denatonium benzoate
benzyldiethyl[(2,6-xylylcarbamoyl)methyl]ammonium benzoate
 
Notes:
very bitter compound; induces uriticaria & asthma.
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benzyl-[2-(2,6-dimethylanilino)-2-oxoethyl]-diethylazanium benzoate (Click)
CAS Number: 3734-33-6Picture of molecule
ECHA EINECS - REACH Pre-Reg: 223-095-2
FDA UNII: M5BA6GAF1O
Beilstein Number: 8179408
MDL: MFCD00031578
Molecular Weight: 446.59058000
Formula: C28 H34 N2 O3
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: certain adjuvants and production aids
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Appearance: white crystalline powder (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 168.00 °C. @ 760.00 mm Hg
Flash Point: > 200.00 °F. TCC ( > 93.33 °C. )
logP (o/w): 0.085 (est)
Soluble in:
 water, 428.9 mg/L @ 25 °C (est)
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Organoleptic Properties:
Odor Strength: low ,
recommend smelling in a 0.01 % solution or less
Odor Description:
at 100.00 %. 
bland
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: denaturants
masking agents
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Suppliers:
Santa Cruz Biotechnology
For experimental / research use only.
Denatonium Benzoate ≥99%
Sigma-Aldrich: Aldrich
For experimental / research use only.
Denatonium Benzoate ≥98%
Silver Fern Chemical
Denatonium Benzoate
Odor: characteristic
Use: Denatonium benzoate is used in the food and beverage industry as well as a solvent in many household and personal care products.
Universal Preserv-A-Chem Inc.
DENATONIUM BENZOATE GRAN NF
Universal Preserv-A-Chem Inc.
DENATONIUM BENZOATE
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Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 22 - Harmful if swallowed.
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 20/21 - When using do not eat, drink or smoke.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 37/39 - Wear suitable gloves and eye/face protection.
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50  584 mg/kg
BEHAVIORAL: TREMOR BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA
National Technical Information Service. Vol. PB81-139339

oral-rabbit LD50  508 mg/kg
BEHAVIORAL: TREMOR BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA
National Technical Information Service. Vol. PB81-139339

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: certain adjuvants and production aids
 
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Safety References:
European Food Safety Authority (EFSA) reference(s):
Conclusion on the peer review of the pesticide risk assessment of the active substance denatonium benzoate (approved as denathonium benzoate)
View page or View pdf
EPI System: View
ClinicalTrials.gov: search
Daily Med: search
Cancer Citations: Search
Toxicology Citations: Search
NLM Developmental and Reproductive Toxicity: Search
EPA Substance Registry Services (TSCA): 3734-33-6
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 19518
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 2
 benzyl-[2-(2,6-dimethylanilino)-2-oxoethyl]-diethylazanium benzoate
Chemidplus: 0003734336
RTECS: BO6650000 for cas# 3734-33-6
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References:
 benzyl-[2-(2,6-dimethylanilino)-2-oxoethyl]-diethylazanium benzoate
NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 3734-33-6
Pubchem (cid): 19518
Pubchem (sid): 134985655
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
HMDB (The Human Metabolome Database): Search
Export Tariff Code: 2924.29.4400
Household Products: Search
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
 denaturants 
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Occurrence (nature, food, other): note
 not found in nature
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Synonyms:
 ammonium, benzyldiethyl((2,6-xylylcarbamoyl)methyl)-, benzoate
 benzenemethanaminium, N-(2-((2,6-dimethylphenyl)amino)-2-oxoethyl)-N,N-diethyl-, benzoate
 benzenemethanaminium, N-[2-[(2,6-dimethylphenyl)amino]-2-oxoethyl]-N,N-diethyl-, benzoate
 benzenemethanaminium, N-[2-[(2,6-dimethylphenyl)amino]-2-oxoethyl]-N,N-diethyl-, benzoate (1:1)
 benzyl diethyl (2,6-xylyl carbamoyl methyl) ammonium benzoate
 benzyl-[(2,6-dimethylphenylcarbamoyl)methyl]diethylammonium benzoate
 benzyl-[2-(2,6-dimethylanilino)-2-oxoethyl]-diethylazanium benzoate
N-benzyl-2-[(2,6-dimethylphenyl)amino]-N,N-diethyl-2-oxoethanaminium benzoate
 benzyldiethyl((2,6-xylylcarbamoyl)methyl)ammonium benzoate
 benzyldiethyl(2,6-xylyl- carbamoyl- methyl)- ammonium benzoate
 benzyldiethyl[(2,6-xylylcarbamoyl)methyl]ammonium benzoate
 bitrex
 denatoniumbenzoate
N,N-diethyl-N-[(2,6-dimethylphenyl- carbamoyl)- methyl]- benzyl- ammonium benzoate
N-(2-((2,6-dimethyl phenyl)amino)-2-oxoethyl)-N,N-diethyl benzene methanaminium benzoate
N-(2-((2,6-dimethylphenyl)amino)-2-oxoethyl)-N,N-diethylbenzeneme- thanaminium benzoate
((2,6-xylylcarbamoyl)methyl)diethyl benzyl ammonium benzoate
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Articles:
PubMed: Age-related differences in bitter taste and efficacy of bitter blockers.
