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D5765

Sigma-Aldrich

Denatonium benzoate

≥98%

Synonym(s):

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

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About This Item

Linear Formula:
C21H29N2O · C7H5O2
CAS Number:
3734-33-6
Molecular Weight:
446.58
Beilstein/REAXYS Number:
8179408
EC Number:
223-095-2
MDL number:
MFCD00031578
UNSPSC Code:
12352100
PubChem Substance ID:
57654112
NACRES:
NA.22

Quality Level

100

assay

≥98%

form

powder

mp

164-168 °C (lit.)

SMILES string

[O-]C(=O)c1ccccc1.CC[N+](CC)(CC(=O)Nc2c(C)cccc2C)Cc3ccccc3

InChI

1S/C21H28N2O.C7H6O2/c1-5-23(6-2,15-19-13-8-7-9-14-19)16-20(24)22-21-17(3)11-10-12-18(21)4;8-7(9)6-4-2-1-3-5-6/h7-14H,5-6,15-16H2,1-4H3;1-5H,(H,8,9)

InChI key

VWTINHYPRWEBQY-UHFFFAOYSA-N

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General description

Denatonium benzoate (DB) is an ionized compound made up of a negatively charged benzoic acid and quaternary ammonium cation (denatonium). It is used as an alcohol denaturant and flavor in pharmaceuticals. Additionally, used in products like soap, animal repellents, antifreeze.

Application

Denatonium benzoate is used:

  • To prepare anti-gnawing bio-polymer composites using zinc stearate (ZnSt) and capsicum oleoresin (CO) impregnated in silica (SiCO) and polybutylene succinate(PBS).

pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 2

flash_point_f

212.0 °F - closed cup

flash_point_c

100 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP6065
MKCN4024
MKCM4855
MKCL4602
MKCH5854

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W Klein-Schwartz
Veterinary and human toxicology, 33(6), 545-547 (1991-12-01)
The efficacy and toxicity studies on denatonium benzoate are limited and may be subject to varying interpretations when viewed in the context of a potential poisoning situation. Efficacy studies to date in children have shown that in a controlled environment
Anne Brockhoff et al.
Journal of agricultural and food chemistry, 55(15), 6236-6243 (2007-06-28)
Sesquiterpene lactones are a major class of natural bitter compounds occurring in vegetables and culinary herbs as well as in aromatic and medicinal plants, where they often represent the main gustatory and pharmacologically active component. Investigations on sesquiterpene lactones have
John Skelhorn et al.
Current biology : CB, 17(17), 1479-1483 (2007-08-25)
Toxic prey advertise their unprofitability to predators via conspicuous aposematic coloration [1]. It is widely accepted that avoidance learning by naive predators is fundamental in generating selection for aposematism [2, 3] and mimicry [4, 5] (where species share the same
S R Hansen et al.
Veterinary and human toxicology, 35(3), 234-236 (1993-06-01)
When ingested at 10 ppm by human beings, denatonium benzoate has an extremely bitter, unpleasant taste. The addition of denatonium benzoate to liquid dish detergents and orange juice reduces the amount ingested by children. The toxicity of denatonium benzoate is
Sami Damak et al.
Chemical senses, 31(3), 253-264 (2006-01-27)
Trpm5 is a calcium-activated cation channel expressed selectively in taste receptor cells. A previous study reported that mice with an internal deletion of Trpm5, lacking exons 15-19 encoding transmembrane segments 1-5, showed no taste-mediated responses to bitter, sweet, and umami
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