punicic acid
trichosanic acid
Identification
| Name | punicic acid |
| CAS Number | 544-72-9 |
| FDA UNII | VFQ03H211O |
| Molecular Formula | C18 H30 O2 |
| Molecular Weight | 278.43550000 |
| Nikkaji Number | J13.207A |
| XlogP3 | 6.40 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 0.02371 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for punicic acid usage levels up to | not for fragrance use. |
| Recommendation for punicic acid flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
(9Z,11E,13Z)-
octadeca-9,11,13-trienoic acid
9Z,11E,13Z-
octadeca-9,11,13-trienoic acid
9-cis,11-trans,13-cis-
octadecatrienoic acid
punicinic acid
trichosanic acid
trichosanoic acid
PubMed:
Bioactivity and biotechnological production of punicic acid.
PubMed:
Quality of pomegranate pomace as affected by drying method.
PubMed:
Insulin resistance in 3T3-L1 adipocytes by TNF-α is improved by punicic acid through upregulation of insulin signalling pathway and endocrine function, and downregulation of proinflammatory cytokines.
PubMed:
Stimulation of liver IGF-1 expression promotes peak bone mass achievement in growing rats: a study with pomegranate seed oil.
PubMed:
Metabolic engineering of Schizosaccharomyces pombe to produce punicic acid, a conjugated fatty acid with nutraceutic properties.
PubMed:
Phytochemical content, Fatty acids composition and antioxidant potential of different pomegranate parts: Comparison between edible and non edible varieties grown in Tunisia.
PubMed:
Optimisation of Microwave-Assisted Extraction of Pomegranate (
Punica granatum
L.) Seed Oil and Evaluation â¨of Its Physicochemical and Bioactive Properties.
PubMed:
Pomegranate seed oil influences the fatty acids profile and reduces the activity of desaturases in livers of Sprague-Dawley rats.
PubMed:
Punicic acid: A striking health substance to combat metabolic syndromes in humans.
PubMed:
Pomegranate as a possible treatment in reducing risk of developing wound healing, obesity, neurodegenerative disorders, and diabetes mellitus.
PubMed:
The linin promoter is highly effective in enhancing punicic acid production in Arabidopsis.
PubMed:
Effect of dietary pomegranate seed oil on laying hen performance and physicochemical properties of eggs.
PubMed:
Oxidative Stability of Pomegranate (Punica granatum L.) Seed Oil to Simulated Gastric Conditions and Thermal Stress.
PubMed:
Influence of pomegranate seed oil and bitter melon aqueous extract on polyunsaturated fatty acids and their lipoxygenase metabolites concentration in serum of rats.
PubMed:
The Effect of Xanthigen on the Expression of Brown Adipose Tissue Assessed by ¹â¸F-FDG PET.
PubMed:
Incorporation and effects of punicic acid on muscle and adipose tissues of rats.
PubMed:
Modeling-Enabled Characterization of Novel NLRX1 Ligands.
PubMed:
Treatment of a multiple sclerosis animal model by a novel nanodrop formulation of a natural antioxidant.
PubMed:
New lipase assay using Pomegranate oil coating in microtiter plates.
PubMed:
Insulin resistance by TNF-α is associated with mitochondrial dysfunction in 3T3-L1 adipocytes and is ameliorated by punicic acid, a PPARγ agonist.
PubMed:
Modulation of peroxisome proliferator-activated receptor gamma (PPAR γ) by conjugated fatty acid in obesity and inflammatory bowel disease.
PubMed:
Pomegranate and its components as alternative treatment for prostate cancer.
PubMed:
Punica granatum cv. Dente di Cavallo seed ethanolic extract: antioxidant and antiproliferative activities.
PubMed:
An in vitro study reveals the nutraceutical potential of punicic acid relevant to diabetes via enhanced GLUT4 expression and adiponectin secretion.
PubMed:
Luteolin, ellagic acid and punicic acid are natural products that inhibit prostate cancer metastasis.
PubMed:
Combined transgenic expression of Punica granatum conjugase (FADX) and FAD2 desaturase in high linoleic acid Arabidopsis thaliana mutant leads to increased accumulation of punicic acid.
PubMed:
Potential anti-inflammatory effects of the hydrophilic fraction of pomegranate (Punica granatum L.) seed oil on breast cancer cell lines.
PubMed:
Conjugated linolenic acids and their bioactivities: a review.
PubMed:
Pomegranate seed oil nanoemulsions for the prevention and treatment of neurodegenerative diseases: the case of genetic CJD.
PubMed:
Effects of pomegranate seed oil on insulin release in rats with type 2 diabetes.
PubMed:
Pomegranate Seed Oil Modulates Functions and Survival of BV-2 Microglial Cells in vitro.
PubMed:
Enrichment of functional properties of ice cream with pomegranate by-products.
PubMed:
Pomegranate seed oil prevents bone loss in a mice model of osteoporosis, through osteoblastic stimulation, osteoclastic inhibition and decreased inflammatory status.
PubMed:
Preventive and prophylactic mechanisms of action of pomegranate bioactive constituents.
PubMed:
Pomegranate and type 2 diabetes.
PubMed:
Effects of pomegranate seed oil on glucose and lipid metabolism-related organs in rats fed an obesogenic diet.
PubMed:
Long chain fatty acids and gene expression in inflammation and immunity.
PubMed:
Nutritional protective mechanisms against gut inflammation.
PubMed:
Jacaric acid and its octadecatrienoic acid geoisomers induce apoptosis selectively in cancerous human prostate cells: a mechanistic and 3-D structure-activity study.