PubMed: Denatonium induces secretion of glucagon-like peptide-1 through activation of bitter taste receptor pathways.
PubMed: Intragastric gavage of denatonium benzoate acutely induces the neuronal activation in the nucleus of solitary tract via the vagal afferent pathway.
PubMed: Effect of five taste ligands on the release of CCK from an enteroendocrine cell line, STC-1.
PubMed: 6-methoxyflavanones as bitter taste receptor blockers for hTAS2R39.
PubMed: Detection of Denatonium Benzoate (Bitrex) Remnants in Noncommercial Alcoholic Beverages by Raman Spectroscopy.
PubMed: Bitter and sweet taste receptors regulate human upper respiratory innate immunity.
PubMed: A Comparative Evaluation of Condylar Guidance Value from Radiograph with Interocclusal Records made During Jaw Relation and Try-in: A Pilot Study.
PubMed: A novel human receptor involved in bitter tastant detection identified using Dictyostelium discoideum.
PubMed: Occupational hazards associated with endoscope high-level disinfection: case vignettes, review of literature and recommendations for mitigation.
PubMed: The human bitter taste receptor TAS2R10 is tailored to accommodate numerous diverse ligands.
PubMed: The sugar meal of the African malaria mosquito Anopheles gambiae and how deterrent compounds interfere with it: a behavioural and neurophysiological study.
PubMed: Future bronchodilator therapy: a bitter pill to swallow?
PubMed: The bitter taste receptor (TAS2R) agonists denatonium and chloroquine display distinct patterns of relaxation of the guinea pig trachea.
PubMed: Bitter taste stimuli induce differential neural codes in mouse brain.
PubMed: Constitutively active mutant gives novel insights into the mechanism of bitter taste receptor activation.
PubMed: Investigating the effect of emetic compounds on chemotaxis in Dictyostelium identifies a non-sentient model for bitter and hot tastant research.
PubMed: Ongoing ingestive behavior is rapidly suppressed by a preabsorptive, intestinal "bitter taste" cue.
PubMed: Functional bitter taste receptors are expressed in brain cells.
PubMed: Responses of single chorda tympani taste fibers of the calf (Bos taurus).
PubMed: Nasal chemosensory cells use bitter taste signaling to detect irritants and bacterial signals.
PubMed: Residual chemosensory capabilities in double P2X2/P2X3 purinergic receptor null mice: intraoral or postingestive detection?
PubMed: Signalling mechanisms in mouse bitter responsive taste cells.
PubMed: Gustatory responsiveness to six bitter tastants in three species of nonhuman primates.
PubMed: Gustation in fish: search for prototype of taste perception.
PubMed: Central Fos expression and conditioned flavor avoidance in rats following intragastric administration of bitter taste receptor ligands.
PubMed: UV-vis spectrophotometric method for the quantitation of all the components of Italian general denaturant and its application to check the conformity of alcohol samples.
PubMed: Construction of a taste-blind medaka fish and quantitative assay of its preference-aversion behavior.
PubMed: 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.
PubMed: The impact of bittering agents on suicidal ingestions of antifreeze.
PubMed: Adverse reactions associated with respirator fit testing of healthcare workers in British Columbia, Canada: a review of compensation claim cases.
PubMed: Nasal solitary chemoreceptor cell responses to bitter and trigeminal stimulants in vitro.
PubMed: Responses of the ciliates tetrahymena and paramecium to vertebrate odorants and tastants.
