Methyl rosmarinateCAS# 99353-00-1 |
Quality Control & MSDS
3D structure
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| Cas No. | 99353-00-1 | SDF | Download SDF |
| PubChem ID | 6479915 | Appearance | Powder |
| Formula | C19H18O8 | M.Wt | 374.4 |
| Type of Compound | Phenylpropanoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | methyl (2R)-3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxypropanoate | ||
| SMILES | COC(=O)C(CC1=CC(=C(C=C1)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O | ||
| Standard InChIKey | XHALVRQBZGZHFE-BBOMDTFKSA-N | ||
| Standard InChI | InChI=1S/C19H18O8/c1-26-19(25)17(10-12-3-6-14(21)16(23)9-12)27-18(24)7-4-11-2-5-13(20)15(22)8-11/h2-9,17,20-23H,10H2,1H3/b7-4+/t17-/m1/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Methyl rosmarinate shows antioxidative, and antifungal activities. It has inhibitory activities against tyrosinase, α-glucosidase, and matrix metalloproteinase-1 (MMP-1). |
| Targets | Tyrosinase | Antifection | MMP(e.g.TIMP) |
| In vitro | Impact of fatty acid chain length of rosmarinate esters on their antimicrobial activity against Staphylococcus carnosus LTH1502 and Escherichia coli K-12 LTH4263.[Pubmed: 23992498 ]J Food Prot. 2013 Sep;76(9):1539-48.The effect of the addition of a newly synthesized series of rosmarinic acid (RA) estes (REs) and alcohols with chain lengths of 1, 4, 8, 10, 12, 16, and 18 carbons (RE1 to 18) on the growth behavior of Staphylococcus carnosus LTH1502 and Escherichia coli K-12 LTH4263 was investigated. [Chemical constituents of Hyptis rhomboidea and their antifungal activity].[Pubmed: 25244760]Zhongguo Zhong Yao Za Zhi. 2014 Jun;39(12):2284-8.The present work is to investigate the chemical constitutions of Hyptis rhomboidea and their antifungal activities. |
| Kinase Assay | Comparative evaluation of rosmarinic acid, methyl rosmarinate and pedalitin isolated from Rabdosia serra (MAXIM.) HARA as inhibitors of tyrosinase and α-glucosidase.[Pubmed: 25212314]Food Chem. 2011 Dec 1;129(3):884-9.Rabdosia serra has been used in traditional Chinese medicine for centuries. In order to illustrate the pharmaceutical activity of R. serra as hypoglycaemic and skin-whitening agents, rosmarinic acid (confirmed as the major compound in R. serra), Methyl rosmarinate and pedalitin isolated from R. serra were evaluated for their inhibitory effects and mechanisms on tyrosinase and α-glucosidase. |
| Structure Identification | Eur J Med Chem. 2013 Apr;62:148-57.Synthesis of derivatives of methyl rosmarinate and their inhibitory activities against matrix metalloproteinase-1 (MMP-1).[Pubmed: 23353736]
Arch Pharm Res. 2004 Feb;27(2):173-6.Antioxidative constituents from Lycopus lucidus.[Pubmed: 15022718]Three phenolic compounds, rosmarinic acid (1), Methyl rosmarinate (2), ethyl rosmarinate (3), and two flavonoids, luteolin (4), luteolin-7-O-beta-D-glucuronide methyl ester (5) were isolated from the aerial part of Lycopus lucidus (Labiatae). |
Methyl rosmarinate Dilution Calculator
Methyl rosmarinate Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.6709 mL | 13.3547 mL | 26.7094 mL | 53.4188 mL | 66.7735 mL |
| 5 mM | 0.5342 mL | 2.6709 mL | 5.3419 mL | 10.6838 mL | 13.3547 mL |
| 10 mM | 0.2671 mL | 1.3355 mL | 2.6709 mL | 5.3419 mL | 6.6774 mL |
| 50 mM | 0.0534 mL | 0.2671 mL | 0.5342 mL | 1.0684 mL | 1.3355 mL |
| 100 mM | 0.0267 mL | 0.1335 mL | 0.2671 mL | 0.5342 mL | 0.6677 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Synthesis of derivatives of methyl rosmarinate and their inhibitory activities against matrix metalloproteinase-1 (MMP-1).[Pubmed:23353736]
Eur J Med Chem. 2013 Apr;62:148-57.
A series of MMP-1 inhibitors have been identified based upon a Methyl rosmarinate scaffold using structure-based drug design methods. The best compound in the series showed an IC50 value of 0.4 muM. A docking study was conducted for compound (S)-10n in order to investigate its binding interactions with MMP-1. The structure-activity relationships (SAR) were also briefly discussed. Useful SAR was established which provides important guidelines for the design of future generations of potent inhibitors against MMP-1.
Comparative evaluation of rosmarinic acid, methyl rosmarinate and pedalitin isolated from Rabdosia serra (MAXIM.) HARA as inhibitors of tyrosinase and alpha-glucosidase.[Pubmed:25212314]
Food Chem. 2011 Dec 1;129(3):884-9.
