Methyl linolenate
(Synonyms: 亚麻酸甲酯; Linolenic acid methyl ester) 目录号 : GC36592
A methylated form of α-linolenic acid
Cas No.:301-00-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
α-Linolenic acid methyl ester is a natural methylated form of α-linolenic acid .1,2 Unlike α-linolenic acid, linolenic acid methyl ester is a poor agonist of GPR120, does not inhibit voltage-dependent calcium channels in β-cells, and only weakly inhibits melanogenesis in mouse B16 melanoma cells.3,4,5
1.Go, J.V., Rezanka, T., Srebnik, M., et al.Variability of fatty acid components of murine and freshwater gastropod speices from the littoral zone of the Red Sea, Mediterranean Sea, and Sea of GalileeBiochem. Syst. Ecol.30819-835(2002) 2.Mohadjerani, M., Hosseinzadeh, R., and Hosseini, M.Chemical composition and antibacterial properties of essential oil and fatty acids of different parts of Ligularia persica BoissAvicenna J. Phytomed.6(3)357-365(2016) 3.Sun, Q., Hirasawa, A., Hara, T., et al.Structure-activity relationships of GPR120 agonists based on a docking simulationMol. Pharm.78804-810(2010) 4.Feng, D.-D., Zhao, Y.-F., Luo, Z.-Q., et al.Linoleic acid induces Ca2+-induced inactivation of voltage-dependent Ca2+ currents in rat pancreatic β-cellsJ. Endocrinol.196(2)377-384(2008) 5.Huh, S., Kim, Y.-S., Jung, E., et al.Melanogenesis inhibitory effect of fatty acid alkyl esters isolated from Oxalis triangularisBiol. Pharm. Bull.33(7)1242-1245(2010)
| Cas No. | 301-00-8 | SDF | |
| 别名 | 亚麻酸甲酯; Linolenic acid methyl ester | ||
| Canonical SMILES | CC/C=C\C/C=C\C/C=C\CCCCCCCC(OC)=O | ||
| 分子式 | C19H32O2 | 分子量 | 292.46 |
| 溶解度 | DMSO: 50 mg/mL (170.96 mM); Water: < 0.1 mg/mL (insoluble) | 储存条件 | Store at -20°C, protect from light, stored under nitrogen |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.4193 mL | 17.0964 mL | 34.1927 mL |
| 5 mM | 0.6839 mL | 3.4193 mL | 6.8385 mL |
| 10 mM | 0.3419 mL | 1.7096 mL | 3.4193 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Autoxidation and yellowing of Methyl linolenate
Prog Lipid Res 1992;31(2):109-26.PMID:1461916DOI:10.1016/0163-7827(92)90005-4.
The autoxidation of fatty esters of linseed oil is studied extensively, and the products formed from these reactions are identified. The mechanism suggested for autoxidation, helps to understand fat deterioration resulting in offensive odours and flavours, and to develop new antioxidants to prevent this decomposition. The oxidation following oxidative copolymerization should be investigated in order to understand and to develop new methodology to prevent yellowing. Although the yellowing of indoor oil paints could be prevented to an extent, no compound is known to completely inhibit this process nor has the cause for this yellow colouration been isolated, leaving the doors wide open for further investigation.
Sageretia thea fruit extracts rich in methyl linoleate and Methyl linolenate downregulate melanogenesis via the Akt/GSK3β signaling pathway
Nutr Res Pract 2018 Feb;12(1):3-12.PMID:29399291DOI:10.4162/nrp.2018.12.1.3.
Background/objectives: Sageretia thea is traditionally used as a medicinal herb to treat various diseases, including skin disorders, in China and Korea. This study evaluated the inhibitory effect of Sageretia thea fruit on melanogenesis and its underlying mechanisms in B16F10 mouse melanoma cells. The active chemical compounds in anti-melanogenesis were determined in Sageretia thea. Materials/methods: Solvent fractions from the crude extract were investigated for anti-melanogenic activities. These activities and the mechanism of anti-melanogenesis in B16F10 cells were examined by determining melanin content and tyrosinase activity, and by performing western blotting. Results: The n-hexane fraction of Sageretia thea fruit (HFSF) exhibited significant anti-melanogenic activity among the various solvent fractions without reducing viability of B16F10 cells. The HFSF suppressed the expression of tyrosinase and tyrosinase-related protein 1 (TRP1). The reduction of microphthalmia-associated transcription factor (MITF) expression by the HFSF was mediated by the Akt/glycogen synthase kinase 3 beta (GSK3β) signaling pathway, which promotes the reduction of β-catenin. Treatment with the GSK3β inhibitor 6-bromoindirubin-3'-oxime (BIO) restored HFSF-induced inhibition of MITF expression. The HFSF bioactive constituents responsible for anti-melanogenic activity were identified by bioassay-guided fractionation and gas chromatography-mass spectrometry analysis as methyl linoleate and Methyl linolenate. Conclusions: These results indicate that HFSF and its constituents, methyl linoleate and Methyl linolenate, could be used as whitening agents in cosmetics and have potential for treating hyperpigmentation disorders in the clinic.