PubMed: A non-invasive method for ending thumb- and fingersucking habits.
PubMed: Intragastric infusion of denatonium conditions flavor aversions and delays gastric emptying in rodents.
PubMed: The taste transduction channel TRPM5 is a locus for bitter-sweet taste interactions.
PubMed: Role of CCK1 and Y2 receptors in activation of hindbrain neurons induced by intragastric administration of bitter taste receptor ligands.
PubMed: Riboflavin-binding protein is a novel bitter inhibitor.
PubMed: Predators' toxin burdens influence their strategic decisions to eat toxic prey.
PubMed: Broad tuning of the human bitter taste receptor hTAS2R46 to various sesquiterpene lactones, clerodane and labdane diterpenoids, strychnine, and denatonium.
PubMed: Characterization of ligands for fish taste receptors.
PubMed: Simulated workplace protection factors for half-facepiece respiratory protective devices.
PubMed: Single neurons in the nucleus of the solitary tract respond selectively to bitter taste stimuli.
PubMed: Comparison of performance of three different types of respiratory protection devices.
PubMed: Bitter stimuli induce Ca2+ signaling and CCK release in enteroendocrine STC-1 cells: role of L-type voltage-sensitive Ca2+ channels.
PubMed: Errors associated with three methods of assessing respirator fit.
PubMed: Trpm5 null mice respond to bitter, sweet, and umami compounds.
PubMed: Differential covariation in taste responsiveness to bitter stimuli in rats.
PubMed: Chemotaxis of the nematode Caenorhabditis elegans toward cycloheximide and quinine hydrochloride.
PubMed: Acute ethanol intoxication after consumption of hairspray.
PubMed: G-protein-dependent and -independent pathways in denatonium signal transduction.
PubMed: PLCbeta2-independent behavioral avoidance of prototypical bitter-tasting ligands.
PubMed: Bitterness suppression with zinc sulfate and na-cyclamate: a model of combined peripheral and central neural approaches to flavor modification.
PubMed: Neural representation of bitter taste in the nucleus of the solitary tract.
PubMed: Inbred mouse strains C57BL/6J and DBA/2J vary in sensitivity to a subset of bitter stimuli.
PubMed: Haplotypes at the Tas2r locus on distal chromosome 6 vary with quinine taste sensitivity in inbred mice.
PubMed: Genomic organization, expression, and function of bitter taste receptors (T2R) in mouse and rat.
PubMed: Characterization of bitter taste responses of intestinal STC-1 cells.
PubMed: Umami taste responses are mediated by alpha-transducin and alpha-gustducin.
PubMed: Identification of ligands for two human bitter T2R receptors.
PubMed: Diverse bitter stimuli elicit highly similar patterns of Fos-like immunoreactivity in the nucleus of the solitary tract.
PubMed: Fitting characteristics of eighteen N95 filtering-facepiece respirators.
PubMed: Was it necessary to add Bitrex (denatonium benzoate) to automotive products?
PubMed: Saccharin stimulates the "deterrent" cell in the blowfly: behavioral and electrophysiological evidence.
PubMed: The distinctiveness of ionic and nonionic bitter stimuli.
PubMed: Role of the G-protein subunit alpha-gustducin in taste cell responses to bitter stimuli.
PubMed: A psychophysical investigation of binary bitter-compound interactions.
PubMed: Comparison of the responses of the chorda tympani and glossopharyngeal nerves to taste stimuli in C57BL/6J mice.
PubMed: Partial rescue of taste responses of alpha-gustducin null mice by transgenic expression of alpha-transducin.
PubMed: Comparison of five methods for fit-testing N95 filtering-facepiece respirators.
PubMed: Rats fail to discriminate quinine from denatonium: implications for the neural coding of bitter-tasting compounds.
PubMed: Covariation in individuals' sensitivities to bitter compounds: evidence supporting multiple receptor/transduction mechanisms.
PubMed: Effect of compound sequence on bitterness enhancement.
PubMed: Bitter taste transduced by PLC-beta(2)-dependent rise in IP(3) and alpha-gustducin-dependent fall in cyclic nucleotides.
PubMed: Taste receptor cells that discriminate between bitter stimuli.
PubMed: Cellular responses of NG108-15 and SK-N-MC lines to sweet and bitter tastants as measured by extracellular acidification rates.
PubMed: Comparison of methyl anthranilate and denatonium benzoate as aversants for learning in chicks.
