MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 462662 | Name: Thuringiensin

Description:

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

Thuringiensin, also known as β-exotoxin, is a thermostable secondary metabolite secreted by Bacillus thuringiensis. It has insecticidal activity against a wide range of insects, including species belonging to the orders Diptera, Coleoptera, Lepidoptera, Hymenoptera, Orthoptera, and Isoptera, and several nematode species.

Chemical Structure

Thuringiensin
Thuringiensin
CAS#23526-02-5

Theoretical Analysis

MedKoo Cat#: 462662

Name: Thuringiensin

CAS#: 23526-02-5

Chemical Formula: C22H32N5O19P

Exact Mass: 701.1429

Molecular Weight: 701.49

Elemental Analysis: C, 37.67; H, 4.60; N, 9.98; O, 43.33; P, 4.42

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.
Bulk Inquiry
Related CAS #
No Data
Synonym
NSC197177; NSC 197177; NSC-197177;
IUPAC/Chemical Name
(2R,3S,4S,5S)-2-(((2R,3R,4R,5S,6R)-5-(((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,5-dihydroxy-4-(phosphonooxy)hexanedioic acid
InChi Key
OTLLEIBWKHEHGU-TUNUFRSWSA-N
InChi Code
InChI=1S/C22H32N5O19P/c23-17-7-18(25-3-24-17)27(4-26-7)19-10(31)8(29)6(43-19)2-42-14-5(1-28)44-22(11(32)9(14)30)45-16(21(37)38)12(33)15(13(34)20(35)36)46-47(39,40)41/h3-6,8-16,19,22,28-34H,1-2H2,(H,35,36)(H,37,38)(H2,23,24,25)(H2,39,40,41)/t5-,6-,8-,9-,10-,11-,12-,13+,14-,15+,16-,19-,22-/m1/s1
SMILES Code
O=C(O)[C@H](O[C@@H]1[C@H](O)[C@@H](O)[C@H](OC[C@H]2O[C@@H](N3C=NC4=C(N)N=CN=C34)[C@H](O)[C@@H]2O)[C@@H](CO)O1)[C@H](O)[C@H](OP(O)(O)=O)[C@H](O)C(O)=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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 701.49 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: Liu X, Ruan L, Peng D, Li L, Sun M, Yu Z. Thuringiensin: a thermostable secondary metabolite from Bacillus thuringiensis with insecticidal activity against a wide range of insects. Toxins (Basel). 2014 Jul 25;6(8):2229-38. doi: 10.3390/toxins6082229. PMID: 25068925; PMCID: PMC4147579. 2: Tsai SF, Yang C, Wang SC, Wang JS, Hwang JS, Ho SP. Effect of thuringiensin on adenylate cyclase in rat cerebral cortex. Toxicol Appl Pharmacol. 2004 Jan 1;194(1):34-40. doi: 10.1016/j.taap.2003.08.015. PMID: 14728977. 3: Tsai SF, Yang C, Liu BL, Hwang JS, Ho SP. Role of oxidative stress in thuringiensin-induced pulmonary toxicity. Toxicol Appl Pharmacol. 2006 Oct 15;216(2):347-53. doi: 10.1016/j.taap.2006.05.013. Epub 2006 May 24. PMID: 16839580. 4: Tsai SF, Liu BL, Liao JW, Wang JS, Hwang JS, Wang SC, Tzeng YM, Ho SP. Pulmonary toxicity of thuringiensin administered intratracheally in Sprague- Dawley rats. Toxicology. 2003 Apr 22;186(3):205-16. doi: 10.1016/s0300-483x(02)00744-8. PMID: 12628313. 5: Tzeng YM, Young YH. Penicillin-G enhanced production of thuringiensin by Bacillus thuringiensis sp. darmstadiensis. Biotechnol Prog. 1995 Mar- Apr;11(2):231-4. doi: 10.1021/bp00032a018. PMID: 7766105. 6: Zhou J, Xu Z, Chen S. Simulation and prediction of the thuringiensin abiotic degradation processes in aqueous solution by a radius basis function neural network model. Chemosphere. 2013 Apr;91(4):442-7. doi: 10.1016/j.chemosphere.2012.11.062. Epub 2012 Dec 27. PMID: 23273880. 7: Zhi W, Shouwen C, Lifang R, Ming S, Ziniu Y. A fundamental regulatory role of formate on thuringiensin production by resting cell of Bacillus thuringiensis YBT-032. Bioprocess Biosyst Eng. 2007 Jul;30(4):225-9. doi: 10.1007/s00449-007-0118-z. PMID: 17387519. 