Methyl rosmarinate

Base Information

• Chemical Name: Methyl rosmarinate
• CAS No.: 99353-00-1
• Molecular Formula: C19H18O8
• Molecular Weight: 374.347
• DSSTox Substance ID: DTXSID901316093
• Nikkaji Number: J589.608H
• Wikidata: Q104888799
• Pharos Ligand ID: Q6DDF84W221G
• Metabolomics Workbench ID: 129005
• ChEMBL ID: CHEMBL241405
• Mol file: 99353-00-1.mol

Synonyms:Methyl rosmarinate;99353-00-1;methyl (2R)-3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxypropanoate;CHEMBL241405;(R)-3-(3,4-Dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl (E)-3-(3,4-dihydroxyphenyl)acrylate;Benzenepropanoic acid,a-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxy-,methyl ester, (aR)-;Methylrosmarinic acid;(+)-Methyl rosmarinate;Boc-L-Lysinyl-L-Proline;SCHEMBL12410151;CHEBI:175804;DTXSID901316093;HY-N3266;BDBM50210054;AKOS037515147;AS-83668;CS-0023747;F82128;(R,E)-3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl 3-(3,4-dihydroxyphenyl)acrylate;(R)-3-(3,4-Dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl(E)-3-(3,4-dihydroxyphenyl)acrylate;3-(3,4-dihydroxy-phenyl)-acrylic acid 2-(3,4-dihydroxy-phenyl)-1-methoxy carbonyl-ethyl ester;Benzenepropanoic acid, .alpha.-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxy-, methyl ester, (.alpha.R)-;methyl (2R)-3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-propanoate

Chemical Property of Methyl rosmarinate

Chemical Property:

• Boiling Point: 655.4±55.0 °C(Predicted)
• PKA: 9.29±0.10(Predicted)
• PSA: 133.52000
• Density: 1.449±0.06 g/cm3(Predicted)
• LogP: 1.84970
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 374.10016753
• Heavy Atom Count: 27
• Complexity: 534

Purity/Quality:

98%Min ^*data from raw suppliers

Methyl rosmarinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CC1=CC(=C(C=C1)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O
• Isomeric SMILES: COC(=O)[C@@H](CC1=CC(=C(C=C1)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O
• Uses: Methyl Rosmarinate is a novel S6K1 inhibitor, used as a therapeutic agent against cervical cancer.Methyl Rosmarinate is a noncompetitive tyrosinase inhibitor which is isolated from Rabdosia serra. An inhibitor of a-glucosidase

Technology Process of Methyl rosmarinate

There total 8 articles about Methyl rosmarinate 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: 93.0%

methanol (67-56-1) + (R)-(+)-rosmarinic acid (20283-92-5) → rosmarinic acid methyl ester (99353-00-1)

Guidance literature:

With thionyl chloride; at 0 ℃; for 18h;

DOI:10.1016/j.bmc.2006.06.059

Reference yield:

(R)-(+)-rosmarinic acid (20283-92-5) + diazomethyl-trimethyl-silane (18107-18-1) → rosmarinic acid methyl ester (99353-00-1)

Guidance literature:

In tetrahydrofuran; methanol; diethyl ether; at -78 - 25 ℃; for 2h; chemoselective reaction; Inert atmosphere;

Reference yield:

(E)-3-(3,4-Bis-benzyloxy-phenyl)-acrylic acid (R)-2-(3,4-bis-benzyloxy-phenyl)-1-methoxycarbonyl-ethyl ester (203798-85-0) → rosmarinic acid methyl ester (99353-00-1)

Guidance literature:

With boron trichloride; In dichloromethane; at -78 ℃; Yield given;

DOI:10.1007/pl00010154

upstream raw materials:

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

methanol

(R)-(+)-rosmarinic acid

(+)-(S)-methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate

Downstream raw materials:

C₅₁H₃₈F₁₂O₈

rosmarinic acid permethylate

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

methyl (E)-3-(3,4-bis(benzyloxy)phenyl)acrylate

Refernces

• 1、 Zhu, Fengxian,Xu, Zhongming,Yonekura, Lina,Yang, Ronghua,Tamura, Hirotoshi. "Antiallergic activity of rosmarinic acid esters is modulated by hydrophobicity, and bulkiness of alkyl side chain". . p. 1178 - 1182. Retrieved 2015/10/05.
• 2、 Panya, Atikorn,Kittipongpittaya, Ketinun,Laguerre, Micka?l,Bayrasy, Christelle,Lecomte, Jér?me,Villeneuve, Pierre,McClements, D. Julian,Decker, Eric A.. "Interactions between α-tocopherol and rosmarinic acid and its alkyl esters in emulsions: Synergistic, additive, or antagonistic effect?". . p. 10320 - 10330. Retrieved 2013/01/15.