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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:
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

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

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Certificate of Origin

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