8: Liu XY, Ruan LF, Hu ZF, Peng DH, Cao SY, Yu ZN, Liu Y, Zheng JS, Sun M. Genome-wide screening reveals the genetic determinants of an antibiotic insecticide in Bacillus thuringiensis. J Biol Chem. 2010 Dec 10;285(50):39191-200. doi: 10.1074/jbc.M110.148387. Epub 2010 Sep 23. PMID: 20864531; PMCID: PMC2998090. 9: Wang Z, Chen S, Sun M, Yu Z. A fundamental dual regulatory role of citrate on the biosyntheses of thuringiensin and poly-beta-hydroxybutyrate in Bacillus thuringiensis YBT-032. Biotechnol Lett. 2007 May;29(5):779-84. doi: 10.1007/s10529-006-9302-5. Epub 2007 Feb 6. PMID: 17279445. 10: de Rijk TC, van Dam RC, Zomer P, Boers EA, de Waard P, Mol HG. Development and validation of a confirmative LC-MS/MS method for the determination of ß-exotoxin thuringiensin in plant protection products and selected greenhouse crops. Anal Bioanal Chem. 2013 Feb;405(5):1631-9. doi: 10.1007/s00216-012-6591-5. Epub 2012 Dec 5. PMID: 23208288. 11: Guo C, Hu Z, Liu X, Yu Z, Ruan L, Sun M, Yu Z. [Differential expression protein between the thuringiensin-yield Bacillus thuringiensis strain CT-43 and its mutants]. Wei Sheng Wu Xue Bao. 2008 Jul;48(7):970-4. Chinese. PMID: 18837379. 12: Wu WT, Hsu YL, Ko YF, Yao LL. Effect of shear stress on cultivation of Bacillus thuringiensis for thuringiensin production. Appl Microbiol Biotechnol. 2002 Feb;58(2):175-7. doi: 10.1007/s00253-001-0827-1. PMID: 11876409. 13: Tzeng YM, Tsun HY, Chang YN. Recovery of thuringiensin with cetylpyridinium chloride using micellar-enhanced ultrafiltration process. Biotechnol Prog. 1999 May;15(3):580-6. doi: 10.1021/bp990053o. PMID: 10356280. 14: Liu CM, Tzeng YM. Quantitative analysis of thuringiensin by high-performance liquid chromatography using adenosine monophosphate as an internal standard. J Chromatogr Sci. 1998 Jul;36(7):340-4. doi: 10.1093/chromsci/36.7.340. PMID: 9679301. 15: Carlberg G, Tikkanen L, Abdel-Hameed AH. Safety testing of Bacillus thuringiensis preparations, including thuringiensin, using the Salmonella assay. J Invertebr Pathol. 1995 Jul;66(1):68-71. doi: 10.1006/jipa.1995.1062. PMID: 7658050. 16: Jong JZ, Hsiun DY, Wu WT, Tzeng YM. Fed-batch culture of Bacillus thuringiensis for thuringiensin production in a tower type bioreactor. Biotechnol Bioeng. 1995 Nov 5;48(3):207-13. doi: 10.1002/bit.260480307. PMID: 18623480. 17: Tzeng YM, Young YH. Production of thuringiensin from Bacillus thuringiensis using a net-draft-tube, modified airlift reactor. World J Microbiol Biotechnol. 1996 Jan;12(1):32-7. doi: 10.1007/BF00327796. PMID: 24415084. 18: Noel GR. Evaluation of Thuringiensin for Control of Heterodera glycines on Soybean. J Nematol. 1990 Oct;22(4S):763-6. PMID: 19287793; PMCID: PMC2619120. 19: He J, Wang J, Yin W, Shao X, Zheng H, Li M, Zhao Y, Sun M, Wang S, Yu Z. Complete genome sequence of Bacillus thuringiensis subsp. chinensis strain CT-43. J Bacteriol. 2011 Jul;193(13):3407-8. doi: 10.1128/JB.05085-11. Epub 2011 May 6. PMID: 21551307; PMCID: PMC3133296. 20: Zheng Z, Zheng J, Zhang Z, Peng D, Sun M. Nematicidal spore-forming Bacilli share similar virulence factors and mechanisms. Sci Rep. 2016 Aug 19;6:31341. doi: 10.1038/srep31341. PMID: 27539267; PMCID: PMC4990965.

View History

Thujone

Thujone