Trideca-7,9,11-trienoic acid

Trideca-7,9,11-trienoic acid

Names
IUPAC name (7E,9E,11E)-Trideca-7,9,11-trienoic acid
Identifiers
3D model (JSmol)	Interactive image
ChemSpider	28288114^Y
PubChem CID	88499374
InChI InChI=1S/C13H20O2/c1-2-3-4-5-6-7-8-9-10-11-12-13(14)15/h2-7H,8-12H2,1H3,(H,14,15)/b3-2+,5-4+,7-6+¨ Key: CMKVWQNTXKWDNT-ICDJNDDTSA-N
SMILES C/C=C/C=C/C=C/CCCCCC(=O)O
Properties
Chemical formula	C13H20O2
Molar mass	208.301 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Trideca-7,9,11-trienoic acid, or (7E,9E,11E)-trideca-7,9,11-trienoic acid, is an polyunsaturated fatty acid. It is present in Aethusa cynapium.[1][2][3]

Pharmacology

Trideca-7,9,11-trienoic acid has been shown to have an antianxiety effect in Mus musculus, Rattus norvegicus, and Homo sapiens. It reduces hypolocomotion caused by anxiety, which was psychopharmacologically induced with mCPP, in Mus musculus and Rattus norvegicus. A 2 mg/kg dose of diazepam has a very similar effect to 20 mg/kg of trideca-7,9,11-trienoic acid. This may suggest that trideca-7,9,11-trienoic acid is also a GABA agonist like diazepam.[1][4][5][6]

Extraction from A. cynapium

Trideca-7,9,11-trienoic acid can be extracted from dried aerial parts of A. cynapium with methanol, followed by chloroform, followed by column chromatography with DCM and methanol (40:60), followed by flash chromatography with DCM and methanol (92.5:7.5), followed by preparative TLC.[1]

Uses

In addition to its potential as an anxiolytic, trideca-7,9,11-trienoic acid has also been studied for use in inks and protective coatings.[1][7]

References

1. Shri, Richa; Bhutani, K.K.; Sharma, Anupam (2010). "A new anxiolytic fatty acid from Aethusa cynapium". Fitoterapia. 81 (5): 337–340. doi:10.1016/j.fitote.2010.05.003. PMID 20472038. (https://www.academia.edu/4694323/A_new_anxiolytic_fatty_acid_from_Aethusa_cynapium)
2. "(7E,9E,11E)-trideca-7,9,11-trienoic acid". PubChem. National Library of Medicine. 3.1.2025.
3. EP0503897A1, Gerald Sugarman, Michael W. O'Neill, "Composition for ink vehicles and protective coatings", assigned to Topez Co  16.9.1992.
4. Bilkei-Gorzo A, Gyertyar I, Szabados T (1996). "mCPP-induced anxiety—a potential new method for screening anxiolytic activity". Neurobiology. 4: 253–5.
5. Bilkei-Gorzo A, Gyertyar I, Levay G (1998). "mCPP-induced anxiety in the light–dark box in rats—a new method for screening anxiolytic activity". Psychopharmacology. 136 (3): 291–8. doi:10.1007/s002130050568. PMID 9566815.
6. Riss J, Cloyd J, Gates J, Collins S (August 2008). "Benzodiazepines in epilepsy: pharmacology and pharmacokinetics". Acta Neurologica Scandinavica. 118 (2): 69–86. doi:10.1111/j.1600-0404.2008.01004.x. PMID 18384456. S2CID 24453988.
7. Composition for ink vehicles and protective coatings, European Patent Office, EP0503897A1, Gerald SugarmanMichael W. O'neill, 16.9.1992. (https://patents.google.com/patent/EP0503897A1)