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R4033

Sigma-Aldrich

Rosmarinic acid

≥98% (HPLC), from Rosemarinus officinalis L.

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:
12352106
PubChem Substance ID:
329824027
NACRES:
NA.25

biological source

Rosemarinus officinalis L.

assay

≥98% (HPLC)

form

powder

storage condition

protect from light

color

white to faint beige

mp

171-175 °C (lit.)

solubility

H2O: 1 mg/mL, clear, colorless

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°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

Rosmarinic acid is a naturally occurring polyphenolic compound found in plants of the Boraginaceae family and Nepetoideae subfamily. It is an ester of caffeic acid as well as 3,4-dihydroxy-phenyllactic acid.

Application

Rosmarinic acid has been used:
  • to see its protective effects on the human endothelial cell line (EA.hy926) to treat diabetic atherosclerosis
  • to test its effect in 1-Methyl-4-phenyl-1, 2, 3, 6-tetrahydropyridine (MPTP) induced Parkinson′s disease (PD) models on attenuating inflammatory responses and microglia activation
  • to test its neuroprotective effects on dopaminergic neurons
  • to test its effects on sperm motility, viability and on intracellular calcium ion concentration
  • as a reference standard in capillary zone electrophoresis (CZE) method

Biochem/physiol Actions

Rosmarinic acid (RosA) is a well-appreciated agent used in several diabetic conditions and complications such as diabetic nephropathy, diabetic neuropathy and diabetic atherosclerosis. It has also been implicated to be a neuroprotective agent for several neurological disorders such as Alzheimer′s disease, Parkinson′s disease, and epilepsy by suppressing their conditions.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Meng-Ge Lv et al.
Reproductive toxicology (Elmsford, N.Y.), 81, 58-63 (2018-07-17)
Rosmarinic acid (RA), a natural phenolic ester, is cytoprotective for male reproduction in animal models. The present study investigated the in vitro actions of RA on human sperm functions. Human sperm were exposed to 1, 10, 100, and 1000 μM
Polyphenols analysis from different medicinal plants extracts using capillary zone electrophoresis (CZE)
Matei AO, et al.,
Revista de Chimie, 67, 1051-1105 (2016)
A Oğuz et al.
Folia morphologica, 79(2), 288-295 (2019-08-23)
The aim of the study was to investigate the protective effects of rosmarinic acid in rats exposed to hepatic ischaemia/reperfusion (I/R) injury. Thirty-two rats were randomly classified into four groups of 8 rats each: laparotomy without medication, rosmarinic acid (dose
Tomoki Hase et al.
Scientific reports, 9(1), 8711-8711 (2019-06-20)
A new mechanism is revealed by which a polyphenol, rosmarinic acid (RA), suppresses amyloid β (Aβ) accumulation in mice. Here we examined the brains of mice (Alzheimer's disease model) using DNA microarray analysis and revealed that the dopamine (DA)-signaling pathway
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
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