Trideca-7,9,11-trienoic acid

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Trideca-7,9,11-trienoic acid
Trideca-7,9,11-trienoic acid.svg
Trideca-7,9,11-trienoic acid.png
Names
IUPAC name
(7E,9E,11E)-Trideca-7,9,11-trienoic acid
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • 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
  • C/C=C/C=C/C=C/CCCCCC(=O)O
Properties
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).

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]

Contents

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. 1 2 3 4 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. ↑ 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)
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