Leprapinic acid methyl ether
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| Category | Others |
| Catalog number | BBF-05069 |
| CAS | 22628-25-7 |
| Molecular Weight | 366.36 |
| Molecular Formula | C21H18O6 |
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Specification
| Synonyms | Benzeneacetic acid, 2-methoxy-α-(3-methoxy-5-oxo-4-phenyl-2(5H)-furanylidene)-, methyl ester, (E)- |
| IUPAC Name | methyl (E)-2-(3-methoxy-5-oxo-4-phenylfuran-2(5H)-ylidene)-2-(2-methoxyphenyl)acetate |
| Canonical SMILES | COC1=CC=CC=C1C(=C2C(=C(C(=O)O2)C3=CC=CC=C3)OC)C(=O)OC |
| InChI | InChI=1S/C21H18O6/c1-24-15-12-8-7-11-14(15)17(20(22)26-3)19-18(25-2)16(21(23)27-19)13-9-5-4-6-10-13/h4-12H,1-3H3/b19-17+ |
| InChI Key | WGZKMINRLLRJPF-HTXNQAPBSA-N |
Properties
| Boiling Point | 618.3±55.0°C (Predicted) |
| Density | 1.29±0.1 g/cm3 (Predicted) |
Reference Reading
1. Design and Synthesis of Novel Oleanolic Acid-Linked Disulfide, Thioether, or Selenium Ether Moieties as Potent Cytotoxic Agents
Ya-Mei Li, Yu Zhang, Tian Luan, Chuan-Feng Liu Chem Biodivers. 2022 Apr;19(4):e202100831. doi: 10.1002/cbdv.202100831. Epub 2022 Feb 28.
A series of novel oleanolic acid (OA)-linked disulfide, thioether, or selenium ether derivatives was synthesized, and their antiproliferative activity was evaluated against human liver cancer (BEL-7402 and HepG-2), colon cancer (HCT116), and normal liver (L02) cell lines using methyl thiazolyl tetrazolium assay (MTT). Preliminary bioassay results revealed that OA derivatives modified at the C3-OH position, i. e., compound a4 containing sulfide ether, exhibited the best antiproliferative activity against BEL-7402 cells, with an IC50 value of 5.70±0.82 μM. Further flow cytometry assays revealed that compound a4 exerted its antiproliferative effects by inducing cell cycle arrest in the G2/M phase leading to apoptosis. Moreover, compared with the lead compound OA and the positive control drug 5-fluorouracil (5-FU), the OA derivatives demonstrated potent antiproliferative activities against the cancer cell lines.
2. ICl-Mediated Functional Group Interconversion from Methyl Homopropargyl Ether to α-Iodo-γ-chloroketone
Yu Chen, Samual Hee, Xiaochen Liu, Sajal Das, Dongsub Hong, Pak-Hing Leung, Yongxin Li, Jiaming Li, Jianbo Liu J Org Chem. 2022 Nov 18;87(22):15129-15138. doi: 10.1021/acs.joc.2c01638. Epub 2022 Nov 4.
An ICl-mediated highly chemo- and regioselective functional group interconversion from methyl homopropargyl ether to α-iodo-γ-chloro-ketone is reported. Density functional theory (DFT)-calculated reaction coordinate and potential energy surface support the high chemo-selectivity observed for the formation of α-iodo-γ-chloroketone over furan. The five-membered oxonium ring formation-ring opening mechanism is a potential template for the preparation of polyfunctionalized carbonyl compounds.
3. Methyl ester and aromatic ether modification of mitragynine for generation of mitragynine-specific polyclonal antibodies
Radhiahtul Raehan Mustafa, Rashidah Sukor, Siti Mariam Mohd Nor, Nazamid Saari J Immunol Methods. 2022 Aug;507:113291. doi: 10.1016/j.jim.2022.113291. Epub 2022 May 28.
Mitragynine is an alkaloid from Mitragyna speciosa Korth. (kratom), a native tropical plant in Southeast Asia. It could render psychotropic effects and is often misused in substitution for commercial drugs. In recent years, the consumption of kratom has grown rapidly and has led some countries to ban its use. The misuse of kratom can be detected and monitored through the determination of mitragynine from biological samples of the users. Therefore, the development of a rapid and effective detection method is needed. In this study, polyclonal antibodies were produced using mitragynine coupled to a carrier protein (cationic bovine serum albumin, cBSA) as an immunogen, which was prepared with coupling agents (i.e., N, N- dicyclohexylcarbodiimide, DCC and N-hydroxysuccinimide, NHS). It was conjugated to different mitragynine structure, 16-COOCH3 (methyl ester) and 9-OCH3 (aromatic ether). 2,4,6-Trinitrobenzenesulfonic acid (TNBS) method showed that 45 and 46 amino groups were bound to C22-MG-cBSA and C9-MG-cBSA, respectively. Fourier-transform infrared spectroscopy (FTIR) spectral changes at C22- and C9-hydroxymitragynine indicated reduction and demethylation process. In UV-Vis spectra, conjugated mitragynine to cBSA and OVA were displayed at a spectral region at 240-300 nm. For the antibody titre, the C22-MG-cBSA anti-serum showed a significantly higher titre than the C9-MG-cBSA at 1/128000 and 1/32000 dilutions, respectively. The detection range of the developed competitive indirect ELISA (CI-ELISA) was 0.01 to 10.00 μg/mL (R2 = 0.9964). The assay exhibited a limit of detection (LOD) and limit of quantification (LOQ) at 0.041 and 0.124 μg/mL, respectively. The antibody produced is a high-value biorecognition molecule that can be further used in developing immuno-based detection methods such as immunosensors and immunochromatographic lateral flow assays. This will benefit the task force or forensic agencies for toxicological screening with high speed and efficiency.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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