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Chemical Structure| 496-16-2 Chemical Structure| 496-16-2
Chemical Structure| 496-16-2

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Coumaran (2,3-Dihydrobenzofuran) is an acetylcholinesterase (AChE) inhibitor isolated from leaves of L. camara. Coumaran can be used as a biopesticide.

Synonyms: 2,3-Dihydrobenzofuran

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Product Citations

Product Citations

Fryer, Emily ; Guha, Sujay ; Rogel-Hernandez, Lucero E ; Logan-Garbisch, Theresa ; Farah, Hodan ; Rezaei, Ehsan , et al.

Abstract: Throughout history, humans have relied on plants as a source of medication, flavoring, and food. Plants synthesize large chemical libraries and release many of these compounds into the rhizosphere and atmosphere where they affect animal and microbe behavior. To survive, nematodes must have evolved the sensory capacity to distinguish plant-made small molecules (SMs) that are harmful and must be avoided from those that are beneficial and should be sought. This ability to classify chemical cues as a function of their value is fundamental to olfaction, and represents a capacity shared by many animals, including humans. Here, we present an efficient platform based on multi-well plates, liquid handling instrumentation, low-cost optical scanners, and bespoke software that can efficiently determine the chemotaxis valence of single SMs in the model nematode, Caenorhabditis elegans. Using this integrated hardware-wetware-software platform, we screened 90 plant SMs and identified 37 that attracted or repelled wild-type animals, but had no effect on mutants defective in chemosensory transduction. Genetic dissection indicates that for at least 10 of these SMs, response valence emerges from the integration of opposing signals, arguing that olfactory valence is often determined by integrating chemosensory signals over multiple lines of information. This study establishes that C. elegans is an effective discovery engine for determining chemotaxis valence and for identifying natural products detected by the chemosensory nervous system.

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Product Details of Coumaran

CAS No. :496-16-2
Formula : C8H8O
M.W : 120.15
SMILES Code : C1=CC=CC2=C1CCO2
Synonyms :
2,3-Dihydrobenzofuran
MDL No. :MFCD00005855
InChI Key :HBEDSQVIWPRPAY-UHFFFAOYSA-N
Pubchem ID :10329

Safety of Coumaran

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of Coumaran

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 496-16-2 ]
  • Downstream synthetic route of [ 496-16-2 ]

[ 496-16-2 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 496-16-2 ]
  • [ 76429-69-1 ]
References: [1] Journal of Organic Chemistry, 2017, vol. 82, # 14, p. 7529 - 7537.
[2] Synlett, 2005, # 18, p. 2837 - 2842.
[3] Patent: WO2007/27917, 2007, A2, . Location in patent: Page/Page column 26.
  • 2
  • [ 496-16-2 ]
  • [ 42933-43-7 ]
References: [1] ACS Catalysis, 2016, vol. 6, # 12, p. 8162 - 8165.
[2] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 21, p. 6430 - 6446.
[3] Patent: EP2532665, 2012, A1, .
[4] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 13, p. 3821 - 3830.
[5] Journal of Medicinal Chemistry, 2014, vol. 57, # 13, p. 5579 - 5601.
  • 3
  • [ 496-16-2 ]
  • [ 42933-43-7 ]
  • [ 13414-56-7 ]
References: [1] Chemistry - A European Journal, 2017, vol. 23, # 3, p. 563 - 567.
  • 4
  • [ 496-16-2 ]
  • [ 869885-60-9 ]
References: [1] Patent: US2008/227744, 2008, A1, .
 

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