EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

punicic acid
trichosanic acid

Supplier Sponsors

CAS Number: 544-72-9Picture of molecule3D/inchi
FDA UNII: VFQ03H211O
Nikkaji Web:J13.207A
XlogP3:6.40 (est)
Molecular Weight:278.43550000
Formula:C18 H30 O2
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
 water, 0.02371 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
9(Z),11(E),13(Z)-OCTADECATRIENOIC ACID
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5281126
National Institute of Allergy and Infectious Diseases:Data
(9Z,11E,13Z)-octadeca-9,11,13-trienoic acid
Chemidplus:0000544729
 
References:
 (9Z,11E,13Z)-octadeca-9,11,13-trienoic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5281126
Pubchem (cas):544-72-9
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
KEGG (GenomeNet):C08364
HMDB (The Human Metabolome Database):Search
FooDB:FDB002945
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 punica granatum seed
Search Trop Picture
 
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
 

Articles:

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 granatumL.) Seed Oil and Evaluation 
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 ¹⁸F-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.
 
Notes:
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