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MedKoo Cat#: 461574 | Name: Isoline

Description:

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

Isoline is a pyrrolizidine alkaloid that is isolated from the traditional Chinese medicine Ligularia duciformis.

Chemical Structure

Isoline
Isoline
CAS#30000-36-3

Theoretical Analysis

MedKoo Cat#: 461574

Name: Isoline

CAS#: 30000-36-3

Chemical Formula: C20H29NO7

Exact Mass: 395.1944

Molecular Weight: 395.45

Elemental Analysis: C, 60.75; H, 7.39; N, 3.54; O, 28.32

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Isoline; Ruwenine;
IUPAC/Chemical Name
(3R,5R,6S,9a1R,14aR)-3-ethyl-3-hydroxy-5,6-dimethyl-2,7-dioxo-2,3,4,5,6,7,9,9a1,11,13,14,14a-dodecahydro-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizin-6-yl acetate
InChi Key
IYLGZMTXKJYONK-ACLXAEORSA-N
InChi Code
InChI=1S/C20H29NO7/c1-5-20(25)10-12(2)19(4,28-13(3)22)17(23)26-11-14-6-8-21-9-7-15(16(14)21)27-18(20)24/h6,12,15-16,25H,5,7-11H2,1-4H3/t12-,15-,16-,19+,20-/m1/s1
SMILES Code
O=C(O[C@]1([H])CCN2[C@]1([H])C(CO3)=CC2)[C@@](O)(CC)C[C@@H](C)[C@](C)(OC(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
>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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 395.45 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
1: Chen Y, Ji L, Xiong A, Yang L, Wang Z. Involvement of intracellular glutathione in regulating isoline-induced cytotoxicity in human normal liver L-02 cells. Toxicol Ind Health. 2013 Jul;29(6):567-75. doi: 10.1177/0748233712442707. Epub 2012 Apr 2. PubMed PMID: 22474030. 2: Wang ZY, Kang H, Ji LL, Yang YQ, Liu TY, Cao ZW, Morahan G, Wang ZT. Proteomic characterization of the possible molecular targets of pyrrolizidine alkaloid isoline-induced hepatotoxicity. Environ Toxicol Pharmacol. 2012 Sep;34(2):608-617. doi: 10.1016/j.etap.2012.06.013. Epub 2012 Jul 6. PubMed PMID: 22885678. 3: Holderbaum DF, Cuhra M, Wickson F, Orth AI, Nodari RO, Bøhn T. Chronic Responses of Daphnia magna Under Dietary Exposure to Leaves of a Transgenic (Event MON810) Bt-Maize Hybrid and its Conventional Near-Isoline. J Toxicol Environ Health A. 2015;78(15):993-1007. doi: 10.1080/15287394.2015.1037877. PubMed PMID: 26262442; PubMed Central PMCID: PMC4566889. 4: Liu TY, Chen Y, Wang ZY, Ji LL, Wang ZT. Pyrrolizidine alkaloid isoline-induced oxidative injury in various mouse tissues. Exp Toxicol Pathol. 2010 May;62(3):251-7. doi: 10.1016/j.etp.2009.04.008. Epub 2009 Jun 21. PubMed PMID: 19540740. 5: Liang Q, Sheng Y, Jiang P, Ji L, Xia Y, Min Y, Wang Z. The gender-dependent difference of liver GSH antioxidant system in mice and its influence on isoline-induced liver injury. Toxicology. 2011 Feb 4;280(1-2):61-9. doi: 10.1016/j.tox.2010.11.010. Epub 2010 Nov 30. PubMed PMID: 21126554. 6: Liang QN, Sheng YC, Jiang P, Ji LL, Xia YY, Min Y, Wang ZT. The difference of glutathione antioxidant system in newly weaned and young mice liver and its involvement in isoline-induced hepatotoxicity. Arch Toxicol. 2011 Oct;85(10):1267-79. doi: 10.1007/s00204-011-0664-7. Epub 2011 Feb 16. PubMed PMID: 21327617. 7: Tang J, Akao T, Nakamura N, Wang ZT, Takagawa K, Sasahara M, Hattori M. In vitro metabolism of isoline, a pyrrolizidine alkaloid from Ligularia duciformis, by rodent liver microsomal esterase and enhanced hepatotoxicity by esterase inhibitors. Drug Metab Dispos. 2007 Oct;35(10):1832-9. Epub 2007 Jul 16. PubMed PMID: 17639025. 