Methyl linoleate, the main active component of Sageretia thea fruit (HFSF), is a major anti-melanogenic compound. Methyl linoleate down-regulates microphthalmia-related transcription factor (MITF) and tyrosinase-related proteins.

Physicochemical Properties

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)

Biological Activity

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].
References	[1]. 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.
Additional Infomation	Methyl linoleate is a fatty acid methyl ester of linoleic acid. It has been isolated from Neolitsea daibuensis. It has a role as a plant metabolite. It is functionally related to a linoleic acid. Methyl linoleate has been reported in Pourthiaea arguta, Eleutherococcus koreanus, and other organisms with data available.

Solubility Data

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. 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. 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 corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

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.