
Numéro Beilstein :
2227587
Numéro MDL:
MFCD00017740
Code UNSPSC :
85151701
ID de substance PubChem :
329747058
Nomenclature NACRES :
NA.24

Qualité

primary reference standard

Durée de conservation

limited shelf life, expiry date on the label

Fabricant/nom de marque

HWI

Technique(s)

HPLC: suitable
gas chromatography (GC): suitable

Pf

171-175 °C (lit.)

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

DOUMFZQKYFQNTF-WUTVXBCWSA-N

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Description générale

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.

Actions biochimiques/physiologiques

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.

Autres remarques

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (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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