Synonym
Sarracine; Sarracin;
IUPAC/Chemical Name
(1R,7S,7aR)-7-((((Z)-2-(hydroxymethyl)but-2-enoyl)oxy)methyl)hexahydro-1H-pyrrolizin-1-yl (Z)-2-methylbut-2-enoate
InChi Key
YMUQRQKYYOWGPN-SLEGRLQASA-N
InChi Code
InChI=1S/C18H27NO5/c1-4-12(3)17(21)24-15-7-9-19-8-6-14(16(15)19)11-23-18(22)13(5-2)10-20/h4-5,14-16,20H,6-11H2,1-3H3/b12-4-,13-5-/t14-,15-,16-/m1/s1
SMILES Code
C/C=C(CO)\C(OC[C@@H]1[C@]2([H])[C@H](OC(/C(C)=C\C)=O)CCN2CC1)=O
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
337.41
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 |
1: MURAVEVA DA. [PLATYPHYLLINE AND SARRACINE AND THEIR RAW SOURCES]. Med Prom SSSR. 1964 Aug;18:14-8. Russian. PubMed PMID: 14255286.
2: Villanueva-Cañongo C, Pérez-Hernández N, Hernández-Carlos B, Cedillo-Portugal E, Joseph-Nathan P, Burgueño-Tapia E. Complete 1H NMR assignments of pyrrolizidine alkaloids and a new eudesmanoid from Senecio polypodioides. Magn Reson Chem. 2014 May;52(5):251-7. doi: 10.1002/mrc.4054. Epub 2014 Feb 27. PubMed PMID: 24574143.
3: Egorova EI. [Detection of platyphylline, sarracine and seneciphylline in biological material]. Sud Med Ekspert. 1967 Apr-Jun;10(2):36-40. Russian. PubMed PMID: 5608363.
4: Stelljes ME, Seiber JN. Pyrrolizidine alkaloids in an overwintering population of monarch butterflies (Danaus plexippus) in California. J Chem Ecol. 1990 May;16(5):1459-70. doi: 10.1007/BF01014081. PubMed PMID: 24263818.
5: Egorova EI. [A method for the determination of sarracine and its relation to pH of the medium and the nature of the organic solvent]. Sud Med Ekspert. 1965 Apr-Jun;8(2):24-7. Russian. PubMed PMID: 5854988.
6: Maksimova TV, Drozdov VA, Loshkarev PM, Kreshkov AP. [Analysis of sarracine bitartrate, gindarin, solasodine citrate and "Saparal" tablets by titration in nonaqueous media]. Farmatsiia. 1974 Nov-Dec;(6):51-3. Russian. PubMed PMID: 4464122.
7: Christov V, Mikhova B, Alexandrova R, Dimitrova D, Nikolova E, Evstatieva L. Alkaloids from the roots of Senecio macedonicus Griseb. Z Naturforsch C. 2002 Sep-Oct;57(9-10):780-4. PubMed PMID: 12440711.
8: Pomeroy AR, Raper C. Pyrrolizidine alkaloids: actions on muscarinic receptors in the guinea-pig ileum. Br J Pharmacol. 1971 Apr;41(4):683-90. PubMed PMID: 5579465; PubMed Central PMCID: PMC1702759.
9: Hartmann T, Theuring C, Beuerle T, Bernays EA, Singer MS. Acquisition, transformation and maintenance of plant pyrrolizidine alkaloids by the polyphagous arctiid Grammia geneura. Insect Biochem Mol Biol. 2005 Oct;35(10):1083-99. PubMed PMID: 16102415.
