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Trideca-7,9,11-trienoic acid

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Trideca-7,9,11-trienoic acid
Names
IUPAC name (7E,9E,11E)-Trideca-7,9,11-trienoic acid
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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.

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.

Similar compounds

Trideca-7,9,11-trienoic acid is somewhat similiar to palmitoylethanolamide and anandamide (endocannabinoid) in that they are both have a long carbon chain, a double-bonded oxygen and a hydroxyl group. In a 2017 systematic meta-analysis involving 10 studies including data from 786 patients receiving palmitoylethanolamide for pain-related indications and 512 controls, PEA was found to be associated with pain reduction significantly greater than observed in controls (P < 0.001).

Trideca-7,9,11-trienoic acid is also somewhat similiar to oleamide in that both of them have an unsaturated carbon chain and an oxygen with a double bond. Oleamide also has anxiolytic effects, but its specific pharmacological mechanism of action is unknown.

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.

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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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. Artukoglu BB, Beyer C, Zuloff-Shani A, Brener E, Bloch MH (July 2017). "Efficacy of Palmitoylethanolamide for Pain: A Meta-Analysis". Pain Physician. 20 (5): 353–362. PMID 28727699.
  8. Hiley, C. Robin; Hoi, Pui Man (13 April 2007). "Oleamide: A Fatty Acid Amide Signaling Molecule in the Cardiovascular System?: OLEAMIDE". Cardiovascular Drug Reviews. 25 (1): 46–60. doi:10.1111/j.1527-3466.2007.00004.x. PMID 17445087.
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