| Size | Price | Stock | Qty |
|---|---|---|---|
| 5g |
|
||
| Other Sizes |
| Targets |
Methyl linoleate targets the melanogenesis pathway. It downregulates microphthalmia-associated transcription factor (MITF) and tyrosinase-related proteins. By inhibiting these key regulators of melanin synthesis, it reduces melanin production. The compound also inhibits β-catenin-mediated signaling. Its antioxidant properties are related to its role as a lipid peroxidation substrate.
|
|---|---|
| ln Vitro |
Melanin synthesis is downregulated by sageretia thea fruit extract high in methyl linoleate via the Akt/GSK3β signaling pathway. By blocking the Akt/GSK3β signaling pathway, HFSF and methyl linoleate prevent β-catenin-mediated transcriptional activation of MITF [1].
In vitro, methyl linoleate downregulates microphthalmia-associated transcription factor (MITF) and tyrosinase-related proteins. It inhibits β-catenin-mediated signaling. The compound is used as a model compound in oxidation/peroxidation assays to evaluate the anti-peroxidation activity of fullerenes, ellagitannins, and other natural products. Its anti-melanogenic activity has been demonstrated in cell-based assays. |
| ln Vivo |
In vivo, methyl linoleate has been studied for its anti-melanogenic effects. As the main active component of Sageretia thea fruit (HFSF), it contributes to the fruit's skin-whitening properties. Its antioxidant properties suggest potential applications in preventing oxidative damage. Further in vivo studies are needed to evaluate its therapeutic potential.
|
| Enzyme Assay |
In vitro anti-melanogenic assays for methyl linoleate are performed using melanocytes or melanoma cells. Cells are treated with methyl linoleate at various concentrations. Melanin content is measured spectrophotometrically. Tyrosinase activity is assessed by measuring the oxidation of L-DOPA. MITF and tyrosinase-related protein levels are measured by Western blot or qRT-PCR.
|
| Cell Assay |
In vitro cellular studies are conducted using melanocytes or B16 melanoma cells. Cells are treated with methyl linoleate at various concentrations. Cell viability is assessed using MTT assays. Melanin content is measured. Tyrosinase activity is assessed. MITF and tyrosinase-related protein expression is analyzed by Western blot or qRT-PCR. The compound's effects on β-catenin signaling are also evaluated.
|
| Animal Protocol |
In vivo animal experiments with methyl linoleate are limited. The compound is a natural product with potential applications in skin whitening and antioxidant therapy. Further in vivo studies are needed to evaluate its efficacy. Animals would be administered methyl linoleate via topical application or oral gavage, and endpoints would include skin pigmentation assessment and oxidative stress marker measurement.
|
| ADME/Pharmacokinetics |
Methyl linoleate has a molecular formula of C19H34O2 and a molecular weight of 294.47 g/mol. It is a fatty acid methyl ester. It is soluble in organic solvents. For storage, it should be kept at -20°C, protected from light and moisture. The compound is supplied with high purity (≥99%). It is a standard analytical compound and is used as a model compound in oxidation assays.
|
| Toxicity/Toxicokinetics |
As a research chemical, methyl linoleate is not intended for human use. Its toxicological profile is not fully characterized. Standard laboratory safety precautions should be followed when handling it. Its effects are related to its mechanism as an anti-melanogenic compound and its role as a lipid peroxidation substrate.
|
| References | |
| Additional Infomation |
Methyl linoleate is a fatty acid methyl ester of linoleic acid. It has been isolated from Neolitsea daibuensis. It is a plant metabolite functionally related to linoleic acid. Methyl linoleate has also been reported to exist in Pourthiaea arguta, Eleutherococcus koreanus, and several other organisms with relevant data.
Methyl linoleate is also known as methyl (9Z,12Z)-octadeca-9,12-dienoate. It is a major active constituent of Sageretia thea fruit (HFSF) and is a major anti-melanogenic compound. It downregulates microphthalmia-associated transcription factor (MITF) and tyrosinase-related proteins. It is used in research on melanogenesis, skin pigmentation, and oxidative stress. |
| Molecular Formula |
C19H34O2
|
|---|---|
| Molecular Weight |
294.4721
|
| Exact Mass |
294.255
|
| CAS # |
112-63-0
|
| Related CAS # |
Linoleic Acid-d11 methyl ester
|
| PubChem CID |
5284421
|
| Appearance |
Colorless to light yellow liquid
|
| Density |
0.9±0.1 g/cm3
|
| Boiling Point |
373.3±21.0 °C at 760 mmHg
|
| Melting Point |
-35ºC(lit.)
|
| Flash Point |
96.9±20.4 °C
|
| Vapour Pressure |
0.0±0.8 mmHg at 25°C
|
| Index of Refraction |
1.465
|
| LogP |
7.64
|
| Hydrogen Bond Donor Count |
0
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
15
|
| Heavy Atom Count |
21
|
| Complexity |
279
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O(C([H])([H])[H])C(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C(/[H])=C(/[H])\C([H])([H])/C(/[H])=C(/[H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])=O
|
| InChi Key |
WTTJVINHCBCLGX-NQLNTKRDSA-N
|
| InChi Code |
InChI=1S/C19H34O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21-2/h7-8,10-11H,3-6,9,12-18H2,1-2H3/b8-7-,11-10-
|
| Chemical Name |
methyl (9Z,12Z)-octadeca-9,12-dienoate
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: 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)
|
| Solubility (In Vitro) |
DMSO : ~83.33 mg/mL (~282.98 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 6.25 mg/mL (21.22 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 62.5 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: 6.25 mg/mL (21.22 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 62.5 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: ≥ 6.25 mg/mL (21.22 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 | 3.3959 mL | 16.9797 mL | 33.9593 mL | |
| 5 mM | 0.6792 mL | 3.3959 mL | 6.7919 mL | |
| 10 mM | 0.3396 mL | 1.6980 mL | 3.3959 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
