Jacobine

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

MedKoo CAT#: 596089

CAS#: 6870-67-3

Description: Jacobine is a Pyrrolizidine Alkaloid.


Chemical Structure

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Jacobine
CAS# 6870-67-3

Theoretical Analysis

MedKoo Cat#: 596089
Name: Jacobine
CAS#: 6870-67-3
Chemical Formula: C18H25NO6
Exact Mass: 351.1682
Molecular Weight: 351.39
Elemental Analysis: C, 61.52; H, 7.17; N, 3.99; O, 27.32

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.

Request quote for custom synthesis

Synonym: Jacobine;

IUPAC/Chemical Name: (5'R,6'R,9a1'R,14a'R)-6'-hydroxy-3,5',6'-trimethyl-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: IAPHXJRHXBQDQJ-QXONMQPNSA-N

InChi Code: InChI=1S/C18H25NO6/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/h4,10-11,13-14,22H,5-9H2,1-3H3/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)(O4)C4C)=O)CCN1CC=C2COC3=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 351.39 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: Rozhon W, Kammermeier L, Schramm S, Towfique N, Adebimpe Adedeji N, Adesola Ajayi S, Poppenberger B. Quantification of the Pyrrolizidine Alkaloid Jacobine in Crassocephalum crepidioides by Cation Exchange High-Performance Liquid Chromatography. Phytochem Anal. 2018 Jan;29(1):48-58. doi: 10.1002/pca.2713. Epub 2017 Aug 24. PubMed PMID: 28836707.

2: Liu X, Klinkhamer PGL, Vrieling K. The effect of structurally related metabolites on insect herbivores: A case study on pyrrolizidine alkaloids and western flower thrips. Phytochemistry. 2017 Jun;138:93-103. doi: 10.1016/j.phytochem.2017.02.027. Epub 2017 Mar 6. PubMed PMID: 28267991.

3: Bovee TF, Helsdingen RJ, Hoogenboom RL, de Nijs MW, Liu X, Vrieling K, Klinkhamer PG, Peijnenburg AA, Mulder PP. Are effects of common ragwort in the Ames test caused by pyrrolizidine alkaloids? Mutat Res. 2015 Aug;778:1-10. doi: 10.1016/j.mrfmmm.2015.05.006. Epub 2015 May 15. PubMed PMID: 26021695.

4: Wei X, Vrieling K, Mulder PP, Klinkhamer PG. Testing the generalist-specialist dilemma: the role of pyrrolizidine alkaloids in resistance to invertebrate herbivores in Jacobaea species. J Chem Ecol. 2015 Feb;41(2):159-67. doi: 10.1007/s10886-015-0551-4. Epub 2015 Feb 11. PubMed PMID: 25666592; PubMed Central PMCID: PMC4351440.

5: Nuringtyas TR, Verpoorte R, Klinkhamer PG, van Oers MM, Leiss KA. Toxicity of pyrrolizidine alkaloids to Spodoptera exigua using insect cell lines and injection bioassays. J Chem Ecol. 2014 Jun;40(6):609-16. doi: 10.1007/s10886-014-0459-4. Epub 2014 Jul 1. PubMed PMID: 24981118.

6: Oplatowska M, Elliott CT, Huet AC, McCarthy M, Mulder PP, von Holst C, Delahaut P, Van Egmond HP, Campbell K. Development and validation of a rapid multiplex ELISA for pyrrolizidine alkaloids and their N-oxides in honey and feed. Anal Bioanal Chem. 2014 Jan;406(3):757-70. doi: 10.1007/s00216-013-7488-7. Epub 2013 Dec 11. PubMed PMID: 24327075.

7: Cheng D, van der Meijden E, Mulder PP, Vrieling K, Klinkhamer PG. Pyrrolizidine alkaloid composition influences cinnabar moth oviposition preferences in Jacobaea hybrids. J Chem Ecol. 2013 Mar;39(3):430-7. doi: 10.1007/s10886-013-0257-4. Epub 2013 Feb 24. PubMed PMID: 23435642.

8: Kostenko O, Mulder PP, Bezemer TM. Effects of root herbivory on pyrrolizidine alkaloid content and aboveground plant-herbivore-parasitoid interactions in Jacobaea vulgaris. J Chem Ecol. 2013 Jan;39(1):109-19. doi: 10.1007/s10886-012-0234-3. Epub 2013 Jan 10. PubMed PMID: 23306864.

9: Jacobine AM, Puchlopek AL, Zercher CK, Briggs JB, Jasinski JP, Butcher RJ. Tandem chain extension-Mannich reaction: an approach to β-proline derivatives. Tetrahedron. 2012 Sep 23;68(38):7799-7805. Epub 2012 Jul 17. PubMed PMID: 23139434; PubMed Central PMCID: PMC3489501.

10: Jacobine AM, Mazzone JR, Slack RD, Tripathi AK, Sullivan DJ, Posner GH. Malaria-infected mice live until at least day 30 after a new artemisinin-derived thioacetal thiocarbonate combined with mefloquine are administered together in a single, low, oral dose. J Med Chem. 2012 Sep 13;55(17):7892-9. doi: 10.1021/jm3009986. Epub 2012 Aug 27. PubMed PMID: 22891714; PubMed Central PMCID: PMC3460521.

11: 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.

12: 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.

13: Jacobine AM, Posner GH. Three-component, one-flask synthesis of rhodanines (thiazolidinones). J Org Chem. 2011 Oct 7;76(19):8121-5. doi: 10.1021/jo201561t. Epub 2011 Aug 31. PubMed PMID: 21853986; PubMed Central PMCID: PMC3184363.

14: 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.

15: 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.

16: Kempf M, Wittig M, Reinhard A, von der Ohe K, Blacquière T, Raezke KP, Michel R, Schreier P, Beuerle T. Pyrrolizidine alkaloids in honey: comparison of analytical methods. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2011 Mar;28(3):332-47. doi: 10.1080/19440049.2010.521772. Epub 2010 Nov 12. PubMed PMID: 21082464.

17: 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.

18: Jacobine AM, Lin W, Walls B, Zercher CK. Formation of gamma-lactones through CAN-mediated oxidative cleavage of hemiketals. J Org Chem. 2008 Sep 19;73(18):7409-12. doi: 10.1021/jo801258h. Epub 2008 Aug 12. PubMed PMID: 18693768.

19: 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.

20: 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.