CAS Number20283-92-5
SynonymsR-(+)-2-(3,4-Dihydroxycinnamoyloxy)-3-(3,4-dihydroxyphenyl)propionic acid; MFCD00017740; ROSMARINATE; (R)-rosmarinic acid; (+)-Rosmarinic acid; Rosemary acid; (2R)-3-(3,4-Dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid; (2R)-3-(3,4-Dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]oxy}propanoic acid; RosmarinicAcid; Rosmarinic acid; rosemaryacid; Rosmarinic; Rosemaricacid; Labiatenic acid; 3,4-Dihydroxycinnamicacid(R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethylester; (R)-O-(3,4-Dihydroxycinnamoyl)-3-(3,4-dihydroxyphenyl)lacticacid; 4-dihydroxy
Molecular FormulaC18H16O8
Molecular Weight360.31
Purity≥98 (HPLC)%
Density1.5±0.1 g/cm3
Boiling Point694.7±55.0 °C at 760 mmHg
Melting Point171-175 °C (lit.)
Appearancepowder
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 20283-92-5 |
| Catalog No. | 2A-9012345 |
| Chinese Name | 迷迭香酸 |
| Synonyms | R-(+)-2-(3,4-Dihydroxycinnamoyloxy)-3-(3,4-dihydroxyphenyl)propionic acid; MFCD00017740; ROSMARINATE; (R)-rosmarinic acid; (+)-Rosmarinic acid; Rosemary acid; (2R)-3-(3,4-Dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid; (2R)-3-(3,4-Dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]oxy}propanoic acid; RosmarinicAcid; Rosmarinic acid; rosemaryacid; Rosmarinic; Rosemaricacid; Labiatenic acid; 3,4-Dihydroxycinnamicacid(R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethylester; (R)-O-(3,4-Dihydroxycinnamoyl)-3-(3,4-dihydroxyphenyl)lacticacid; 4-dihydroxy |
| Molecular Formula | C18H16O8 |
| Molecular Weight | 360.31 |
| Purity | ≥98 (HPLC) |
| Density | 1.5±0.1 g/cm3 |
| Boiling Point | 694.7±55.0 °C at 760 mmHg |
| Melting Point | 171-175 °C (lit.) |
| Appearance | powder |
| Storage Condition | Dry, cool, sealed place, in inert gas |
| Application | Rosmarinic acid is a natural polyphenol with antioxidant and anti-inflammatory activities. |
| HTC | 2932999099 |
| PubChem ID | 329824027 |
| MDL Number | MFCD00017740 |
| SMILES | 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 |
| Beilstein/REAXYS | 2227587 |
| NACRES Code | NA.25 |
| UNSPSC | 12352106 |
| Hazard Symbols | Transport |
| MSDS | msds/12345_1_20283_92_5.pdf |
| Bioactivity | Rosmarinic acid (RA) is a widespread phenolic ester compound in the plants. Rosmarinic acid inhibits MAO-A, MAO-B and COMT enzymes with IC50s of 50.1, 184.6 and 26.7 μM, respectively. Related Catalog Signaling Pathways >> Neuronal Signaling >> Monoamine Oxidase Research Areas >> Others Natural Products >> Terpenoids and Glycosides Target IC50: 50.1 μM (MAO-A), 184.6 μM (MAO-B), 26.7 μM (COMT)[1] In Vitro Rosmarinic acid (RA) shows an in vitro multifunctional profile characterized by antioxidant effects, and monoamine oxidases (MAO-A and MAO-B) and catechol-O-methyl transferase (COMT) inhibition. Rosmarinic acid shows antioxidant effects against hydroxyl (HO(•)) and nitric oxide (NO) radicals (IC50 of 29.4 and 140 μM, respectively), and inhibition of lipid peroxidation (IC50 of 19.6 μM)[1]. Rosmarinic acid (RA) exerts a significant cytoprotective effect by scavenging intracellular ROS induced by UVB. In H2O2-treated cells, 2.5 μM Rosmarinic acid scavenges 60% of intracellular ROS compared to 77% of intracellular ROS scavenging effect in N-acetyl-L-cysteine (NAC)[2]. In Vivo Rosmarinic acid (RA) is a widespread phenolic ester compound in the plants, particularly those in the Labiatae family of herbs, such as Rosmarinus officinali, Salvia miltiorrhiza, and Prunella vulgaris. Rosmarinic acid suppresses colonic inflammation in dextran sulphate sodium (DSS)-induced mice via dual inhibition of NF-κB and STAT3 activation. In the DSS-induced colitis model, Treatment with Rosmarinic acid (30, 60 mg/kg, p.o.) markedly attenuates the production of cytokines[3]. Cell Assay Human keratinocytes (HaCaT cells) are treated with Rosmarinic acid (0.625, 1.25, 2.5, or 5 μM) and exposed to UVB radiation 1 h later. They are then incubated at 37°C for 48 h. At this time, MTT is added to each well to obtain a total reaction volume of 200 μL. After 4 h incubation, the supernatant is removed by aspiration. The formazan crystals in each well are dissolved in dimethyl sulfoxide (DMSO; 150 μL), and the absorbance at 540 nm is measured on a scanning multi-well spectrophotometer[2]. Animal Admin