Jaconine hydrochloride

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

MedKoo CAT#: 596090

CAS#: 7251-11-8

Description: Jaconine hydrochloride is a Pyrrolizidine alkaloid.


Chemical Structure

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Jaconine hydrochloride
CAS# 7251-11-8

Theoretical Analysis

MedKoo Cat#: 596090
Name: Jaconine hydrochloride
CAS#: 7251-11-8
Chemical Formula: C18H27Cl2NO6
Exact Mass: 423.1215
Molecular Weight: 424.31
Elemental Analysis: C, 50.95; H, 6.41; Cl, 16.71; N, 3.30; O, 22.62

Size Price Shipping out time Quantity
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Pricing updated 2021-03-05. Prices are subject to change without notice.

Jaconine hydrochloride is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.

Synonym: Jaconine hydrochloride; Jaconine HCl; NSC 30624; NSC-30624; NSC30624;

IUPAC/Chemical Name: (3R,5R,6R,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 hydrochloride

InChi Key: AOFLJXYFSXFMOL-QTUOXSIISA-N

InChi Code: InChI=1S/C18H26ClNO6.ClH/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;1H/t10-,11-,13-,14-,17-,18+;/m1./s1

SMILES Code: [H][C@@]12[C@]([H])(OC([C@@](C[C@H]([C@]3(O)C)C)(O)[C@H](Cl)C)=O)CCN1CC=C2COC3=O.[H]Cl

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

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 424.31 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.

Select a batch to recalculate based on the batch molecular weight:
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.