Global InformationSolenopsin information
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| Preferred IUPAC name
(2R,6R)-2-Methyl-6-undecylpiperidine[1] | |
| Other names
Solenopsin A
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3D model (JSmol)
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CompTox Dashboard (EPA)
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| Properties | |
Chemical formula
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C17H35N |
| Molar mass | 253.474 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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Solenopsin is a lipophilic alkaloid with the molecular formula C17H35N found in the venom of fire ants (Solenopsis). It is considered the primary toxin in the venom[2] and may be the component responsible for the cardiorespiratory failure in people who experience excessive fire ant stings.[3]
Structurally solenopsins are a piperidine ring with a methyl group substitution at position 2 and a long hydrophobic chain at position 6. They are typically oily at room temperature, water-insoluble, and present an absorbance peak at 232 nanometers.[4] Fire ant venom contains other chemically related piperidines which make purification of solenopsin from ants difficult.[5][6] Therefore, solenopsin and related compounds have been the target of organic synthesis from which pure compounds can be produced for individual study. Originally synthesized in 1993,[7] several groups have designed novel and creative methods of synthesizing enantiopure solenopsin and other alkaloidal components of ant venom.
- ^ Stereochemistry per: Leclercq S, Thirionet I, Broeders F, Daloze D, Vander Meer R, Braekman J (1994). "Absolute configuration of the solenopsins, venom alkaloids of the fire ants". Tetrahedron. 50 (28): 8465–8478. doi:10.1016/S0040-4020(01)85567-8.
- ^ Touchard A, Aili SR, Fox EG, Escoubas P, Orivel J, Nicholson GM, Dejean A (2016). "The Biochemical Toxin Arsenal from Ant Venoms". Toxins. 8 (1): 30. doi:10.3390/toxins8010030. PMC 4728552. PMID 26805882.
- ^ Howell G, Butler J, Deshazo RD, Farley JM, Liu HL, Nanayakkara NP, Yates A, Yi GB, Rockhold RW (2005). "Cardiodepressant and neurologic actions of Solenopsis invicta (imported fire ant) venom alkaloids". Ann Allergy Asthma Immunol. 94 (3): 380–6. doi:10.1016/S1081-1206(10)60991-X. PMID 15801250.
- ^ Fox EG, Xu M, Wang L, Chen L, Lu YY (June 2018). "Gas-chromatography and UV-spectroscopy of Hymenoptera venoms obtained by trivial centrifugation". Data in Brief. 18: 992–998. Bibcode:2018DIB....18..992F. doi:10.1016/j.dib.2018.03.101. PMC 5996826. PMID 29900266.
- ^ Gopalakrishnakone P, Calvete JJ (2021-01-14). Venom genomics and proteomics. Gopalakrishnakone, P.,, Calvete, Juan J. (Living Reference Work ed.). Dordrecht. ISBN 9789400766495. OCLC 968345667.
{{cite book}}: CS1 maint: location missing publisher (link) - ^ Fox EG, Xu M, Wang L, Chen L, Lu YY (May 2018). "Speedy milking of fresh venom from aculeate hymenopterans". Toxicon. 146: 120–123. doi:10.1016/j.toxicon.2018.02.050. PMID 29510162.
- ^ Jefford CW, Bo Wang J (30 April 1993). "An enantiospecific synthesis of solenopsin A". Tetrahedron Letters. 34 (18): 2911–2914. doi:10.1016/S0040-4039(00)60479-3. Retrieved 20 April 2021.