Volicitin

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MedKoo CAT#: 597299

CAS#: 191670-18-5

Description: Volicitin is an elicitor that triggers emission of volatile from plants.


Price and Availability

Size Price Shipping out time Quantity
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Pricing updated 2020-08-11. Prices are subject to change without notice.

Volicitin is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 597299
Name: Volicitin
CAS#: 191670-18-5
Chemical Formula: C23H38N2O5
Exact Mass: 422.2781
Molecular Weight: 422.56
Elemental Analysis: C, 65.38; H, 9.06; N, 6.63; O, 18.93


Synonym: Volicitin; (17S)-Volicitin;

IUPAC/Chemical Name: ((S,9Z,12Z,15Z)-17-hydroxyoctadeca-9,12,15-trienoyl)-L-glutamine

InChi Key: YDUZXFXPORORCL-CKBPCMIVSA-N

InChi Code: InChI=1S/C23H38N2O5/c1-19(26)15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-22(28)25-20(23(29)30)17-18-21(24)27/h2-3,7,9,13,15,19-20,26H,4-6,8,10-12,14,16-18H2,1H3,(H2,24,27)(H,25,28)(H,29,30)/b3-2-,9-7-,15-13-/t19-,20-/m0/s1

SMILES Code: O=C(N)CC[C@@H](C(O)=O)NC(CCCCCCC/C=C\C/C=C\C/C=C\[C@@H](O)C)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.03.00


References

1: LeClair G, Williams M, Silk P, Eveleigh E, Mayo P, Brophy M, Francis B. Spruce Budworm (Lepidoptera: Tortricidae) Oral Secretions II: Chemistry. Environ Entomol. 2015 Dec;44(6):1531-43. doi: 10.1093/ee/nvv149. Epub 2015 Oct 9. PubMed PMID: 26454474.

2: Yoshinaga N, Ishikawa C, Seidl-Adams I, Bosak E, Aboshi T, Tumlinson JH, Mori N. N-(18-hydroxylinolenoyl)-L-glutamine: a newly discovered analog of volicitin in Manduca sexta and its elicitor activity in plants. J Chem Ecol. 2014 May;40(5):484-90. doi: 10.1007/s10886-014-0436-y. Epub 2014 May 11. PubMed PMID: 24817386.

3: Bonaventure G, VanDoorn A, Baldwin IT. Herbivore-associated elicitors: FAC signaling and metabolism. Trends Plant Sci. 2011 Jun;16(6):294-9. doi: 10.1016/j.tplants.2011.01.006. Epub 2011 Feb 25. PubMed PMID: 21354852.

4: Yoshinaga N, Alborn HT, Nakanishi T, Suckling DM, Nishida R, Tumlinson JH, Mori N. Fatty acid-amino acid conjugates diversification in lepidopteran caterpillars. J Chem Ecol. 2010 Mar;36(3):319-25. doi: 10.1007/s10886-010-9764-8. Epub 2010 Feb 27. PubMed PMID: 20195891.

5: Ishikawa C, Yoshinaga N, Aboshi T, Nishida R, Mori N. Efficient incorporation of free oxygen into volicitin in Spodoptera litura common cutworm larvae. Biosci Biotechnol Biochem. 2009 Aug;73(8):1883-5. Epub 2009 Aug 7. PubMed PMID: 19661708.

6: Schmelz EA, Engelberth J, Alborn HT, Tumlinson JH 3rd, Teal PE. Phytohormone-based activity mapping of insect herbivore-produced elicitors. Proc Natl Acad Sci U S A. 2009 Jan 13;106(2):653-7. doi: 10.1073/pnas.0811861106. Epub 2009 Jan 5. PubMed PMID: 19124770; PubMed Central PMCID: PMC2626758.

7: Yoshinaga N, Aboshi T, Abe H, Nishida R, Alborn HT, Tumlinson JH, Mori N. Active role of fatty acid amino acid conjugates in nitrogen metabolism in Spodoptera litura larvae. Proc Natl Acad Sci U S A. 2008 Nov 18;105(46):18058-63. doi: 10.1073/pnas.0809623105. Epub 2008 Nov 7. PubMed PMID: 18997016; PubMed Central PMCID: PMC2584681.

