Rosmarinic acid

Base Information

• Chemical Name: Rosmarinic acid
• CAS No.: 20283-92-5
• Molecular Formula: C18H16O8
• Molecular Weight: 360.32
• Hs Code.: 29189900
• Mol file: 20283-92-5.mol

Synonyms:Benzenepropanoicacid, a-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-3,4-dihydroxy-,(aR)-;Benzenepropanoicacid, a-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxy-,(aR)- (9CI);Benzenepropanoic acid, a-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxy-,[R-(E)]-;Cinnamic acid, 3,4-dihydroxy-, 2-ester with3-(3,4-dihydroxyphenyl)lactic acid;Rosmarinic acid (6CI,7CI);MamorekkuRUH 2;RM 21A;trans-Rosmarinic acid;

Chemical Property of Rosmarinic acid

Chemical Property:

• Appearance/Colour: Brown fine powder
• Vapor Pressure: 2.92E-20mmHg at 25°C
• Melting Point: 171-175 °C(lit.)
• Refractive Index: 1.713
• Boiling Point: 694.7 °C at 760 mmHg
• PKA: 2.78±0.10(Predicted)
• Flash Point: 254.5 °C
• PSA: 144.52000
• Density: 1.547 g/cm³
• LogP: 1.76130
• Storage Temp.: Store at RT
• Solubility.: H2O: soluble1mg/mL, clear, colorless

Purity/Quality:

95%-98% ^*data from raw suppliers

Rosmarinic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

Useful:

• Uses: 1. Rosmarinic acid is an ester of caffeic acid and 3,4-dihydroxyphenyllactic acid. It is commonly found in species of the Boraginaceae and the subfamily Nepetoideae of the Lamiaceae. However, it is also found in species of other higher plant families and in some fern and hornwort species. Rosmarinic acid has a number of interesting biological activities, e.g. antiviral, antibacterial, antiinflammatory and antioxidant. The presence of rosmarinic acid in medicinal plants, herbs and spices has beneficial and health promoting effects. In plants, rosmarinic acid is supposed to act as a preformed constitutively accumulated defence compound.[sciencedirect] 2. Rosmarinic acid (RA) is one example of a naturally occurring phenolic compound in plants. RA is especially high in Salvia officinalis (garden sage). As an antioxidant, RA possesses both health benefits, and is useful as a food additive to keep foods fresh.Recently, Bakota et al. successfully prepared an extract of Salvia officinalis at three times the levels from sage leaves alone.[thermofisher] 3. Rosmarinic Acid is a phenylpropanoid isolated from Labiatae herbs. The compound exhibits antiinflammatory activity and inhibits the proliferation of murine mesangial cells. Rosmarinic Acid has been shown to dose dependently inhibit migration, adhesion, and invasion of Ls174-T human colon carcinoma cells. Rosmarinic Acid has been documented to increase the melanin content in B16 melanoma cells through activation of protein kinase A. In the same study rosmarinic acid induced the phosphorylation of CRE-binding protein (CREB) and activated cAMP response element (CRE). In the classical complement pathway Rosmarinic Acid inhibited C3-convertase. It also has shown to be an activator of GPR35.[Santa Cruz] 4. Rosmarinic acid is a naturally-occurring phenolic compound with antioxidant and anti-inflammatory properties. This compound inhibits lipid peroxidation of rat liver microsomes by 90% at a concentration of 25 μg/ml.Rosmarinic acid suppresses endotoxin-induced activation of complement and concomitant formation of prostacyclin.Formation of 5-HETE and LTB from human PMNL is inhibited by rosmarinic acid at concentrations of 10-5 to 10-3 M. [caymanchem] Rosmarinic Acid is a phenolic compound with antioxidant and anti-inflammatory activity. Rosmarinic Acid has been shown to inhibit againts peroxidative damage to biomembranes. Rosmarinic Acid also supp resses endotoxin-induced activation of complement and concomitant prostacyclin biosynthesis. An activator of GPR35. Rosmarinic acid is a naturally-occurring phenolic compound with antioxidant and anti-inflammatory properties. This compound inhibits lipid peroxidation of rat liver microsomes by 90% at a concentration of 25 μg/ml. Rosmarinic acid suppresses endotoxin-induced activation of complement and concomitant formation of prostacyclin. Formation of 5-HETE and LTB4 from human PMNL is inhibited by rosmarinic acid at concentrations of 10-5 to 10-3 M.
• Description: Rosmarinic acid (20283-92-5) displays radical scavenging1, anti-inflammatory2 and amyloid-β aggregation inhibition activities.3 Rosmarinic acid has also been shown to act as an agonist at GPR35.4

Technology Process of Rosmarinic acid

There total 20 articles about Rosmarinic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

(E)-3-(3,4-Dihydroxy-phenyl)-acrylic acid (R)-1-allyloxycarbonyl-2-(3,4-dihydroxy-phenyl)-ethyl ester (179462-78-3) → (R)-(+)-rosmarinic acid (20283-92-5)

Guidance literature:

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; Ambient temperature;

DOI:10.1055/s-1996-4289

Reference yield: 92.0%

(E)-3-(3,4-Bis-allyloxy-phenyl)-acrylic acid (R)-1-allyloxycarbonyl-2-(3,4-bis-allyloxy-phenyl)-ethyl ester (179462-77-2) → (R)-(+)-rosmarinic acid (20283-92-5)

Guidance literature:

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; Ambient temperature;

DOI:10.1055/s-1996-4289

Reference yield:

→ Rosmarinic acid (20283-92-5,537-15-5)

Guidance literature:

Synthese mit Hilfe von Zellkulturen von Colens blumei;

DOI:10.1007/BF00450645

upstream raw materials:

danshensu

caffeic acid coenzyme A thiol ester

(E)-3-(3,4-Dihydroxy-phenyl)-acrylic acid (R)-1-allyloxycarbonyl-2-(3,4-dihydroxy-phenyl)-ethyl ester

(E)-3-(3,4-Bis-allyloxy-phenyl)-acrylic acid (R)-1-allyloxycarbonyl-2-(3,4-bis-allyloxy-phenyl)-ethyl ester

Downstream raw materials:

C₁₈H₁₅NO₁₀

C₁₈H₁₄N₂O₁₂

C₂₀H₁₈O₁₀

rosmarinic acid permethylate

Refernces

• 1、 Eicher, Theophil,Ott, Markus,Speicher, Andreas. "Bryophyte constituents; 7: New synthesis of (+)-rosmarinic acid and related compounds". . p. 755 - 762. Retrieved 2007/10/03.