| Size | Price | Stock | Qty |
|---|---|---|---|
| 500mg |
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| 1g |
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| 5g |
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| Other Sizes |
| Targets |
Akt; GSK3β [4]
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|---|---|
| ln Vitro |
Methyl linolenate showed dose-dependent melanogenesis inhibitory activity in B16 murine melanoma cells. At concentrations of 10, 20, and 40 μM, it reduced melanin content by 23%, 41%, and 65% respectively compared to the vehicle control, with no significant cytotoxicity observed at these concentrations [1][3]
It inhibited tyrosinase (a key melanogenic enzyme) activity in B16 cells in a dose-dependent manner, achieving 30% inhibition at 40 μM [1][3] In B16F10 melanoma cells, Methyl linolenate (10–40 μM) downregulated the phosphorylation of Akt and GSK3β (detected by Western blot). This led to decreased expression of microphthalmia-associated transcription factor (MITF) and downstream melanogenic enzymes (tyrosinase, TRP-1, TRP-2), thereby suppressing melanin synthesis [4] |
| Cell Assay |
B16 cells were seeded in culture plates and incubated until reaching 70% confluence. The cells were treated with Methyl linolenate at final concentrations of 10, 20, and 40 μM, with vehicle as the control. After 72 hours of incubation, cells were dissolved in NaOH solution, and melanin content was quantified by measuring absorbance at 405 nm. For tyrosinase activity assay, cell lysates were mixed with L-DOPA substrate, and absorbance at 475 nm was recorded to assess enzyme activity [1][3]
B16F10 cells were cultured to 80% confluence and treated with Methyl linolenate (10, 20, 40 μM) for 48 hours. Cells were lysed to extract proteins, which were subjected to Western blot analysis to detect phosphorylated Akt (p-Akt), phosphorylated GSK3β (p-GSK3β), MITF, tyrosinase, TRP-1, and TRP-2. Cell viability was evaluated by MTT assay to rule out cytotoxic interference [4] |
| References |
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| Additional Infomation |
Methyl linolenate is a fatty acid methyl ester derived from α-linolenic acid. It is both a plant metabolite and an insect attractant. Its function is related to α-linolenic acid. Methyl linolenate has been reported to exist in Mikania goyazensis, Anchietea salutaris, and other organisms with relevant data. Methyl linolenate is a fatty acid alkyl ester isolated from Oxalis triangularis [1][3]. It is a key active ingredient in the fruit extract of Sageretia thea, which helps the extract inhibit melanin production [4]. Its mechanism of inhibiting melanin production involves regulating the Akt/GSK3β signaling pathway, thereby downregulating the expression of MITF and related melanin-producing enzymes [4].
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| Molecular Formula |
C19H32O2
|
|---|---|
| Molecular Weight |
292.48
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| Exact Mass |
292.24
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| CAS # |
301-00-8
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| Related CAS # |
Methyl linolenate-13C18
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| PubChem CID |
5319706
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| Appearance |
Colorless to light yellow liquid
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| Density |
0.9±0.1 g/cm3
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| Boiling Point |
364.4±0.0 °C at 760 mmHg
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| Melting Point |
-57℃
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| Flash Point |
101.4±20.4 °C
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| Vapour Pressure |
0.0±0.8 mmHg at 25°C
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| Index of Refraction |
1.476
|
| LogP |
6.96
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
14
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| Heavy Atom Count |
21
|
| Complexity |
314
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
CC/C=C\C/C=C\C/C=C\CCCCCCCC(OC)=O
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| InChi Key |
DVWSXZIHSUZZKJ-YSTUJMKBSA-N
|
| InChi Code |
InChI=1S/C19H32O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21-2/h4-5,7-8,10-11H,3,6,9,12-18H2,1-2H3/b5-4-,8-7-,11-10-
|
| Chemical Name |
methyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~341.93 mM)
H2O : < 0.1 mg/mL |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.55 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.55 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (8.55 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.4190 mL | 17.0952 mL | 34.1904 mL | |
| 5 mM | 0.6838 mL | 3.4190 mL | 6.8381 mL | |
| 10 mM | 0.3419 mL | 1.7095 mL | 3.4190 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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