PubMed: Oregon's Toxic Household Products Law.
PubMed: G protein betagamma complexes in circumvallate taste cells involved in bitter transduction.
PubMed: Capability of respirator wearers to detect aerosolized qualitative fit test agents (sweetener and Bitrex) with known fixed leaks.
PubMed: T2Rs function as bitter taste receptors.
PubMed: Comparison of N95 disposable filtering facepiece fits using bitrex qualitative and TSI Portacount quantitative fit testing.
PubMed: Blocking taste receptor activation of gustducin inhibits gustatory responses to bitter compounds.
PubMed: Transduction for sweet taste of saccharin may involve both inositol 1,4,5-trisphosphate and cAMP pathways in the fungiform taste buds in C57BL mice.
PubMed: Patch clamp recording of the responses to three bitter stimuli in mouse taste cells.
PubMed: Training and characterization of a quinine taste discrimination in rhesus monkeys.
PubMed: Identification of a phospholipase C beta subtype in rat taste cells.
PubMed: Flavor avoidance learning and its implications in reducing strychnine baiting hazards to nontarget animals.
PubMed: Physico-chemical characterization of human von Ebner gland protein expressed in Escherichia coli: implications for its physiological role.
PubMed: Increase in inositol 1,4,5-triphosphate levels of the fungiform papilla in response to saccharin and bitter substances in mice.
PubMed: Responses of cultured rat trigeminal ganglion neurons to bitter tastants.
PubMed: Analysis of denatonium benzoate in Oregon consumer products by HPLC.
PubMed: Quinine suppression of single facial taste fiber responses in the channel catfish.
PubMed: Response of domestic chicks to methyl anthranilate odour
PubMed: Bitter taste transduction of denatonium in the mudpuppy Necturus maculosus.
PubMed: Neural responses to bitter compounds in rats.
PubMed: Response of pigs to bitter-tasting compounds.
PubMed: Primate sense of taste: behavioral and single chorda tympani and glossopharyngeal nerve fiber recordings in the rhesus monkey, Macaca mulatta.
PubMed: Transduction of bitter and sweet taste by gustducin.
PubMed: Rapid kinetics of second messenger production in bitter taste.
PubMed: Development of a new qualitative test for fit testing respirators.
PubMed: An evaluation of repellents to suppress browsing by possums.
PubMed: Bittering agents: their potential application in reducing ingestions of engine coolants and windshield wash.
PubMed: Coupling of bitter receptor to phosphodiesterase through transducin in taste receptor cells.
PubMed: Bitter taste in single chorda tympani taste fibers from chimpanzee.
PubMed: Denatonium bitter tasting among transgenic mice expressing rat von Ebner's gland protein.
PubMed: Generation of inositol phosphates in bitter taste transduction.
PubMed: Genetics of bitter perception in mice.
PubMed: Taste perception of bitter compounds in young and elderly persons: relation to lipophilicity of bitter compounds.
PubMed: Response latency of gerbils and hamsters to nuts flavoured with bitter-tasting substances.
PubMed: Tolerance of bitter compounds by an herbivore,Cavia porcellus.
PubMed: The role of aversive bittering agents in the prevention of pediatric poisonings.
PubMed: The effect of sweeteners on bitter taste in young and elderly subjects.
PubMed: Denatonium benzoate as a deterrent to ingestion of toxic substances: toxicity and efficacy.
PubMed: Relationships between ingestion and gustatory perception of caffeine.
PubMed: Denatonium benzoate: review of efficacy and safety.
PubMed: Plastic membrane ion-selective electrode for the determination of denatonium benzoate (Bitrex).
PubMed: Taste reactivity in the hamster.
PubMed: Bittering agents in the prevention of accidental poisoning: children's reactions to denatonium benzoate (Bitrex).
PubMed: A simple method for reducing autotomy in rats after peripheral nerve lesions.
PubMed: A method for isolating and patch-clamping single mammalian taste receptor cells.
PubMed: Drinking drivers in Sweden who consume denatured alcohol preparations: an analytical-toxicological study.
PubMed: The problems of taste in placebo matching: an evaluation of zinc gluconate for the common cold.
PubMed: Research on the effectiveness of denatonium benzoate as a deterrent to liquid detergent ingestion by children.
PubMed: Contact urticaria and asthma from denatonium benzoate (Bitrex).
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