MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 463346 | Name: Cinmethylin
Featured

Description:

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

Cinmethylin belongs to the cineole family and is a pre-emergence herbicide developed for the control of annual grass weeds.

Chemical Structure

Cinmethylin
Cinmethylin
CAS#87818-31-3

Theoretical Analysis

MedKoo Cat#: 463346

Name: Cinmethylin

CAS#: 87818-31-3

Chemical Formula: C18H26O2

Exact Mass: 274.1933

Molecular Weight: 274.40

Elemental Analysis: C, 78.79; H, 9.55; O, 11.66

Price and Availability

Size Price Availability Quantity
50mg USD 550.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Cinmethylin; Argold; Caswell No. 731G; Cinch; EPA Pesticide Chemical Code 128837;
IUPAC/Chemical Name
(1S,2R,4R)-4-isopropyl-1-methyl-2-((2-methylbenzyl)oxy)-7-oxabicyclo[2.2.1]heptane
InChi Key
QMTNOLKHSWIQBE-FGTMMUONSA-N
InChi Code
InChI=1S/C18H26O2/c1-13(2)18-10-9-17(4,20-18)16(11-18)19-12-15-8-6-5-7-14(15)3/h5-8,13,16H,9-12H2,1-4H3/t16-,17+,18-/m1/s1
SMILES Code
CC([C@]12CC[C@](O1)([C@H](OCc3c(C)cccc3)C2)C)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
>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 274.40 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: Busi R, Dayan FE, Francis I, Goggin D, Lerchl J, Porri A, Powles SB, Sun C, Beckie HJ. Cinmethylin controls multiple herbicide-resistant Lolium rigidum and its wheat selectivity is P450-based. Pest Manag Sci. 2020 Aug;76(8):2601-2608. doi: 10.1002/ps.5798. Epub 2020 Feb 28. PMID: 32077583. 2: Goggin DE, Cawthray GR, Busi R, Porri A, Beckie HJ. Enhanced production of water-soluble cinmethylin metabolites by Lolium rigidum populations with reduced cinmethylin sensitivity. Pest Manag Sci. 2022 Jul;78(7):3173-3182. doi: 10.1002/ps.6947. Epub 2022 May 12. PMID: 35470951; PMCID: PMC9325456. 3: Jung J, Schmölzer K, Schachtschabel D, Speitling M, Nidetzky B. Selective β-Mono-Glycosylation of a C15-Hydroxylated Metabolite of the Agricultural Herbicide Cinmethylin Using Leloir Glycosyltransferases. J Agric Food Chem. 2021 May 19;69(19):5491-5499. doi: 10.1021/acs.jafc.1c01321. Epub 2021 May 11. PMID: 33973475; PMCID: PMC8278484. 4: Ogawa N, Toyoshima S, Sekikawa S, Ishijima M, Katagiri K, Uematsu C, Hirano T, Ootaka A, Suzuki J. Synthesis and herbicidal activity of optically active cinmethylin, its enantiomer, and C3-substituted cinmethylin analogs. J Pestic Sci. 2023 Feb 20;48(1):11-16. doi: 10.1584/jpestics.D22-051. PMID: 36874636; PMCID: PMC9978247. 5: Campe R, Hollenbach E, Kämmerer L, Hendriks J, Höffken HW, Kraus H, Lerchl J, Mietzner T, Tresch S, Witschel M, Hutzler J. A new herbicidal site of action: Cinmethylin binds to acyl-ACP thioesterase and inhibits plant fatty acid biosynthesis. Pestic Biochem Physiol. 2018 Jun;148:116-125. doi: 10.1016/j.pestbp.2018.04.006. Epub 2018 Apr 20. PMID: 29891362. 6: Grossmann K, Hutzler J, Tresch S, Christiansen N, Looser R, Ehrhardt T. On the mode of action of the herbicides cinmethylin and 5-benzyloxymethyl-1, 2-isoxazolines: putative inhibitors of plant tyrosine aminotransferase. Pest Manag Sci. 2012 Mar;68(3):482-92. doi: 10.1002/ps.2319. Epub 2011 Nov 10. PMID: 22076790. 7: Hsu FC, Marxmiller RL, Yang AY. Study of root uptake and xylem translocation of cinmethylin and related compounds in detopped soybean roots using a pressure chamber technique. Plant Physiol. 