PRODUCTS

PUNICIC ACID

Punicic acid is a naturally occurring conjugated fatty acid predominantly found in pomegranate seed oil, obtained from the seeds of the Punica granatum.
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 is a conjugated linolenic acid or CLnA; i.e. it has three conjugated double bonds.

CAS Number: 65999-44-0
Molecular Formula: C18H30O2
Molecular Weight: 278.43 g/mol

Synonyms: Trichosanic acid, 544-72-9, Trichosanoic acid, 9-cis,11-trans,13-cis-octadecatrienoic acid, cis-9,trans-11,cis-13-Octadecatrienoic acid, VFQ03H211O, 9,11,13-Octadecatrienoic acid, (9Z,11E,13Z)-, 9,11,13-Octadecatrienoic acid, (Z,Z,E)-, 9Z,11E,13Z-octadecatrienoic acid, cis,trans,cis-9,11,13-Octadecatrienoic acid, 9Z,11E,13Z-octadeca-9,11,13-trienoic acid, CHEBI:8638, DTXSID10897463, RefChem:46672, Fatty Acid 18:3 n-5, DTXCID801326803, Cis,trans,cis-octadeca-9,11,13-trienoic acid, (9Z,11E,13Z)-octadeca-9,11,13-trienoic acid, 9(Z),11(E),13(Z)-OCTADECATRIENOIC ACID, (9Z,11E,13Z)-octadecatrienoic acid, cis-9, trans-11, cis-13-octadecatrienoic acid, Punicinic acid, 9c,11t,13c-linolenic acid, octadeca-9c,11t,13c-trienoic acid, 9c,11t,13c-18:3, C18:3 n-5 cis, 7 trans, 9 cis, 9cis,11trans,13cis-octadecatrienoic acid, (Z,E,Z)-octadeca-9,11,13-trienoic acid, UNII-VFQ03H211O, SCHEMBL158967, orb2278597, CHEMBL5205249, Octadeca-9c,11t,13c-triensaeure, LMFA01030146, MFCD05864026, MSK169513, PD088520, HY-139066, CS-0179308, C08364, Q201502, 9(Z) pound not11(E) pound not13(Z)-Octadecatrienoic Acid

Punicic acid is a naturally occurring conjugated fatty acid predominantly found in pomegranate seed oil, obtained from the seeds of the Punica granatum.
Punicic acid is chemically classified as a conjugated linolenic acid (CLnA) and is known for its unique structure containing conjugated double bonds, which contribute to its strong antioxidant and biological activity.
Punicic acid is widely studied in food science, nutraceuticals, and cosmetic applications due to its potential health-promoting properties, including anti-inflammatory and lipid-modulating effects.

Punicic acid is a polyunsaturated fatty acid, 18:3 cis-9, trans-11, cis-13.
Punicic acid is named for the pomegranate, (Punica granatum), and is obtained from pomegranate seed oil.
Punicic acid has also been found in the seed oils of snake gourd.

Punicic acid is a conjugated linolenic acid or CLnA; i.e. it has three conjugated double bonds.
Punicic acid is chemically similar to the conjugated linoleic acids, or CLA, which have two.

Punicic acid has also been classified as an "n-5" or "omega-5" polyunsaturated fatty acid.
In lab rats, punicic acid was converted to the CLA rumenic acid (9Z11E-CLA).

In vitro, Punicic acid shows anti-invasive activity against prostate cancer cells.
OLETF rats—a strain which becomes obese—remained relatively lean when punicic acid was added to their feed.

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.

Punicic acid is defined as a conjugated linolenic acid primarily found in pomegranate seeds, known for its anticarcinogenic effects and potential role in reducing white adipose tissue weight in rodents.

Uses of Punicic Acid:
Punicic acid is used in nutraceuticals and dietary supplements to provide antioxidant support and contribute to metabolic health.
Punicic acid is incorporated into functional foods and edible oils to enhance nutritional value and deliver bioactive lipid benefits.

Punicic acid is applied in cosmetic and personal care products such as creams, serums, and oils to improve skin elasticity, hydration, and anti-aging performance.
Punicic acid is also utilized in pharmaceutical and biomedical research for its potential roles in anti-inflammatory activity, lipid metabolism regulation, and overall health support.

Benefits of Punicic Acid:
Punicic acid provides strong antioxidant activity, helping to protect cells from oxidative stress.
Punicic acid supports anti-inflammatory effects, contributing to overall health and wellness.

Punicic acid promotes skin health by improving elasticity, hydration, and reducing signs of aging.
Punicic acid may support lipid metabolism and help maintain healthy cholesterol balance.

