MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 598597 | Name: Leptospermone

Description:

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

Leptospermone is an essential oil of Leptospermum scoparium (manuka oil).

Chemical Structure

Leptospermone
Leptospermone
CAS#567-75-9

Theoretical Analysis

MedKoo Cat#: 598597

Name: Leptospermone

CAS#: 567-75-9

Chemical Formula: C15H22O4

Exact Mass: 266.1518

Molecular Weight: 266.33

Elemental Analysis: C, 67.65; H, 8.33; O, 24.03

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
Leptospermone;
IUPAC/Chemical Name
2,2,4,4-tetramethyl-6-(3-methylbutanoyl)cyclohexane-1,3,5-trione
InChi Key
YDWYMAHAWHBPPT-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H22O4/c1-8(2)7-9(16)10-11(17)14(3,4)13(19)15(5,6)12(10)18/h8,10H,7H2,1-6H3
SMILES Code
O=C1C(C)(C)C(C(C)(C)C(C1C(CC(C)C)=O)=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 266.33 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: Owens DK, Nanayakkara NP, Dayan FE. In planta mechanism of action of leptospermone: impact of its physico-chemical properties on uptake, translocation, and metabolism. J Chem Ecol. 2013 Feb;39(2):262-70. doi: 10.1007/s10886-013-0237-8. Epub 2013 Jan 13. PubMed PMID: 23314892. 2: Romdhane S, Devers-Lamrani M, Barthelmebs L, Calvayrac C, Bertrand C, Cooper JF, Dayan FE, Martin-Laurent F. Ecotoxicological Impact of the Bioherbicide Leptospermone on the Microbial Community of Two Arable Soils. Front Microbiol. 2016 May 24;7:775. doi: 10.3389/fmicb.2016.00775. eCollection 2016. PubMed PMID: 27252691; PubMed Central PMCID: PMC4877392. 3: Trivella A, Stawinoga M, Dayan FE, Cantrell CL, Mazellier P, Richard C. Photolysis of natural β-triketonic herbicides in water. Water Res. 2015 Jul 1;78:28-36. doi: 10.1016/j.watres.2015.03.026. Epub 2015 Apr 9. PubMed PMID: 25898250. 4: BRIGGS LH, HASSALL CH, TAYLOR WI. A synthesis of leptospermone. J Chem Soc. 1948 Mar;174:383. PubMed PMID: 18914117. 5: Jeong EY, Kim MG, Lee HS. Acaricidal activity of triketone analogues derived from Leptospermum scoparium oil against house-dust and stored-food mites. Pest Manag Sci. 2009 Mar;65(3):327-31. doi: 10.1002/ps.1684. PubMed PMID: 19051215. 6: Patil C, Calvayrac C, Zhou Y, Romdhane S, Salvia MV, Cooper JF, Dayan FE, Bertrand C. Environmental Metabolic Footprinting: A novel application to study the impact of a natural and a synthetic β-triketone herbicide in soil. Sci Total Environ. 2016 Oct 1;566-567:552-558. doi: 10.1016/j.scitotenv.2016.05.071. Epub 2016 May 27. PubMed PMID: 27236620. 7: Romdhane S, Devers-Lamrani M, Martin-Laurent F, Jrad AB, Raviglione D, Salvia MV, Besse-Hoggan P, Dayan FE, Bertrand C, Barthelmebs L. Evidence for photolytic and microbial degradation processes in the dissipation of leptospermone, a natural β-triketone herbicide. Environ Sci Pollut Res Int. 2017 Jul 17. doi: 10.1007/s11356-017-9728-4. [Epub ahead of print] PubMed PMID: 28718021. 8: Dayan FE, Duke SO, Sauldubois A, Singh N, McCurdy C, Cantrell C. p-Hydroxyphenylpyruvate dioxygenase is a herbicidal target site for beta-triketones from Leptospermum scoparium. Phytochemistry. 2007 Jul;68(14):2004-14. Epub 2007 Mar 26. PubMed PMID: 17368492. 