Rinderine

For research use only. Not for therapeutic Use.

  • CAT Number: I035587
  • CAS Number: 6029-84-1
  • Molecular Formula: C15H25NO5
  • Molecular Weight: 299.36
  • Purity: 98%
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Rinderine is a dehydropyrrolizidine alkaloid monoester.


Catalog Number I035587
CAS Number 6029-84-1
Synonyms

Rinderine; O-Demethylheliotrine;

Molecular Formula C15H25NO5
Purity 98%
Target Plants
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name ((1S,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl (2S)-2,3-dihydroxy-2-isopropylbutanoate
InChI InChI=1S/C15H25NO5/c1-9(2)15(20,10(3)17)14(19)21-8-11-4-6-16-7-5-12(18)13(11)16/h4,9-10,12-13,17-18,20H,5-8H2,1-3H3/t10?,12-,13+,15-/m0/s1
InChIKey SFVVQRJOGUKCEG-LLTIUZATSA-N
SMILES O[C@H]1CCN2CC=C(COC([C@](C(O)C)(O)C(C)C)=O)[C@@H]21
Reference

1: Colegate SM, Boppré M, Monzón J, Betz JM. Pro-toxic dehydropyrrolizidine alkaloids in the traditional Andean herbal medicine "asmachilca". J Ethnopharmacol. 2015 Aug 22;172:179-94. doi: 10.1016/j.jep.2015.06.012. Epub 2015 Jun 16. PubMed PMID: 26087231; PubMed Central PMCID: PMC4523498.
2: Boppré M, Colegate SM. Recognition of pyrrolizidine alkaloid esters in the invasive aquatic plant Gymnocoronis spilanthoides (Asteraceae). Phytochem Anal. 2015 May-Jun;26(3):215-25. doi: 10.1002/pca.2555. Epub 2015 Jan 27. PubMed PMID: 25645745.
3: Shimshoni JA, Mulder PP, Bouznach A, Edery N, Pasval I, Barel S, Abd-El Khaliq M, Perl S. Heliotropium europaeum poisoning in cattle and analysis of its pyrrolizidine alkaloid profile. J Agric Food Chem. 2015 Feb 11;63(5):1664-72. doi: 10.1021/jf5052199. Epub 2015 Jan 27. PubMed PMID: 25591008.
4: Mandić BM, Vlajić MD, Trifunović SS, Simić MR, Vujisić LV, VuČković IM, Novaković MM, Nikolić-Mandić SD, Tešević VV, Vajs VV, Milosavljević SM. Optimisation of isolation procedure for pyrrolizidine alkaloids from Rindera umbellata Bunge. Nat Prod Res. 2015;29(9):887-90. doi: 10.1080/14786419.2014.991929. Epub 2014 Dec 20. PubMed PMID: 25528897.
5: Colegate SM, Gardner DR, Betz JM, Panter KE. Semi-automated separation of the epimeric dehydropyrrolizidine alkaloids lycopsamine and intermedine: preparation of their N-oxides and NMR comparison with diastereoisomeric rinderine and echinatine. Phytochem Anal. 2014 Sep-Oct;25(5):429-38. doi: 10.1002/pca.2511. Epub 2014 May 9. PubMed PMID: 24816769.
6: Trigo JR, Witte L, Brown KS Jr, Hartmann T, Barata LE. Pyrrolizidine alkaloids in the arctiid mothHyalurga syma. J Chem Ecol. 1993 Apr;19(4):669-79. doi: 10.1007/BF00985000. PubMed PMID: 24249009.
7: Asibal CF, Glinski JA, Gelbaum LT, Zalkow LH. Pyrrolizidine alkaloids from Cynoglossum creticum. Synthesis of the pyrrolizidine alkaloids echinatine, rinderine, and analogues. J Nat Prod. 1989 Jan-Feb;52(1):109-18. PubMed PMID: 2597280.

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