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D5765 Aldrich

Denatonium benzoate

≥98%

Synonym: N,N-Diethyl-N-[(2,6-dimethylphenyl­carbamoyl)­methyl]­benzyl­ammonium benzoate, Benzyldiethyl(2,6-xylyl­carbamoyl­methyl)­ammonium benzoate, THS 839

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Properties

Related Categories Building Blocks, Chemical Synthesis, Nitrogen Compounds, Organic Building Blocks, Protected Amines More...
assay   ≥98%
mp   164-168 °C(lit.)

Description

Packaging

1, 5, 10 g in poly bottle

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
WGK Germany 
2
RTECS 
BO6650000

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Peer-Reviewed Papers

References

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The bitter taste receptor (TAS2R) agonists denatonium and chloroquine display distinct patterns of relaxation of the guinea pig trachea. Pulkkinen V, Manson ML, Säfholm J, et al. Am. J. Physiol. Lung Cell. Mol. Physiol. 303(11), L956-66, (2012)

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Characterization of ligands for fish taste receptors. Oike H, Nagai T, Furuyama A, et al. J. Neurosci. 27(21), 5584-92, (2007)

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The taste transduction channel TRPM5 is a locus for bitter-sweet taste interactions. Talavera K, Yasumatsu K, Yoshida R, et al. FASEB J. 22(5), 1343-55, (2008)

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The human bitter taste receptor TAS2R10 is tailored to accommodate numerous diverse ligands. Born S, Levit A, Niv MY, et al. J. Neurosci. 33(1), 201-13, (2013)

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Trpm5 null mice respond to bitter, sweet, and umami compounds. Damak S, Rong M, Yasumatsu K, et al. Chem. Senses 31(3), 253-64, (2006)

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A non-invasive method for ending thumb- and fingersucking habits. Kozlowski JT J. Clin. Orthod. 41(10), 636, (2007)

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Broad tuning of the human bitter taste receptor hTAS2R46 to various sesquiterpene lactones, clerodane and labdane diterpenoids, strychnine, and denatonium. Brockhoff A, Behrens M, Massarotti A, et al. J. Agric. Food Chem. 55(15), 6236-43, (2007)

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Nasal chemosensory cells use bitter taste signaling to detect irritants and bacterial signals. Tizzano M, Gulbransen BD, Vandenbeuch A, et al. Proc. Natl. Acad. Sci. U. S. A. 107(7), 3210-5, (2010)

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Denatonium benzoate: review of efficacy and safety. Klein-Schwartz W Vet. Hum. Toxicol. 33(6), 545-7, (1991)

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Bitter stimuli induce Ca2+ signaling and CCK release in enteroendocrine STC-1 cells: role of L-type voltage-sensitive Ca2+ channels. Chen MC, Wu SV, Reeve JR, et al. Am. J. Physiol. Cell Physiol. 291(4), C726-39, (2006)

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Denatonium benzoate as a deterrent to ingestion of toxic substances: toxicity and efficacy. Hansen SR, Janssen C, and Beasley VR Vet. Hum. Toxicol. 35(3), 234-6, (1993)

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Predators' toxin burdens influence their strategic decisions to eat toxic prey. Skelhorn J and Rowe C Curr. Biol. 17(17), 1479-83, (2007)

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Intragastric infusion of denatonium conditions flavor aversions and delays gastric emptying in rodents. Glendinning JI, Yiin YM, Ackroff K, et al. Physiol. Behav. 93(4-5), 757-65, (2008)

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Role of CCK1 and Y2 receptors in activation of hindbrain neurons induced by intragastric administration of bitter taste receptor ligands Hao S. , et al. Am. J. Physiol. Regul. Integr. Comp. Physiol. 294, R33-38, (2008)

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Nasal solitary chemoreceptor cell responses to bitter and trigeminal stimulants in vitro. Gulbransen BD, Clapp TR, Finger TE, et al. J. Neurophysiol. 99(6), 2929-37, (2008)

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Constitutively active mutant gives novel insights into the mechanism of bitter taste receptor activation. Pydi SP, Bhullar RP, and Chelikani P J. Neurochem. 122(3), 537-44, (2012)

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Central Fos expression and conditioned flavor avoidance in rats following intragastric administration of bitter taste receptor ligands. Hao S, Dulake M, Espero E, et al. Am. J. Physiol. Regul. Integr. Comp. Physiol. 296(3), R528-36, (2009)

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The sugar meal of the African malaria mosquito Anopheles gambiae and how deterrent compounds interfere with it: a behavioural and neurophysiological study. Kessler S, Vlimant M, and Guerin PM J. Exp. Biol. 216(Pt 7), 1292-306, (2013)

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Riboflavin-binding protein is a novel bitter inhibitor. Maehashi K, Matano M, Nonaka M, et al. Chem. Senses 33(1), 57-63, (2008)

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Residual chemosensory capabilities in double P2X2/P2X3 purinergic receptor null mice: intraoral or postingestive detection? Hallock RM, Tatangelo M, Barrows J, et al. Chem. Senses 34(9), 799-808, (2009)

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Future bronchodilator therapy: a bitter pill to swallow? Clifford RL and Knox AJ Am. J. Physiol. Lung Cell. Mol. Physiol. 303(11), L953-5, (2012)

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Signalling mechanisms in mouse bitter responsive taste cells. Narukawa M, Minamisawa E, and Hayashi Y Neuroreport 20(10), 936-40, (2009)

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Adverse reactions associated with respirator fit testing of healthcare workers in British Columbia, Canada: a review of compensation claim cases. Youakim S Arch. Environ. Occup. Health 62(4), 197-200, (2007)

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Ongoing ingestive behavior is rapidly suppressed by a preabsorptive, intestinal "bitter taste" cue. Schier LA, Davidson TL, and Powley TL Am. J. Physiol. Regul. Integr. Comp. Physiol. 301(5), R1557-68, (2011)

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The impact of bittering agents on suicidal ingestions of antifreeze. White NC, Litovitz T, White MK, et al. Clin. Toxicol. (Phila.) 46(6), 507-14, (2008)

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Gustatory responsiveness to six bitter tastants in three species of nonhuman primates. Laska M, Rivas Bautista RM, and Hernandez Salazar LT J. Chem. Ecol. 35(5), 560-71, (2009)

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Final report of the safety assessment of Alcohol Denat., including SD Alcohol 3-A, SD Alcohol 30, SD Alcohol 39, SD Alcohol 39-B, SD Alcohol 39-C, SD Alcohol 40, SD Alcohol 40-B, and SD Alcohol 40-C, and the denaturants, Quassin, Brucine Sulfate/Brucine, and Denatonium Benzoate. Int. J. Toxicol. 27 Suppl 1, 1-43, (2008)

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Merck 14,2891

FT-NMR 1 (2), 1367:C / RegBook 1 (2), 1999:K / Structure Index 1, 319:C:8

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