Punicic acid contributes to improved metabolic function and may aid in weight management support.
Punicic acid supports immune system function through its bioactive properties.
Punicic acid enhances the nutritional value of functional foods and supplements due to its unique fatty acid profile.

Stability and Reactivity of Punicic Acid:

Chemical stability:
Punicic acid is moderately stable.
Prone to oxidation due to its conjugated double bond structure.

Reactivity:
Reacts with oxygen.
Reacts with free radicals.
Undergoes auto-oxidation.

Conditions to avoid:
Heat.
Light.
Air exposure.
Prolonged storage without antioxidants.

Incompatible materials:
Strong oxidizing agents.

Hazardous decomposition products:
Carbon oxides (CO, CO₂) may form.
Irritating organic fumes may be released.

Handling and Storage of Punicic Acid:

Handling:
Handle with care to minimize exposure to air and light.
Avoid prolonged contact with skin and eyes.

Storage:
Store in tightly closed containers in a cool, dry, and dark environment.

Storage conditions:
Protect from oxygen.
Protect from heat.

Protect from UV light.
Use inert gas such as nitrogen for long-term storage.

Packaging materials:
Use airtight and light-resistant containers.

Shelf life:
Limited.
Stability improves with antioxidants and proper storage conditions.

First Aid Measures of Punicic Acid:

Inhalation:
Not typically hazardous.
Move to fresh air if exposure occurs.

Skin contact:
Wash thoroughly with soap and water.

Eye contact:
Rinse cautiously with water for several minutes.

Ingestion:
Generally safe as a natural component.
Seek medical advice if discomfort occurs.

Most important symptoms:
Mild irritation may occur with prolonged exposure.

Firefighting Measures of Punicic Acid:

Suitable extinguishing media:
Foam.
Dry chemical powder.
Carbon dioxide (CO₂).

Specific hazards:
Combustible organic liquid.
May emit irritating fumes upon burning.

Protective equipment for firefighters:
Use self-contained breathing apparatus.
Wear protective clothing.

Special precautions:
Avoid inhalation of combustion products.

Accidental Release Measures of Punicic Acid:

Personal precautions:
Avoid contact.
Prevent slipping hazards.

Environmental precautions:
Prevent large quantities from entering drains or water systems.

Methods for cleanup:
Absorb with inert material such as sand or vermiculite.
Collect for disposal.

Exposure Controls / Personal Protection of Punicic Acid:

Occupational exposure limits:
Not established.

Engineering controls:
General ventilation is sufficient.

Respiratory protection:
Not normally required.

Hand protection:
Use protective gloves.

Eye protection:
Use safety glasses.

Skin protection:
Wear standard protective clothing.

Hygiene measures:
Wash hands after handling.
Avoid unnecessary exposure.

Identifiers of Punicic Acid:
IUPAC Name: (9Z,11E,13Z)-octadeca-9,11,13-trienoic acid
CAS Number: 65999-44-0
EC Number: Not widely assigned
Molecular Formula: C₁₈H₃₀O₂
Molecular Weight: 278.43 g/mol
Chemical Class: Conjugated linolenic acid (CLnA)
Structure Type: Conjugated polyunsaturated fatty acid
Functional Groups: Carboxylic acid (-COOH), conjugated double bonds

CAS Number: 544-72-9
ChEBI: CHEBI:8638
ChemSpider: 4444570
PubChem CID: 5281126
UNII: VFQ03H211O
CompTox Dashboard (EPA): DTXSID10897463
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-
Key: CUXYLFPMQMFGPL-BGDVVUGTSA-N
InChI=1/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-
Key: CUXYLFPMQMFGPL-BGDVVUGTBE
SMILES: CCCCC=C/C=C/C=CCCCCCCCC(=O)O

Properties of Punicic Acid:
Chemical formula: C18H30O2
Molar mass: 278.43 g/mol
Melting point: 44 to 45 °C (111 to 113 °F; 317 to 318 K)

Appearance: Pale yellow to amber oily liquid
Odor: Mild, fatty characteristic
Melting Point: ~44–46°C
Boiling Point: Not well-defined; decomposes at high temperature
Density: ~0.91–0.93 g/cm³
Viscosity: Moderate
Refractive Index: ~1.48–1.50
Acid Value: High
Iodine Value: High due to conjugated unsaturation

Molecular Weight: 278.4 g/mol
XLogP3: 6.4
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 13
Exact Mass: 278.224580195 Da
Monoisotopic Mass: 278.224580195 Da
Topological Polar Surface Area: 37.3 Å²
Heavy Atom Count: 20
Complexity: 301
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 3
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Names of Punicic Acid:

Preferred IUPAC name:
(9Z,11E,13Z)-Octadeca-9,11,13-trienoic acid