8: Yoshinaga N, Aboshi T, Ishikawa C, Fukui M, Shimoda M, Nishida R, Lait CG, Tumlinson JH, Mori N. Fatty acid amides, previously identified in caterpillars, found in the cricket Teleogryllus taiwanemma and fruit fly Drosophila melanogaster larvae. J Chem Ecol. 2007 Jul;33(7):1376-81. PubMed PMID: 17566833.

9: Aboshi T, Yoshinaga N, Noge K, Nishida R, Mori N. Efficient incorporation of unsaturated fatty acids into volicitin-related compounds in Spodoptera litura (Lepidoptera: Noctuidae). Biosci Biotechnol Biochem. 2007 Feb;71(2):607-10. Epub 2007 Feb 7. PubMed PMID: 17284824.

10: Major IT, Constabel CP. Molecular analysis of poplar defense against herbivory: comparison of wound- and insect elicitor-induced gene expression. New Phytol. 2006;172(4):617-35. PubMed PMID: 17096789.

11: Sawada Y, Yoshinaga N, Fujisaki K, Nishida R, Kuwahara Y, Mori N. Absolute configuration of volicitin from the regurgitant of lepidopteran caterpillars and biological activity of volicitin-related compounds. Biosci Biotechnol Biochem. 2006 Sep;70(9):2185-90. Epub 2006 Sep 7. PubMed PMID: 16960380.

12: Paré PW, Farag MA, Krishnamachari V, Zhang H, Ryu CM, Kloepper JW. Elicitors and priming agents initiate plant defense responses. Photosynth Res. 2005 Aug;85(2):149-59. Review. PubMed PMID: 16075316.

13: Lawrence SD, Novak NG. Maize genes induced by herbivory and volicitin. J Chem Ecol. 2004 Dec;30(12):2543-57. PubMed PMID: 15724970.

14: Yoshinaga N, Morigaki N, Matsuda F, Nishida R, Mori N. In vitro biosynthesis of volicitin in Spodoptera litura. Insect Biochem Mol Biol. 2005 Feb;35(2):175-84. Erratum in: Insect Biochem Mol Biol. 2005 Aug;35(8):945. PubMed PMID: 15681227.

15: De Moraes CM, Mescher MC. Biochemical crypsis in the avoidance of natural enemies by an insect herbivore. Proc Natl Acad Sci U S A. 2004 Jun 15;101(24):8993-7. Epub 2004 Jun 7. PubMed PMID: 15184664; PubMed Central PMCID: PMC428460.

16: Frey M, Spiteller D, Boland W, Gierl A. Transcriptional activation of Igl, the gene for indole formation in Zea mays: a structure-activity study with elicitor-active N-acyl glutamines from insects. Phytochemistry. 2004 Apr;65(8):1047-55. PubMed PMID: 15110684.

17: Maffei M, Bossi S, Spiteller D, Mithöfer A, Boland W. Effects of feeding Spodoptera littoralis on lima bean leaves. I. Membrane potentials, intracellular calcium variations, oral secretions, and regurgitate components. Plant Physiol. 2004 Apr;134(4):1752-62. Epub 2004 Mar 29. PubMed PMID: 15051862; PubMed Central PMCID: PMC419848.

18: Yoshinaga N, Sawada Y, Nishida R, Kuwahara Y, Mori N. Specific incorporation of L-glutamine into volicitin in the regurgitant of Spodoptera litura. Biosci Biotechnol Biochem. 2003 Dec;67(12):2655-7. PubMed PMID: 14730148.

19: Truitt CL, Wei HX, Paré PW. A plasma membrane protein from Zea mays binds with the herbivore elicitor volicitin. Plant Cell. 2004 Feb;16(2):523-32. Epub 2004 Jan 16. PubMed PMID: 14729912; PubMed Central PMCID: PMC341921.

20: Truitt CL, Paré PW. In situ translocation of volicitin by beet armyworm larvae to maize and systemic immobility of the herbivore elicitor in planta. Planta. 2004 Apr;218(6):999-1007. Epub 2003 Dec 18. PubMed PMID: 14685859.