Mice[3] Experimental colitis is induced by giving mice drinking water ad libitum containing 5% (w/v) DSS for 7 days. Mice of each of the groups are monitored carefully every day to confirm that they have consumed an approximately equal volume of water containing DSS. For each experiment, the mice are divided into five experimental groups (n = 10/group). The first group is kept as the vehicle-treated control, and the second group is given drinking water with DSS only during the experimental period. The other three groups consist of mice receiving 5% DSS who are administrated 5-ASA (75 mg/kg/day p.o.) or Rosmarinic acid (30 or 60 mg/kg/day p.o.) daily for 7 days. Control groups are given the vehicle daily for 7 days as appropriate. Administration of each drug is initiated simultaneously with the DSS treatment. References [1]. Andrade JM, et al. Combining in vitro and in silico approaches to evaluate the multifunctional profile of rosmarinic acid from Blechnum brasiliense on targets related to neurodegeneration. Chem Biol Interact. 2016 Jul 25;254:135-45. [2]. Fernando PM, et al. Rosmarinic Acid Attenuates Cell Damage against UVB Radiation-Induced Oxidative Stress via Enhancing Antioxidant Effects in Human HaCaT Cells. Biomol Ther (Seoul). 2016 Jan;24(1):75-84. [3]. Jin BR, et al. Rosmarinic acid suppresses colonic inflammation in dextran sulphate sodium (DSS)-induced mice via dual inhibition of NF-κB and STAT3 activation. Sci Rep. 2017 Apr 6;7:46252. Chemical & Physical Properties Density 1.5±0.1 g/cm3 Boiling Point 694.7±55.0 °C at 760 mmHg Melting Point 171-175 °C(lit.) Molecular Formula C18H16O8 Molecular Weight 360.315 Flash Point 254.5±25.0 °C Exact Mass 360.084503 PSA 144.52000 LogP 1.70 Vapour Pressure 0.0±2.3 mmHg at 25°C Index of Refraction 1.714 InChIKey DOUMFZQKYFQNTF-WUTVXBCWSA-N SMILES O=C(C=Cc1ccc(O)c(O)c1)OC(Cc1ccc(O)c(O)c1)C(=O)O Storage condition Store at RT |
| Use of | Rosmarinic acid (RA) is a widespread phenolic ester compound in the plants. Rosmarinic acid inhibits MAO-A, MAO-B and COMT enzymes with IC50s of 50.1, 184.6 and 26.7 μM, respectively. Properties Articles95 Name rosmarinic acid Synonym More Synonyms Rosmarinic acid Biological Activity Description Rosmarinic acid (RA) is a widespread phenolic ester compound in the plants. Rosmarinic acid inhibits MAO-A, MAO-B and COMT enzymes with IC50s of 50.1, 184.6 and 26.7 μM, respectively. Related Catalog Signaling Pathways >> Neuronal Signaling >> Monoamine Oxidase Research Areas >> Others Natural Products >> Terpenoids and Glycosides IC50: 50.1 μM (MAO-A), 184.6 μM (MAO-B), 26.7 μM (COMT)[1] In Vitro Rosmarinic acid (RA) shows an in vitro multifunctional profile characterized by antioxidant effects, and monoamine oxidases (MAO-A and MAO-B) and catechol-O-methyl transferase (COMT) inhibition. Rosmarinic acid shows antioxidant effects against hydroxyl (HO(•)) and nitric oxide (NO) radicals (IC50 of 29.4 and 140 μM, respectively), and inhibition of lipid peroxidation (IC50 of 19.6 μM)[1]. Rosmarinic acid (RA) exerts a significant cytoprotective effect by scavenging intracellular ROS induced by UVB. In H2O2-treated cells, 2.5 μM Rosmarinic acid scavenges 60% of intracellular ROS compared to 77% of intracellular ROS scavenging effect in N-acetyl-L-cysteine (NAC)[2]. References [1]. Andrade JM, et al. Combining in vitro and in silico approaches to evaluate the multifunctional profile of rosmarinic acid from Blechnum brasiliense on targets related to neurodegeneration. Chem Biol Interact. 2016 Jul 25;254:135-45. [2]. Fernando PM, et al. Rosmarinic Acid Attenuates Cell Damage against UVB Radiation-Induced Oxidative Stress via Enhancing Antioxidant Effects in Human HaCaT Cells. Biomol Ther (Seoul). 2016 Jan;24(1):75-84. [3]. Jin BR, et al. Rosmarinic acid suppresses colonic inflammation in dextran sulphate sodium (DSS)-induced mice via dual inhibition of NF-κB and STAT3 activation. Sci Rep. 2017 Apr 6;7:46252. Chemical & Physical Properties Molecular Formula C18H16O8 Exact Mass 360.084503 PSA 144.52000 Index of Refraction 1.714 InChIKey DOUMFZQKYFQNTF-WUTVXBCWSA-N Storage condition Store at RT |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available See reverse side of invoice or packing slip. |
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