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Punicic acid

CAT: 0804-HY-139066Size: 1 mg (35.92 mM x 100 μL in Methanol)Dry Ice: NoHazardous: No
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CAT#:0804-HY-139066Size:1 mg (35.92 mM x 100 μL in Methanol)
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
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].
CAS Number
544-72-9
Product Name Alternative
Trichosanic acid
UNSPSC
12352211
Hazard Statement
H302, H315, H319, H335
Target
GLUT; PKC; Proteasome; Tau Protein; TNF Receptor
Type
Natural Products
Related Pathways
Apoptosis; Epigenetics; Membrane Transporter/Ion Channel; Metabolic Enzyme/Protease; Neuronal Signaling; TGF-beta/Smad
Applications
Metabolism-sugar/lipid metabolism
Field of Research
Metabolic Disease; Inflammation/Immunology; Neurological Disease
Assay Protocol
https://www.medchemexpress.com/punicic-acid.html
Concentration
35.92 mM * 100 μL in Methanol
Purity
98.5
Solubility
DMSO : 100 mg/mL (ultrasonic; warming; heat to 60°C)
Smiles
CCCC/C=C\C=C\C=C/CCCCCCCC(O)=O
Molecular Formula
C18H30O2
Molecular Weight
278.43
Precautions
H302, H315, H319, H335
References & Citations
[1]Shabbir MA, et al. Punicic acid: A striking health substance to combat metabolic syndromes in humans. Lipids Health Dis. 2017;16 (1) :99.|[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.|[3]Guerra-Vázquez, et al. Punicic acid and its role in the prevention of neurological disorders: A review. Foods 11.3 (2022) : 252.|[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.
Shipping Conditions
Blue Ice
Storage Conditions
Solution, -20°C, 2 years
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Punicic Acid

(9Z,11E,13Z)-octadecatrienoic acid is 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). It has a role as an antineoplastic agent and a plant metabolite.

CAS Number544-72-9
PubChem CID5281126
IUPAC Name(9Z,11E,13Z)-octadeca-9,11,13-trienoic acid
Molecular FormulaC18H30O2
Molecular Weight278.4
XLogP6.4
Topological Polar Surface Area37.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count13
Heavy Atom Count20
Formal Charge0
Complexity301
SMILES
CCCC/C=C\C=C\C=C/CCCCCCCC(=O)O
InChI
InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h5-10H,2-4,11-17H2,1H3,(H,19,20)/b6-5-,8-7+,10-9-
InChIKey
CUXYLFPMQMFGPL-BGDVVUGTSA-N
Chemical Structure
2D Structure
2D structure of Punicic Acid
CAS: 544-72-9
CID: 5281126
Formula: C18H30O2
MW: 278.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight278.4
XLogP36.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count13
Exact Mass278.224580195
Monoisotopic Mass278.224580195
Topological Polar Surface Area37.3 Ų
Heavy Atom Count20
Formal Charge0
Complexity301
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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