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Methyl punicate

Methyl 9(Z),11(E),13(Z)-Octadecatrienoate; Conjugated linolenic acid methyl ester; CLnA

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Punicic acid is a conjugated linolenic acid (CLnA) that is found in high amounts in several natural oils, including pomegranate and snake guard seed oils. CLnAs contain 3 or 4 double bonds (which can be any combination of cis or trans) and 9,11,13- and 8,10,12-octadecatrienoic acid positional isomers. Research indicates that CLnAs posses strong antidiabetic, antiobesity, antiproliferative, and anticarcinogenic activities as well as a significant affect on lipid metabolism.(1) These physiological effects make CLnAs potential candidates as therapeutic agents, although more research is needed to verify previous findings.(2) Some studies suggest that punicic acid and other CLnAs can reduce adipose tissue in mouse models, making it potentially useful as a weight-controlling lipid.(3) CLnAs, including punicic, jacaric, and α-eleostearic acids, have been shown to suppress tumor cell growth through lipoperoxidation and apoptotic pathways.(4,5) It has been found that some CLnAs, such as punicic acid and jacaric acid, exert a potent anti-inflammatory effect through the inhibition of TNFα-induced priming of ROS production and inhibition of cyclooxygenase 1 (COX-1).(6,7) Punicic acid also modulates mucosal immune responses and ameliorates gut inflammation through PPAR γ and δ-dependent mechanisms.(8) In addition, pomegranate oil has been demonstrated to inhibit estrogen receptors α and β, with both punicic acid and α-eleostearic acid being identified as active inhibitors.(9)

Cat#	Size	Price	Qty	Buy
1240	25 mg	£165.75

Additional Information

Property	Value or Rating
Product Size	25 mg
Manufacturer	Matreya, LLC
Empirical Formula	C19H32O2
CAS#	95497-55-5
Formula Weight	292.5
Solvent	none
Source	natural
Purity	97+%
Analytical Methods	GC; TLC; identity confirmed by MS
Natural Source	Plant
Solubility	hexane, ethanol, methanol, chloroform
Physical Appearance	A neat liquid
Storage	-20°C
References	1. P. Aruna et al. Health Benefits of Punicic Acid: A Review. Comprehensive Reviews in Food Science and Food Safety. Vol. 15 pp. 16-27, 2016 2. I. Pereira et al. Pomegranate Seed Oil (Punica Granatum L.): A Source of Punicic Acid (Conjugated α-Linolenic Acid). Journal of Human Nutrition and Food Science. Vol. 2(1) pp. 1024, 2014 3. Koba et al. Genetically Modified Rapeseed Oil Containing cis-9, trans-11, cis-13-Octadecatrienoic Acid Affects Body Fat Mass and Lipid Metabolism in Mice. J. Agric Food Chem. Vol. 55(9) pp. 3741-3748, 2007 4. T. Tsuzuki et al. Tumor growth suppression by α-eleostearic acid, a linolenic acid isomer with a conjugated triene system, via lipid peroxidation. Carcinogenesis. Vol. 25(8) pp. 1417-1425, 2004 5. J. Gasmi and J. Sanderson. Jacaric acid and its octadecatrienoic acid geoisomers induce apoptosis selectively in cancerous human prostate cells: a mechanistic and 3-D structure–activity study. Phytomedicine. Vol. 20 pp. 734-742, 2013 6. T. Boussetta et al. Punicic Acid a Conjugated Linolenic Acid Inhibits TNFα-Induced Neutrophil Hyperactivation and Protects from Experimental Colon Inflammation in Rats. PLoS One. Vol. 4(7) pp. e6468, 2009 7. Z. Mashhadi et al. Robust Inhibitory Effects of Conjugated Linolenic Acids on a Cyclooxygenase-related Linoleate 10S-Dioxygenase: Comparison with COX-1 and COX-2. Biochim. Biophys. Acta. Vol. 1851(10) pp. 1346-1352, 2015 8. J. Bassaganya-Riera et al. Punicic acid modulates mucosal immune responses and prevents gut inflammation through PPAR γ and δ-dependent mechanisms. FASEB. Vol. 24(1) pp. 926, 2010 9. H. Tran et al. Pomegranate (punica granatum) seed linolenic acid isomers: concentration-dependent modulation of estrogen receptor activity. Endocr. Res. Vol. 35(1) pp. 1-16, 2010

Related Documents

1. P. Aruna et al. Health Benefits of Punicic Acid: A Review. Comprehensive Reviews in Food Science and Food Safety. Vol. 15 pp. 16-27, 2016
2. I. Pereira et al. Pomegranate Seed Oil (Punica Granatum L.): A Source of Punicic Acid (Conjugated α-Linolenic Acid). Journal of Human Nutrition and Food Science. Vol. 2(1) pp. 1024, 2014
3. Koba et al. Genetically Modified Rapeseed Oil Containing cis-9, trans-11, cis-13-Octadecatrienoic Acid Affects Body Fat Mass and Lipid Metabolism in Mice. J. Agric Food Chem. Vol. 55(9) pp. 3741-3748, 2007
4. T. Tsuzuki et al. Tumor growth suppression by α-eleostearic acid, a linolenic acid isomer with a conjugated triene system, via lipid peroxidation. Carcinogenesis. Vol. 25(8) pp. 1417-1425, 2004
5. J. Gasmi and J. Sanderson. Jacaric acid and its octadecatrienoic acid geoisomers induce apoptosis selectively in cancerous human prostate cells: a mechanistic and 3-D structure–activity study. Phytomedicine. Vol. 20 pp. 734-742, 2013
6. T. Boussetta et al. Punicic Acid a Conjugated Linolenic Acid Inhibits TNFα-Induced Neutrophil Hyperactivation and Protects from Experimental Colon Inflammation in Rats. PLoS One. Vol. 4(7) pp. e6468, 2009
7. Z. Mashhadi et al. Robust Inhibitory Effects of Conjugated Linolenic Acids on a Cyclooxygenase-related Linoleate 10S-Dioxygenase: Comparison with COX-1 and COX-2. Biochim. Biophys. Acta. Vol. 1851(10) pp. 1346-1352, 2015
8. J. Bassaganya-Riera et al. Punicic acid modulates mucosal immune responses and prevents gut inflammation through PPAR γ and δ-dependent mechanisms. FASEB. Vol. 24(1) pp. 926, 2010
9. H. Tran et al. Pomegranate (punica granatum) seed linolenic acid isomers: concentration-dependent modulation of estrogen receptor activity. Endocr. Res. Vol. 35(1) pp. 1-16, 2010

Methyl punicate

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