| Identification | Back Directory | [Name]
Punicic acid | [CAS]
544-72-9 | [Synonyms]
punicicaci
PUNICIC ACID
Trichosanic acid
Trichosanic acid【C18】
9(Z),11(E),13(Z)-OCTADECATRIENOIC ACID
(9Z,11E,13Z)-9,11,13-Octadecatrienoic acid
(9Z,11E,13Z)-Octadeca-9,11,13-trienoic acid
9,11,13-Octadecatrienoic acid, (9Z,11E,13Z)- | [Molecular Formula]
C18H30O2 | [MDL Number]
MFCD05864026 | [MOL File]
544-72-9.mol | [Molecular Weight]
278.43 |
| Chemical Properties | Back Directory | [Melting point ]
62°C | [Boiling point ]
361.24°C (rough estimate) | [density ]
0.9027 | [refractive index ]
1.5114 | [solubility ]
DMF: 30 mg/mL; DMSO: 10 mg/mL; Ethanol: 20 mg/mL | [form ]
Liquid | [pka]
4.78±0.10(Predicted) | [color ]
Colorless to light yellow |
| Hazard Information | Back Directory | [Uses]
Punicic acid is a bioactive compound of pomegranate seed oil. Punicic acid is an isomer of conjugated α-linolenic acid and ω-5 polyunsaturated fatty acids. Punicic acid has anti-inflammatory and antioxidant activities and can inhibit the expression of inflammatory mediators such as tumor necrosis factor α (TNF-α). Punicic acid can also reduce the formation of β-amyloid deposits and hyperphosphorylation of tau by increasing the expression of GLUT4 protein and inhibiting the overactivation of calpain, and is used to prevent and treat neurodegenerative diseases. In addition, punicic acid also has breast cancer inhibitor properties that depend on lipid peroxidation and PKC pathways[1][2][3][4]. | [Definition]
ChEBI: A 9,11,13-octadecatrienoic acid having its double bonds in cis, trans and cis configurations, respectively. It has been isolated from pomegranate (Punica granatum). | [Synthesis]
[1] put 1000g of pomegranate seeds into the extractor for supercritical CO2 extraction, extraction pressure 25MPa, extraction temperature 45 ℃, separation pressure 9MPa, separation temperature 60 ℃, to get 140g of pomegranate seed oil; [2] the pomegranate | [in vivo]
Punicic acid (400 μg, i.g.; once daily for ten days) reduces significantly the TNBS-induced colonic damage in male Wistar rats by demonstrating mild inflammatory infiltration accompanied by punctate mucosal erosions[2]. | Animal Model: | TNBS-induced Colitis male Wistar rat[1] | | Dosage: | 400 μg | | Administration: | i.g. | | Result: | Reduced the hyperactivation of neutrophils in the colon of TNBS-treated rats and inhibited the release of MPO and ROS by neutrophils, thereby reducing lipid peroxidation and tissue damage. |
| [References]
[1] Shabbir MA, et al. Punicic acid: A striking health substance to combat metabolic syndromes in humans. Lipids Health Dis. 2017;16(1):99. DOI:10.1186/s12944-017-0489-3
[2] Boussetta T, et al. Punicic acid a conjugated linolenic acid inhibits TNFα-induced neutrophil hyperactivation and protects from experimental colon inflammation in rats[J]. PloS one, 2009, 4(7): e6458. DOI:10.1371/journal.pone.0006458
[3] Guerra-Vázquez, et al. Punicic acid and its role in the prevention of neurological disorders: A review. Foods 11.3 (2022): 252. DOI:10.3390/foods11030252
[4] Grossmann, et al. Punicic acid is an ω-5 fatty acid capable of inhibiting breast cancer proliferation. International journal of oncology 36.2 (2010): 421-426. PMID:20043077 |
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Alfa Chemistry
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