Rabdosia serra has been used in traditional Chinese medicine for centuries. In order to illustrate the pharmaceutical activity of R. serra as hypoglycaemic and skin-whitening agents, rosmarinic acid (confirmed as the major compound in R. serra), Methyl rosmarinate and pedalitin isolated from R. serra were evaluated for their inhibitory effects and mechanisms on tyrosinase and alpha-glucosidase. The inhibitory effects on both tyrosinase and alpha-glucosidase were in decreasing order, pedalitin>Methyl rosmarinate>rosmarinic acid. The IC50 values for the tyrosinase and alpha-glucosidase activity inhibited by pedalitin were 0.28 and 0.29mM, respectively. Both rosmarinic acid and Methyl rosmarinate were considered as noncompetitive inhibitors of tyrosinase, while pedalitin was suggested to be a mixed-type inhibitor of tyrosinase. In the assay of alpha-glucosidase inhibition, rosmarinic acid was found to be a competitive inhibitor, whereas both Methyl rosmarinate and pedalitin were considered as mixed-type inhibitors.
Impact of fatty acid chain length of rosmarinate esters on their antimicrobial activity against Staphylococcus carnosus LTH1502 and Escherichia coli K-12 LTH4263.[Pubmed:23992498]
J Food Prot. 2013 Sep;76(9):1539-48.
The effect of the addition of a newly synthesized series of rosmarinic acid (RA) estes (REs) and alcohols with chain lengths of 1, 4, 8, 10, 12, 16, and 18 carbons (RE1 to 18) on the growth behavior of Staphylococcus carnosus LTH1502 and Escherichia coli K-12 LTH4263 was investigated. An initial microtiter dilution assay indicated activity of compounds against S. carnosus LTH1502, whereas esters with chain lengths, RA, n-Methyl rosmarinate (RE1), n-dodecyl rosmarinate (RE12), and n-octadecyl rosmarinate (RE18) were used in a time-kill assay S. carnosus LTH1502. Compounds were added at 0.75 mM in the log phase, 5 mM in the exponential phase, 10 mM in the stationary phase. RA had no effect in the lag and exponential phase but decreased cell counts during the stationary phase. In contrast, RE1 and RE12 decreased cell number in all three phase, will RE12 reducing counts most rapidly. Addition of RE18 did not affect regardless of the growth phase. Appearance and physiological state of S. carnosus LTH1502 cells indicated difference in the way the compounds interacted with and damaged cells. Results were attributed to the different physicochemical properties of RA and its esters.
[Chemical constituents of Hyptis rhomboidea and their antifungal activity].[Pubmed:25244760]
Zhongguo Zhong Yao Za Zhi. 2014 Jun;39(12):2284-8.
The present work is to investigate the chemical constitutions of Hyptis rhomboidea and their antifungal activities. The compounds were isolated by Toyopearl HW-40, Sephadex LH-20, MCI-Gel CHP-20, RP-18, PTLC and silica column chromatographic methods and subjected to evaluate some monomers antifungal activity of eight kinds of plant pathogenic bacteria. Eleven compounds were isolated and identified as ethyl caffeate (1), ursolic acid (2), oleanolic acid (3), vanillactic acid (4), Methyl rosmarinate (5), kaempferol 3-O-alpha-L-rhamnopyranosyl-(1 --> 6) -beta-D-glucopyranoside (6), kaempferol 3-O-alpha-L-rhamnopyranosyl-(1 --> 6)-beta-D-glucopyranoside (7), ilexgenin A (8), beta-amyrin (9), kaempferol 3-O-beta-D-glucopyranoside (astrgalin, 10) and cholest-5-ene-3beta, 4beta-diol (11). Compound 1 showed the strongest inhibitory effect on Sclerotinia sclerotiorum with the MIC 16.2 mg x L(-1), and compound 5 showed the strongest inhibitory effect on S. minor and Exserohilum turcicum with MIC 16.2, 8.1 mg x L(-1), respectively. All compounds were isolated from the H. rhomboidea for the first time, and compounds 1 and 5 showed antifungal activity.
Antioxidative constituents from Lycopus lucidus.[Pubmed:15022718]
Arch Pharm Res. 2004 Feb;27(2):173-6.
Three phenolic compounds, rosmarinic acid (1), Methyl rosmarinate (2), ethyl rosmarinate (3), and two flavonoids, luteolin (4), luteolin-7-O-beta-D-glucuronide methyl ester (5) were isolated from the aerial part of Lycopus lucidus (Labiatae). Their structures were determined by chemical and spectral analysis. Compounds 1-5 exhibited potent antioxidative activity on the NBT superoxide scavenging assay. The IC50 values for compounds 1-5 were 2.59, 1.42, 0.78, 2.83, and 3.05 microg/mL respectively. In addition, five compounds were isolated from this plant for the first time.
