Pinolenic Acid is a polyunsaturated fatty acid found in the seed oil of red pine (Pinus orientalis) and maritime pine (Pinus pinaster). Both oils were found to have lipid-lowering properties. A diet containing marine pine seed oil (MPSO) reduced high-density lipoprotein and ApoA1 levels in transgenic mice expressing human ApoA1. MPSO was found to reduce cholesterol efflux in vitro. Red pine seed oil supplements may help with obesity by reducing appetite. People who take this oil increase the satiety hormones CCK and GLP-1 and reduce appetite. The activity of the oil is attributed to terpineic acid. Pinolenic acid is not metabolically converted to arachidonic acid and can reduce arachidonic acid levels in the phosphatidylinositol fraction of HepG2 cells from 15.9% to 7.0%. Pinolenic acid ethyl ester is a neutral, more lipophilic form of the free acid.

Physicochemical Properties

Molecular Formula	C20H34O2
Molecular Weight	306.48
Exact Mass	306.255
CAS #	493015-74-0
PubChem CID	35027734
Appearance	Colorless to light yellow liquid（Density：0.893±0.06 g/cm3）
Density	0.9±0.1 g/cm3
Boiling Point	390.6±31.0 °C at 760 mmHg
Flash Point	100.8±23.2 °C
Vapour Pressure	0.0±0.9 mmHg at 25°C
Index of Refraction	1.475
LogP	7.65
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	15
Heavy Atom Count	22
Complexity	327
Defined Atom Stereocenter Count	0
SMILES	CCCCC/C=C\C/C=C\CC/C=C\CCCC(=O)OCC
InChi Key	VNRWOSFYACMRHX-UCVSHGSNSA-N
InChi Code	InChI=1S/C20H34O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22-4-2/h8-9,11-12,15-16H,3-7,10,13-14,17-19H2,1-2H3/b9-8-,12-11-,16-15-
Chemical Name	ethyl (5Z,9Z,12Z)-octadeca-5,9,12-trienoate
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: This product requires protection from light (avoid light exposure) during transportation and storage.
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

Additional Infomation

Pinolenic Acid ethyl ester is a lipid.

Solubility Data

Solubility (In Vitro)

DMSO: 100 mg/mL (326.29 mM)

Solubility (In Vivo)

Solubility in Formulation 1: 2.5 mg/mL (8.16 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication. 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 (8.16 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 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (8.16 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 25.0 mg/mL clear DMSO stock solution to 900 μL of 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	3.2629 mL	16.3143 mL	32.6286 mL
	5 mM	0.6526 mL	3.2629 mL	6.5257 mL
	10 mM	0.3263 mL	1.6314 mL	3.2629 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.