Synonym
Rinderine; O-Demethylheliotrine; Heliotridine trachelanthate; 9-(+)-Trachelanthylheliotridine
IUPAC/Chemical Name
((1S,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl (2S)-2,3-dihydroxy-2-isopropylbutanoate
InChi Key
SFVVQRJOGUKCEG-LLTIUZATSA-N
InChi Code
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
SMILES Code
O[C@H]1CCN2CC=C(COC([C@](C(O)C)(O)C(C)C)=O)[C@@H]21
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
299.36
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
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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.