8: Bortolotto OC, Bueno AF, Stopa YK, Silva GV, Queiroz AP. Development of Dichelops melacanthus and its egg parasitoid Telenomus podisi reared on Bt-soybean MON 87701 x MON 89788 and its near conventional isoline under different temperatures. An Acad Bras Cienc. 2016 May 31;88(2):1023-34. doi: 10.1590/0001-3765201620150257. PubMed PMID: 27254446. 9: McNaughton J, Roberts M, Smith B, Rice D, Hinds M, Schmidt J, Locke M, Brink K, Bryant A, Rood T, Layton R, Lamb I, Delaney B. Comparison of broiler performance when fed diets containing event DP-356Ø43-5 (Optimum GAT), nontransgenic near-isoline control, or commercial reference soybean meal, hulls, and oil. Poult Sci. 2007 Dec;86(12):2569-81. PubMed PMID: 18029803. 10: Tang J, Zhang M, Wang ZT, Akao T, Nakamura N, Hattori M. Simultaneous determination of isoline and its two major metabolites using high-performance liquid chromatography. J Anal Toxicol. 2004 Jan-Feb;28(1):11-5. PubMed PMID: 14987418. 11: Miura M, Obata K, Taniguchi K, Yoshioka H. Improved Accuracy of the Asymmetric Second-Order Vegetation Isoline Equation over the RED-NIR Reflectance Space. Sensors (Basel). 2017 Feb 24;17(3). pii: E450. doi: 10.3390/s17030450. PubMed PMID: 28245566; PubMed Central PMCID: PMC5375736. 12: Hannula SE, Boschker HT, de Boer W, van Veen JA. 13C pulse-labeling assessment of the community structure of active fungi in the rhizosphere of a genetically starch-modified potato (Solanum tuberosum) cultivar and its parental isoline. New Phytol. 2012 May;194(3):784-99. doi: 10.1111/j.1469-8137.2012.04089.x. Epub 2012 Mar 13. PubMed PMID: 22413848. 13: Edmonds WR. Isoline method of portraying atmospheric attenuation of laser radiation. Appl Opt. 1975 Jun 1;14(6):1263-5. doi: 10.1364/AO.14.001263. PubMed PMID: 20154814. 14: Bertaux N, Frauel Y, Réfrégier P, Javidi B. Speckle removal using a maximum-likelihood technique with isoline gray-level regularization. J Opt Soc Am A Opt Image Sci Vis. 2004 Dec;21(12):2283-91. PubMed PMID: 15603063. 15: Edmonds WR. Isoline approach to portraying atmospheric turbulence induced laser beam spread. Appl Opt. 1977 Jun 1;16(6):1606-8. doi: 10.1364/AO.16.001606. PubMed PMID: 20168761. 16: Susag L, Parvez M, Mathenge S, Benn MH. Structure revision of isoline (ruwenine), bisline and isolinecic acid. Phytochemistry. 2000 Aug;54(8):933-5. PubMed PMID: 11014292. 17: Hoheisel GA, Fleischer SJ. Coccinellids, aphids, and pollen in diversified vegetable fields with transgenic and isoline cultivars. J Insect Sci. 2007;7:61. doi: 10.1673/031.007.6101. PubMed PMID: 20307238; PubMed Central PMCID: PMC2999459. 18: Zukoff SN, Bailey WC, Ellersieck MR, Hibbard BE. Western corn rootworm larval movement in SmartStax seed blend scenarios. J Econ Entomol. 2012 Aug;105(4):1248-60. PubMed PMID: 22928304. 19: Coucourakis ED, Gordon-Gray CG, Whiteley CG. The senecio alkaloids. The structure and absolute configuration of isoline. J Chem Soc Perkin 1. 1972;18:2339-43. PubMed PMID: 4674456. 20: McNaughton J, Roberts M, Smith B, Rice D, Hinds M, Sanders C, Layton R, Lamb I, Delaney B. Comparison of broiler performance when fed diets containing event DP-3O5423-1, nontransgenic near-isoline control, or commercial reference soybean meal, hulls, and oil. Poult Sci. 2008 Dec;87(12):2549-61. doi: 10.3382/ps.2007-00467. PubMed PMID: 19038811.

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TUL01143

TUL01143

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