WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 596088
CAS#: 5532-23-0
Description: Jacozine is an alkaloid found in ragwort.
MedKoo Cat#: 596088
Name: Jacozine
CAS#: 5532-23-0
Chemical Formula: C18H23NO6
Exact Mass: 349.1525
Molecular Weight: 349.38
Elemental Analysis: C, 61.88; H, 6.64; N, 4.01; O, 27.48
This product is not in stock, which may be available by custom synthesis.
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Synonym: Jacozine;
IUPAC/Chemical Name: (2S,3S,6'R,9a1'R,14a'R)-6'-hydroxy-3,6'-dimethyl-5'-methylene-5',6',9',9a1',11',13',14',14a'-octahydro-2'H-spiro[oxirane-2,3'-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine]-2',7'(4'H)-dione
InChi Key: XCEPKQNOWNOSFH-CGPXFRKCSA-N
InChi Code: InChI=1S/C18H23NO6/c1-10-8-18(11(2)25-18)16(21)24-13-5-7-19-6-4-12(14(13)19)9-23-15(20)17(10,3)22/h4,11,13-14,22H,1,5-9H2,2-3H3/t11-,13+,14+,17+,18-/m0/s1
SMILES Code: O=C(O[C@]1([H])CCN2[C@]1([H])C(COC([C@@]3(O)C)=O)=CC2)[C@]4(O[C@H]4C)CC3=C
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
The following data is based on the product molecular weight 349.38 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: 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.
2: Li SL, Lin G, Fu PP, Chan CL, Li M, Jiang ZH, Zhao ZZ. Identification of five hepatotoxic pyrrolizidine alkaloids in a commonly used traditional Chinese medicinal herb, Herba Senecionis scandentis (Qianliguang). Rapid Commun Mass Spectrom. 2008;22(4):591-602. doi: 10.1002/rcm.3398. PubMed PMID: 18220326.
3: 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.
4: Christov VS, Mikhova BP, Evstatieva LN. Alkaloids from Senecio aquaticus. Fitoterapia. 2002 Apr;73(2):171-3. PubMed PMID: 11978435.
5: 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.
6: Dueker SR, Lamé MW, Segall HJ. Hydrolysis rates of pyrrolizidine alkaloids derived from Senecio jacobaea. Arch Toxicol. 1995;69(10):725-8. PubMed PMID: 8572933.
7: Goeger DE, Cheeke PR, Ramsdell HS, Nicholson SS, Buhler DR. Comparison of the toxicities of Senecio jacobaea, Senecio vulgaris and Senecio glabellus in rats. Toxicol Lett. 1983 Jan;15(1):19-23. PubMed PMID: 6836586.
8: 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.