9: Reichling J, Koch C, Stahl-Biskup E, Sojka C, Schnitzler P. Virucidal activity of a beta-triketone-rich essential oil of Leptospermum scoparium (manuka oil) against HSV-1 and HSV-2 in cell culture. Planta Med. 2005 Dec;71(12):1123-7. PubMed PMID: 16395648. 10: Rocaboy-Faquet E, Noguer T, Romdhane S, Bertrand C, Dayan FE, Barthelmebs L. Novel bacterial bioassay for a high-throughput screening of 4-hydroxyphenylpyruvate dioxygenase inhibitors. Appl Microbiol Biotechnol. 2014 Aug;98(16):7243-52. doi: 10.1007/s00253-014-5793-5. Epub 2014 May 13. PubMed PMID: 24816780. 11: Romdhane S, Devers-Lamrani M, Martin-Laurent F, Calvayrac C, Rocaboy-Faquet E, Riboul D, Cooper JF, Barthelmebs L. Isolation and characterization of Bradyrhizobium sp. SR1 degrading two β-triketone herbicides. Environ Sci Pollut Res Int. 2016 Mar;23(5):4138-48. doi: 10.1007/s11356-015-4544-1. Epub 2015 Apr 24. PubMed PMID: 25903192. 12: Mustafa K, Perry NB, Weavers RT. 2-Hydroxyflavanones from Leptospermum polygalifolium subsp. polygalifolium Equilibrating sets of hemiacetal isomers. Phytochemistry. 2003 Dec;64(7):1285-93. PubMed PMID: 14599527. 13: van Klink JW, Brophy JJ, Perry NB, Weavers RT. beta-triketones from myrtaceae: isoleptospermone from leptospermum scoparium and papuanone from corymbia dallachiana . J Nat Prod. 1999 Mar;62(3):487-9. PubMed PMID: 10096865. 14: Agampodi SB, Peacock SJ, Thevanesam V, Nugegoda DB, Smythe L, Thaipadungpanit J, Craig SB, Burns MA, Dohnt M, Boonsilp S, Senaratne T, Kumara A, Palihawadana P, Perera S, Vinetz JM. Leptospirosis outbreak in Sri Lanka in 2008: lessons for assessing the global burden of disease. Am J Trop Med Hyg. 2011 Sep;85(3):471-8. doi: 10.4269/ajtmh.2011.11-0276. Erratum in: Am J Trop Med Hyg. 2011 Oct;85(4):790. PubMed PMID: 21896807; PubMed Central PMCID: PMC3163869. 15: Schnitzler P, Wiesenhofer K, Reichling J. Comparative study on the cytotoxicity of different Myrtaceae essential oils on cultured vero and RC-37 cells. Pharmazie. 2008 Nov;63(11):830-5. PubMed PMID: 19069246. 16: Dayan FE, Singh N, McCurdy CR, Godfrey CA, Larsen L, Weavers RT, Van Klink JW, Perry NB. Beta-triketone inhibitors of plant p-hydroxyphenylpyruvate dioxygenase: modeling and comparative molecular field analysis of their interactions. J Agric Food Chem. 2009 Jun 24;57(12):5194-200. doi: 10.1021/jf9005593. PubMed PMID: 19435355. 17: Lock EA. From Weed Killer to Wonder Drug. Adv Exp Med Biol. 2017;959:175-185. doi: 10.1007/978-3-319-55780-9_16. Review. PubMed PMID: 28755195. 18: Park CG, Jang M, Shin E, Kim J. Myrtaceae Plant Essential Oils and their β-Triketone Components as Insecticides against Drosophila suzukii. Molecules. 2017 Jun 24;22(7). pii: E1050. doi: 10.3390/molecules22071050. PubMed PMID: 28672824. 19: Alvarez Costa A, Naspi CV, Lucia A, Masuh HM. Repellent and Larvicidal Activity of the Essential Oil From Eucalyptus nitens Against Aedes aegypti and Aedes albopictus (Diptera: Culicidae). J Med Entomol. 2017 May 1;54(3):670-676. doi: 10.1093/jme/tjw222. PubMed PMID: 28399283. 20: Fratini F, Mancini S, Turchi B, Friscia E, Pistelli L, Giusti G, Cerri D. A novel interpretation of the Fractional Inhibitory Concentration Index: The case Origanum vulgare L. and Leptospermum scoparium J. R. et G. Forst essential oils against Staphylococcus aureus strains. Microbiol Res. 2017 Jan;195:11-17. doi: 10.1016/j.micres.2016.11.005. Epub 2016 Nov 18. PubMed PMID: 28024521.