1990 Aug;93(4):1573-8. doi: 10.1104/pp.93.4.1573. PMID: 16667658; PMCID: PMC1062713. 8: Mendoza SD, Rombola M, Tao Y, Zuend SJ, Götz R, McLaughlin MJ, Reisman SE. Expanding the Chiral Monoterpene Pool: Enantioselective Diels-Alder Reactions of α-Acyloxy Enones. Org Lett. 2022 Jun 3;24(21):3802-3806. doi: 10.1021/acs.orglett.2c01343. Epub 2022 May 20. PMID: 35594569. 9: Johnen P, Zimmermann S, Betz M, Hendriks J, Zimmermann A, Marnet M, De I, Zimmermann G, Kibat C, Cornaciu I, Mariaule V, Pica A, Clavel D, Márquez JA, Witschel M. Inhibition of acyl-ACP thioesterase as site of action of the commercial herbicides cumyluron, oxaziclomefone, bromobutide, methyldymron and tebutam. Pest Manag Sci. 2022 Aug;78(8):3620-3629. doi: 10.1002/ps.7004. Epub 2022 Jun 17. PMID: 35604014. 10: Busi R, Beckie HJ, Bates A, Boyes T, Davey C, Haskins B, Mock S, Newman P, Porri A, Onofri A. Herbicide resistance across the Australian continent. Pest Manag Sci. 2021 Nov;77(11):5139-5148. doi: 10.1002/ps.6554. Epub 2021 Jul 31. PMID: 34260812. 11: Duke SO, Bajsa J, Pan Z. Omics methods for probing the mode of action of natural and synthetic phytotoxins. J Chem Ecol. 2013 Feb;39(2):333-47. doi: 10.1007/s10886-013-0240-0. Epub 2013 Jan 27. PMID: 23355015; PMCID: PMC3589630. 12: Dornbos DL Jr, Spencer GF. Natural products phytotoxicity A bioassay suitable for small quantities of slightly water-soluble compounds. J Chem Ecol. 1990 Feb;16(2):339-52. doi: 10.1007/BF01021769. PMID: 24263494. 13: Romagni JG, Duke SO, Dayan FE. Inhibition of plant asparagine synthetase by monoterpene cineoles. Plant Physiol. 2000 Jun;123(2):725-32. doi: 10.1104/pp.123.2.725. Retraction in: Romagni JG, Duke SO, Dayan FE. Plant Physiol. 2005 Apr;137(4):1487. PMID: 10859202; PMCID: PMC59040. 14: Kibasa V, Mahajan G, Chauhan BS. Seed germination ecology of hood canarygrass (Phalaris paradoxa L.) and herbicide options for its control. Sci Rep. 2022 Sep 9;12(1):15241. doi: 10.1038/s41598-022-19418-8. PMID: 36085300; PMCID: PMC9463434. 15: Einhellig FA, Leather GR. Potentials for exploiting allelopathy to enhance crop production. J Chem Ecol. 1988 Oct;14(10):1829-44. doi: 10.1007/BF01013480. PMID: 24277097. 16: Jung J, Schachtschabel D, Speitling M, Nidetzky B. Controllable Iterative β-Glucosylation from UDP-Glucose by Bacillus cereus Glycosyltransferase GT1: Application for the Synthesis of Disaccharide-Modified Xenobiotics. J Agric Food Chem. 2021 Dec 8;69(48):14630-14642. doi: 10.1021/acs.jafc.1c05788. Epub 2021 Nov 24. PMID: 34817995; PMCID: PMC8662728. 17: Wu J, Ma JJ, Liu B, Huang L, Sang XQ, Zhou LJ. Herbicidal Spectrum, Absorption and Transportation, and Physiological Effect on Bidens pilosa of the Natural Alkaloid Berberine. J Agric Food Chem. 2017 Aug 2;65(30):6100-6113. doi: 10.1021/acs.jafc.7b01259. Epub 2017 Jul 20. PMID: 28700828. 18: Yang X, Guschina IA, Hurst S, Wood S, Langford M, Hawkes T, Harwood JL. The action of herbicides on fatty acid biosynthesis and elongation in barley and cucumber. Pest Manag Sci. 2010 Jul;66(7):794-800. doi: 10.1002/ps.1944. PMID: 20533380. 19: Patnaik GK, Kanungo PK, Moorthy BT, Mahana PK, Adhya TK, Rao VR. Effect of herbicides on nitrogen fixation (C2H2 reduction) associated with rice rhizosphere. Chemosphere. 1995 Jan;30(2):339-43. doi: 10.1016/0045-6535(94)00401-f. PMID: 7874477.