Jaconine

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

MedKoo CAT#: 596084

CAS#: 480-75-1

Description: Jaconine a pyrrolizidine alkaloid.


Chemical Structure

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Jaconine
CAS# 480-75-1

Theoretical Analysis

MedKoo Cat#: 596084
Name: Jaconine
CAS#: 480-75-1
Chemical Formula: C18H26ClNO6
Exact Mass: 387.1449
Molecular Weight: 387.85
Elemental Analysis: C, 55.74; H, 6.76; Cl, 9.14; N, 3.61; O, 24.75

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: Jaconine; 4-27-00-06661 (Beilstein Handbook Reference); BRN 0056049; BRN-0056049; BRN0056049;

IUPAC/Chemical Name: (3R,5R,6S,9a1R,14aR)-3-((R)-1-chloroethyl)-3,6-dihydroxy-5,6-dimethyl-3,4,5,6,9,9a1,11,13,14,14a-decahydro-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione

InChi Key: CKPJPJSVQMEGBC-HRKZPBNPSA-N

InChi Code: InChI=1S/C18H26ClNO6/c1-10-8-18(24,11(2)19)16(22)26-13-5-7-20-6-4-12(14(13)20)9-25-15(21)17(10,3)23/h4,10-11,13-14,23-24H,5-9H2,1-3H3/t10-,11-,13-,14-,17+,18+/m1/s1

SMILES Code: O=C(O[C@]1([H])CCN2[C@]1([H])C(CO3)=CC2)[C@@](O)([C@H](Cl)C)C[C@@H](C)[C@](C)(O)C3=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: >2 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: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 387.85 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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1: Nuringtyas TR, Choi YH, Verpoorte R, Klinkhamer PG, Leiss KA. Differential tissue distribution of metabolites in Jacobaea vulgaris, Jacobaea aquatica and their crosses. Phytochemistry. 2012 Jun;78:89-97. doi: 10.1016/j.phytochem.2012.03.011. Epub 2012 Apr 18. PubMed PMID: 22516740.

2: Cheng D, Kirk H, Vrieling K, Mulder PP, Klinkhamer PG. The relationship between structurally different pyrrolizidine alkaloids and western flower thrips resistance in F(2) hybrids of Jacobaea vulgaris and Jacobaea aquatica. J Chem Ecol. 2011 Oct;37(10):1071-80. doi: 10.1007/s10886-011-0021-6. Epub 2011 Oct 4. PubMed PMID: 21969251; PubMed Central PMCID: PMC3197926.

3: Ma H, Yang L, Wang C, Wang Z. [Pyrrolizidine alkaloids of Senecio cannabifolius var. integrilifolius]. Zhongguo Zhong Yao Za Zhi. 2011 Jan;36(2):166-8. Chinese. PubMed PMID: 21506416.

4: Joosten L, Cheng D, Mulder PP, Vrieling K, van Veen JA, Klinkhamer PG. The genotype dependent presence of pyrrolizidine alkaloids as tertiary amine in Jacobaea vulgaris. Phytochemistry. 2011 Feb;72(2-3):214-22. doi: 10.1016/j.phytochem.2010.11.013. Epub 2010 Dec 13. PubMed PMID: 21159354.

5: Leiss KA, Choi YH, Abdel-Farid IB, Verpoorte R, Klinkhamer PG. NMR metabolomics of thrips (Frankliniella occidentalis) resistance in Senecio hybrids. J Chem Ecol. 2009 Feb;35(2):219-29. doi: 10.1007/s10886-008-9586-0. Epub 2009 Jan 24. PubMed PMID: 19169751.

6: Tundis R, Loizzo MR, Statti GA, Passalacqua NG, Peruzzi L, Menichini F. Pyrrolizidine alkaloid profiles of the Senecio cineraria group (Asteraceae). Z Naturforsch C. 2007 Jul-Aug;62(7-8):467-72. PubMed PMID: 17913058.

7: Wiedenfeld H, Montes C, Tawil B, Contin A, Wynsma R. Pyrrolizidine alkaloid level in Senecio bicolor (Wilid.) Tod, ssp. cineraria (DC.) from middle Europe. Pharmazie. 2006 Jun;61(6):559-61. PubMed PMID: 16826978.

8: Crews C, Startin JR, Clarke PA. Determination of pyrrolizidine alkaloids in honey from selected sites by solid phase extraction and HPLC-MS. Food Addit Contam. 1997 Jul;14(5):419-28. PubMed PMID: 9328525.

9: Deinzer ML, Thomson PA, Burgett DM, Isaacson DL. Pyrrolizidine alkaloids: their occurrence in honey from tansy ragwort (Senecio jacobaea L.) Science. 1977 Feb 4;195(4277):497-9. PubMed PMID: 835011.