174591-47-0

Usage

Uses

Used in Health Applications:
Ethyl ester of rosmarinic acid is used as a therapeutic agent for its antioxidant and anti-inflammatory properties, helping to protect against oxidative damage and inflammation in cells and tissues.
Used in Cosmetic Applications:
Ethyl ester of rosmarinic acid is used as an ingredient in skincare products for its ability to protect against skin damage caused by UV radiation and environmental pollutants, contributing to skin health and appearance.
Used in Pharmaceutical Applications:
Ethyl ester of rosmarinic acid is used as a potential therapeutic agent in the development of new drugs, leveraging its antioxidant and anti-inflammatory properties for the treatment of various conditions.
Used in Food Industry:
Ethyl ester of rosmarinic acid is used as a natural preservative and flavor enhancer in the food industry, capitalizing on its antioxidant properties to extend shelf life and improve taste.
Used in Agricultural Applications:
Ethyl ester of rosmarinic acid is used in agriculture as a natural pesticide or growth promoter, taking advantage of its antioxidant and anti-inflammatory properties to protect crops and enhance growth.

Upstream product

• 64-17-5 ethanol 
• 179462-74-9 rosmarinic acid 
• 20283-92-5 (R)-(+)-rosmarinic acid 

Relevant academic research and scientific papers

Ethyl rosmarinate relaxes rat aorta by an endothelium-independent pathway

Ethyl rosmarinate is an ester derivative of rosmarinic acid, a major constituent of Hyptis suaveolens. The present study investigated the vasorelaxant mechanism of ethyl rosmarinate in isolated rat aortic rings using an organ bath system. Ethyl rosmarinat

Ethyl rosmarinate inhibits lipopolysaccharide-induced nitric oxide and prostaglandin E2 production in alveolar macrophages

In this study, a series of rosmarinic acid and analogs were investigated for their anti-inflammatory potential against LPS-induced alveolar macrophages (MH-S). Our results showed that, among the test compounds, ethyl rosmarinate (3) exhibited the most pot

Short Chain (≤C4) Esterification Increases Bioavailability of Rosmarinic Acid and Its Potency to Inhibit Vascular Smooth Muscle Cell Proliferation

Rosmarinic acid is a natural phenolic acid and active compound found in many culinary plants, such as rosemary, mint, basil and perilla. Aiming to improve the pharmacokinetic profile of rosmarinic acid and its activity on vascular smooth muscle cell proliferation, we generated a series of rosmarinic acid esters with increasing alkyl chain length ranging from C1 to C12. UHPLC-MS/MS analysis of rat blood samples revealed the highest increase in bioavailability of rosmarinic acid, up to 10.52%, after oral administration of its butyl ester, compared to only 1.57% after rosmarinic acid had been administered in its original form. When added to vascular smooth muscle cells in vitro, all rosmarinic acid esters were taken up, remained esterified and inhibited vascular smooth muscle cell proliferation with IC50 values declining as the length of alkyl chains increased up to C4, with an IC50 of 2.84?μM for rosmarinic acid butyl ester, as evident in a resazurin assay. Vascular smooth muscle cells were arrested in the G0/G1 phase of the cell cycle and the retinoblastoma protein phosphorylation was blocked. Esterification with longer alkyl chains did not improve absorption and resulted in cytotoxicity in in vitro settings. In this study, we proved that esterification with proper length of alkyl chains (C1–C4) is a promising way to improve in vivo bioavailability of rosmarinic acid in rats and in vitro biological activity in rat vascular smooth muscle cells.

The structure-activity relationship of the series of non-peptide small antagonists for p56lck SH2 domain

The antagonists for the SH2 domain are regarded as novel therapeutic candidates for cancer, autoimmune disease, and chronic inflammatory disease. Previously, we identified rosmarinic acid (α-o-caffeoyl-3,4-dihydroxyphenyl-lactic acid; RosA) from Prunella vulgaris as an antagonist for the p56lck SH2 domain by screening natural products. RosA not containing phosphotyrosine surrogate had a considerable inhibitory activity for T-cell antigen receptor (TCR)-induced interleukin (IL)-2 expression, and subsequent T-cell proliferation in vitro cell assay. To investigate the structure-activity relationship of RosA and to identify a novel p56lck SH2 antagonist with more potent in vitro T-cell inhibitory activity, we synthesized several analogs of RosA by using rational design. All synthesized compounds were tested in vitro binding activity for the SH2 domain and in vitro T-cell inhibitory activity. All four hydroxyl groups of RosA were essential for binding with the p56lck SH2 domain and T-cell inhibitory activity. Unexpectedly, conformationally less constrained analogs 4 and 9 showed a more potent binding affinity for the SH2 domain than that of RosA, and chirality of the analog did not play an important role in protein binding. We successfully identified several RosA analogs with a more potent T-cell inhibitory activity than that of RosA. Overall results revealed important structural requirements of the p56lck SH2 antagonists for in vitro T-cell inhibitory activity and in vitro protein binding activity.

USE OF ROSMARINIC ACID AND DERIVATIVES THEREOF AS AN IMMUNOSUPPRESSANT OR AN INHIBITOR OF SH2-MEDIATED PROCESS

The present invention relates to use of rosmarinic acid and/or derivatives thereof as immunosuppressive agents and/or as inhibitor of SH2 domain function. Disclosed in the present invention is that rosmarinic acid and derivatives thereof specifically inhibit the binding of ligand peptides to Lck SH2 domain, disturb the Lck-mediated signal transduction in T cells, also inhibit cytoline gene expression, and suppress immune responses in the transplanted tissue. These activities of rosmarinic acid and derivatives thereof support their applicability to treatment, prevention and/or diagnosis of graft rejection, GVHD, autoimmune diseases, inflammatory diseases, etc.