Sarracine

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 461832

CAS#: 2492-09-3

Description: Sarracine is a pyrrolizidine alkaloid and saturated diester.


Chemical Structure

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Sarracine
CAS# 2492-09-3

Theoretical Analysis

MedKoo Cat#: 461832
Name: Sarracine
CAS#: 2492-09-3
Chemical Formula: C18H27NO5
Exact Mass: 337.1889
Molecular Weight: 337.41
Elemental Analysis: C, 64.07; H, 8.07; N, 4.15; O, 23.71

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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

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

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.

Recalculate based on batch purity %
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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Reconstitution Calculator

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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.