PubMed:
Protective effect of conjugated linolenic acid isomers present in vegetable oils against arsenite-induced renal toxicity in rat model.
PubMed:
Specific pomegranate juice components as potential inhibitors of prostate cancer metastasis.
PubMed:
Pomegranate juice and specific components inhibit cell and molecular processes critical for metastasis of breast cancer.
PubMed:
Synergistic effect of conjugated linolenic acid isomers against induced oxidative stress, inflammation and erythrocyte membrane disintegrity in rat model.
PubMed:
Optimization of ultrasonic-assisted extraction of pomegranate (Punica granatum L.) seed oil.
PubMed:
Pomegranate seed oil reduces intestinal damage in a rat model of necrotizing enterocolitis.
PubMed:
Antioxidant properties and phytochemical composition of China-grown pomegranate seeds.
PubMed:
Uptake of conjugated linolenic acids and conversion to cis-9, trans-11-or trans-9, trans-11-conjugated linoleic acids in Caco-2 cells.
PubMed:
Conjugated fatty acid synthesis: residues 111 and 115 influence product partitioning of Momordica charantia conjugase.
PubMed:
Xanthigen suppresses preadipocyte differentiation and adipogenesis through down-regulation of PPARγ and C/EBPs and modulation of SIRT-1, AMPK, and FoxO pathways.
PubMed:
Antioxidant and anti-inflammatory effect of conjugated linolenic acid isomers against streptozotocin-induced diabetes.
PubMed:
Effect of pomegranate seed oil on serum TNF-α level in dyslipidemic patients.
PubMed:
Comparative study of hypocholesterolemic and hypolipidemic effects of conjugated linolenic acid isomers against induced biochemical perturbations and aberration in erythrocyte membrane fluidity.
PubMed:
Short communication: effects of supplementation with pomegranate seed pulp on concentrations of conjugated linoleic acid and punicic acid in goat milk.
PubMed:
Activation of PPARγ and δ by dietary punicic acid ameliorates intestinal inflammation in mice.
PubMed:
Pomegranate seed oil, a rich source of punicic acid, prevents diet-induced obesity and insulin resistance in mice.
PubMed:
Antioxidant effect of vegetable oils containing conjugated linolenic acid isomers against induced tissue lipid peroxidation and inflammation in rat model.
PubMed:
Treatment of Obesity-Related Complications with Novel Classes of Naturally Occurring PPAR Agonists.
PubMed:
Recent advances in the analysis of the site-specific isotopic fractionation of metabolites such as fatty acids using anisotropic natural-abundance 2H NMR spectroscopy: application to conjugated linolenic methyl esters.
PubMed:
Growth inhibitory, antiandrogenic, and pro-apoptotic effects of punicic acid in LNCaP human prostate cancer cells.
PubMed:
Ameliorative role of conjugated linolenic acid isomers against oxidative DNA damage induced by sodium arsenite in rat model.
PubMed:
Effect of pomegranate seed oil on hyperlipidaemic subjects: a double-blind placebo-controlled clinical trial.
PubMed:
Pomegranate (Punica granatum) seed linolenic acid isomers: concentration-dependent modulation of estrogen receptor activity.
PubMed:
Punicic acid is an omega-5 fatty acid capable of inhibiting breast cancer proliferation.
PubMed:
Activation of PPAR gamma and alpha by punicic acid ameliorates glucose tolerance and suppresses obesity-related inflammation.
PubMed:
Incorporation and metabolism of punicic acid in healthy young humans.
PubMed:
Antioxidant capacity and lipid characterization of six Georgia-grown pomegranate cultivars.
PubMed:
Punicic acid a conjugated linolenic acid inhibits TNFalpha-induced neutrophil hyperactivation and protects from experimental colon inflammation in rats.
PubMed:
Comparative study of antioxidant activity of alpha-eleostearic acid and punicic acid against oxidative stress generated by sodium arsenite.
PubMed:
Punicic acid from Trichosanthes kirilowii seed oil is rapidly metabolized to conjugated linoleic acid in rats.
PubMed:
Pomegranate oil analysis with emphasis on MALDI-TOF/MS triacylglycerol fingerprinting.
PubMed:
Genetically modified rapeseed oil containing cis-9,trans-11,cis-13-octadecatrienoic acid affects body fat mass and lipid metabolism in mice.
PubMed:
Re-characterization of three conjugated linolenic acid isomers by GC-MS and NMR.
PubMed:
Conjugated linolenic acid is slowly absorbed in rat intestine, but quickly converted to conjugated linoleic acid.
PubMed:
Dietary effect of pomegranate seed oil on immune function and lipid metabolism in mice.
PubMed:
Pomegranate (Punica granatum) pure chemicals show possible synergistic inhibition of human PC-3 prostate cancer cell invasion across Matrigel.
PubMed:
Dietary effect of pomegranate seed oil rich in 9cis, 11trans, 13cis conjugated linolenic acid on lipid metabolism in obese, hyperlipidemic OLETF rats.
PubMed:
Delta 12-oleate desaturase-related enzymes associated with formation of conjugated trans-delta 11, cis-delta 13 double bonds.
PubMed:
Formation of conjugated Delta11Delta13-double bonds by Delta12-linoleic acid (1,4)-acyl-lipid-desaturase in pomegranate seeds.
PubMed:
Antioxidant and eicosanoid enzyme inhibition properties of pomegranate seed oil and fermented juice flavonoids.