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Cas No: 16833-54-8
Pinolenic acid (often misspelled as pinoleic acid) is a fatty acid contained in Siberian Pine nuts, Korean Pine nuts and the seeds of other pines (Pinus species).
The highest percentage of pinolenic acid is found in Siberian pine nuts and the oil produced from them.
Chemistry and biochemistry
Pinolenic acid is formally designated as all-cis-5,9,12-18:3.
Some sources also use the term columbinic acid for this substance.
But columbinic acid sometimes designates an E-Z isomer (trans,cis,cis delta-5,9,12/18:3) in the biologic literature.
Pinolenic acid is an isomer of gamma-linolenic acid (GLA). GLA is an ω-6 essential fatty acid (EFA) but pinolenic acid is not.
However, like the EFAs, it forms biologically active metabolites in the presence of cyclooxygenase or lipoxygenase.
These metabolites can partially relieve some of the symptoms of EFA deficiency.
Physiology
Recent research has shown its potential use in weight loss by curbing appetite.
Pinolenic acid causes the triggering of two hunger suppressants—cholecystokinin and glucagon-like peptide-1 (GLP-1).
Pinolenic acid may have LDL-lowering properties by enhancing hepatic LDL uptake.
Pinolenic acid is an octadecatrienoic acid having three double bonds located at positions 5, 9 and 12 (the all-cis-isomer).
It has a role as a plant metabolite and an antineoplastic agent.
Pinolenic acid is a natural product found in Teucrium cubense and Pinus koraiensis with data available.
Pinolenic Acid is found in pine nuts in commercial samples that results in pine nut syndrome.
Pinolenic acid is a polyunsaturated fatty acid found in Korean pine (Pinus orientalis) and maritime pine (Pinus pinaster) seed oils. Both oils have been found to have lipid-lowering properties.
A diet containing maritime pine seed oil (MPSO) lowered HDL and ApoA1 levels in transgenic mice expressing human ApoA1.
MPSO was found to diminish cholesterol efflux in vitro.1 Korean pine seed oil supplements may help in obesity by reduction of appetite.
People taking this oil had an increase in the satiety hormones CCK and GLP-1 and a reduced desire to eat.
The activity of the oil is attributed to pinolenic acid.
Pinolenic acid is not converted to arachidonic acid metabolically and can reduce arachidonic acid levels in the phosphatidylinositol fraction of HepG2 cells from 15.9% to 7.0%.
Formal Name: 5Z,9Z,12Z-octadecatrienoic acid
CAS Number: 16833-54-8
Molecular Formula: C18H30O2
Formula Weight: 278.4
Purity: ≥98%
Pinolenic acid (PLA) is a polyunsaturated fatty acid of plant origin.
PLA has been successfully enriched according to a two-step process involving lipase-catalysed esterification and urea complexation.
For the first step, the fatty acids present in pine nut oil were selectively esterified with lauryl alcohol using Candida rugosa lipase.
Under the optimum conditions of 0.1% enzyme loading, 10% additional water, and 15°C, PLA was enriched up to 43mol% from an initial value of 13mol% in the pine nut oil.
For the second step, the PLA-enriched fraction from the first step was subjected to a urea complexation process.
In this way, PLA enrichments with purities greater than 95mol% were obtained at urea to fatty acid ratios greater than 3:1 (wt/wt), and 100% pure PLA was produced at a urea to fatty acid ratio of 5:1 with an 8.7mol% yield.
Pinolenic acid, omega 6, extracted from pinus koraiensis nut oil, has function of lowering cholesterol, treating obesity and diabetes,etc.
Pinolenic Acid is a polyunsaturated fatty acid found in maritime pine (Pinus pinaster) and Korean pine (Pinus orientalis) seed oils, where both oils have lipid-lowering properties.
Pinolenic acid is an isomer of gamma-linolenic acid and forms biologically acitve metabolites in the presence of cyclooxygenase or lipoxygenase.
A diet containing maritime pine seed oil (MPSO) lowered HDL and ApoA1 levels in transgenic mice expressing human ApoA1.
MPSO was found to diminish cholesterol efflux in vitro.
Korean pine seed oil supplements may help in obesity by reduction of appetite.
The activity of the oil is attributed to pinolenic acid.
Pinolenic acid may have LDL-lowering properties by enhancing hepatic LDL uptake.
Pinolenic acid is a polyunsaturated fatty acid found in Korean pine (Pinus orientalis) and maritime pine (Pinus pinaster) seed oils.
Both oils have been found to have lipid-lowering properties.
A diet containing maritime pine seed oil (MPSO) lowered HDL and ApoA1 levels in transgenic mice expressing human ApoA1.
MPSO was found to diminish cholesterol efflux in vitro.
Korean pine seed oil supplements may help in obesity by reduction of appetite.
People taking this oil had an increase in the satiety hormones CCK and GLP-1 and a reduced desire to eat.
The activity of the oil is attributed to pinolenic acid.
Pinolenic acid is not converted to arachidonic acid metabolically and can reduce arachidonic acid levels in the phosphatidylinositol fraction of HepG2 cells from 15.9% to 7.0%.
Formal Name: 5Z,9Z,12Z-octadecatrienoic acid.
CAS Number: 16833-54-8.
Molecular Formula: C18H30O2.
Formula Weight: 278.4.
Purity: >98%.
Formulation: A solution in ethanol.
Solubility: DMF: 30 mg/ml,
DMSO: 30 mg/ml,
Ethanol: 100 mg/ml,
Ethanol:PBS (pH 7.2) (1:1): .5 mg/ml.
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
SYNONYMS:
HXQHFNIKBKZGRP-URPRIDOGSA-N
5,9,12-Octadecatrienoicacid, (5Z,9Z,12Z)-
Pinolenic Acid (pine nut oil), 40%
Pinolenic acid
16833-54-8
5Z,9Z,12Z-octadecatrienoic acid
UNII-B810C93MD7
(5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid
cis,cis,cis-5,9,12-Octadecatrienoic acid
C18:3n-6,9,13
B810C93MD7
Pinolenic acid [MI]
5,9,12-Octadecatrienoic acid, (5Z,9Z,12Z)-
SCHEMBL1021463
CHEBI:86136
DTXSID00895852
HMS3650G16
1990AH
LMFA01030344
ZINC27646178
(5Z,9Z,12Z)-octadecatrienoic acid
all-cis-octadeca-5,9,12-trienoic acid
(z,z,z)-5,9,12-octadecatrienoic acid
SR-01000946285
J-010448
SR-01000946285-1
Q63408763