Benchmark Calculations for Bond Dissociation Enthalpies of Unsaturated Methyl Esters and the Bond Dissociation Enthalpies of Methyl linolenate
J Phys Chem A 2016 Jun 16;120(23):4025-36.PMID:27191950DOI:10.1021/acs.jpca.6b02600.
It is important to determine an appropriate computational method for obtaining accurate thermochemical properties of large biodiesel molecules such as Methyl linolenate. In this study, we use Kohn-Sham density functional theory (DFT) and coupled cluster theory to calculate bond dissociation enthalpies (BDEs) of seven fragment molecules of Methyl linolenate, in particular, propene, methyl formate, cis-3-hexene, 1,4-pentadiene, 1-pentene, butane, and methyl butanoate. The results are compared to BDEs obtained from experiments and to Oyeyemi et al.'s multireference averaged coupled pair functional (MRACPF2) calculations. We found that with extrapolation to the complete basis set (CBS) limit, the BDEs derived from coupled cluster calculations with single, double, and triple excitations (CCSDT) and from CCSDT with a perturbative treatment of connected quadruple excitations, CCSDT(2)Q/CBS, are closer to the available experimental values than those obtained by MRACPF2 for propene and methyl formate. The CCSDT/CBS calculations were chosen as the reference for validating the DFT methods. Among the density functionals, we found that M08-HX has the best performance with a mean unsigned deviation (MUD) from CCSDT/CBS of only 1.0 kcal/mol, whereas the much more expensive MRACPF2 has an MUD of 1.1 kcal/mol. We then used the most successfully validated density functionals to calculate the BDEs of Methyl linolenate and compared the results with the MRACPF2 BDEs. The present study identifies several Kohn-Sham exchange-correlation functionals that should be useful for modeling ester combustion, especially the M08-HX, M06-2X, M05-2X, M08-SO, and MPWB1K global-hybrid meta functionals, the M11 and MN12-SX range-separated-hybrid meta functionals, the ωB97 range-separated hybrid gradient approximation functional, and the SOGGA11-X global-hybrid gradient approximation functional.
NMR and Computational Studies as Analytical and High-Resolution Structural Tool for Complex Hydroperoxides and Diastereomeric Endo-Hydroperoxides of Fatty Acids in Solution-Exemplified by Methyl linolenate
Molecules 2020 Oct 23;25(21):4902.PMID:33113947DOI:10.3390/molecules25214902.
A combination of selective 1D Total Correlation Spectroscopy (TOCSY) and 1H-13C Heteronuclear Multiple Bond Correlation (HMBC) NMR techniques has been employed for the identification of Methyl linolenate primary oxidation products without the need for laborious isolation of the individual compounds. Complex hydroperoxides and diastereomeric endo-hydroperoxides were identified and quantified. Strongly deshielded C-O-O-H 1H-NMR resonances of diastereomeric endo-hydroperoxides in the region of 8.8 to 9.6 ppm were shown to be due to intramolecular hydrogen bonding interactions of the hydroperoxide proton with an oxygen atom of the five-member endo-peroxide ring. These strongly deshielded resonances were utilized as a new method to derive, for the first time, three-dimensional structures with an assignment of pairs of diastereomers in solution with the combined use of 1H-NMR chemical shifts, Density Functional Theory (DFT), and Our N-layered Integrated molecular Orbital and molecular Mechanics (ONIOM) calculations.
Comparative methyl linoleate and Methyl linolenate oxidation in the presence of bovine serum albumin at several lipid/protein ratios
J Agric Food Chem 2003 Jul 30;51(16):4661-7.PMID:14705893DOI:10.1021/jf025918j.
The oxidation of methyl linoleate (LMe) and Methyl linolenate (LnMe) in the presence of bovine serum albumin (BSA) in the dark at 60 degrees C was studied to analyze the role of the type of fatty acid and the protein/lipid ratio on the relative progression of the processes involved when lipid oxidation occurs in the presence of proteins. The disappearance of the fatty acid, the formation of primary and secondary products of lipid peroxidation, the loss of amino acid residues, the production of oxidized lipid/amino acid reaction products, and the development of color and fluorescence were studied as a function of incubation time in protein/lipid samples at 10:1, 6:1, and 3:1 w/w ratios. The incubation of LMe and LnMe in the presence of BSA at 60 degrees C rapidly produced lipid peroxidation and protein damage. Although reaction rates were much faster for LnMe than for LMe, both fatty acids had similar behaviors, and LnMe seemed to be only slightly more reactive than LMe for BSA by producing a higher increase of protein pyrroles in the protein and the development of increased browning and fluorescence. The protein/lipid ratio also influenced the relative progress of the reactions implicated. Thus, a lower protein/lipid ratio increased sample oxidation and protein damage. This also produced an increased browning, in accordance with the mechanisms proposed for browning production by oxidized lipid/protein reactions. On the contrary, browning of extracted lipids increased at higher protein/lipid ratios. This opposite tendency allowed evaluation of the overall significance of the different browning processes implicated in the final colors observed, concluding that color changes observed in BSA/lipid samples were mostly a consequence of oxidized lipid/protein reactions.