R4033

Sigma-Aldrich

Rosmarinic acid

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

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/REAXYS Number:
2227587
MDL number:
PubChem Substance ID:

biological source

Rosemarinus officinalis L.

Quality Level

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

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

Packaging

10, 50 mg in glass bottle

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.
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

6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Certificate of Analysis

Certificate of Origin

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...
Polyphenols analysis from different medicinal plants extracts using capillary zone electrophoresis (CZE)
Matei AO, et al.,
Revista de Chimie, 67, 1051-1105 (2016)
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...
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...
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...

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