R4033

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
• 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

Properties

• biological source: Rosemarinus officinalis L.
• Quality Level: 100
• 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

Description

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable