Molecular structure of Denatonium benzoate, CAS Number: 3734-33-6
Denatonium benzoate (CAS 3734-33-6)
Alternate Names:
N,N-Diethyl-N-[(2,6-dimethylphenylcarbamoyl)methyl]benzylammonium benzoate; Benzyldiethyl(2,6-xylylcarbamoylmethyl)ammonium benzoate; THS 839
CAS Number:
3734-33-6
Purity:
≥99%
Molecular Weight:
446.58
Molecular Formula:
C21H29N2O•C7H5O2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
Denatonium benzoate, classified as a bittering agent, serves as an analytical reference standard with unique properties. It activates bitter taste receptors in various cell types, impacting chemical release, ciliary beating, and smooth muscle relaxation through intracellular Ca(2+)-dependent pathways. Additionally, Denatonium benzoate has shown significant effects on cellular morphology, reducing cell proliferation and the number of cells in the S phase in a dose-dependent manner. Notably, it induces considerable swelling of mitochondria, leading to the loss of mitochondrial membrane potential and the down-regulation of Bcl-2 protein. Consequently, Denatonium benzoate enhances the release of cytochrome c and Smac/DIABLO from mitochondria following its treatment.
Denatonium benzoate (CAS 3734-33-6) References
- Comparison of methyl anthranilate and denatonium benzoate as aversants for learning in chicks. | Richard, S. and Davies, DC. 2000. Physiol Behav. 70: 521-5. PMID: 11111006
- Rats fail to discriminate quinine from denatonium: implications for the neural coding of bitter-tasting compounds. | Spector, AC. and Kopka, SL. 2002. J Neurosci. 22: 1937-41. PMID: 11880524
- Bitter taste stimuli induce differential neural codes in mouse brain. | Wilson, DM., et al. 2012. PLoS One. 7: e41597. PMID: 22844505
- 6-methoxyflavanones as bitter taste receptor blockers for hTAS2R39. | Roland, WS., et al. 2014. PLoS One. 9: e94451. PMID: 24722342
- Intragastric gavage with denatonium benzoate acutely induces neuronal activation in the solitary tract nucleus via the vagal afferent pathway. | Jung, HY., et al. 2014. J Vet Sci. 15: 459-64. PMID: 24962407
- The effects of picric acid (2,4,6-trinitrophenol) and a bite-deterrent chemical (denatonium benzoate) on autotomy in rats after peripheral nerve lesion. | Firouzi, MS., et al. 2015. Lab Anim (NY). 44: 141-5. PMID: 25793680
- Evaluation of the Bitterness-Masking Effect of Powdered Roasted Soybeans. | Makita, Y., et al. 2016. Foods. 5: PMID: 28231139
- Responsiveness Expressions of Bitter Taste Receptors Against Denatonium Benzoate and Genistein in the Heart, Spleen, Lung, Kidney, and Bursa Fabricius of Chinese Fast Yellow Chicken. | Hamdard, E., et al. 2019. Animals (Basel). 9: PMID: 31390726
- Denatonium Benzoate-Induces Oxidative Stress in the Heart and Kidney of Chinese Fast Yellow Chickens by Regulating Apoptosis, Autophagy, Antioxidative Activities and Bitter Taste Receptor Gene Expressions. | Hamdard, E., et al. 2019. Animals (Basel). 9: PMID: 31546822
- Denatonium as a Bitter Taste Receptor Agonist Modifies Transcriptomic Profile and Functions of Acute Myeloid Leukemia Cells. | Salvestrini, V., et al. 2020. Front Oncol. 10: 1225. PMID: 32793492
- Divergent bitter and sweet taste perception intensity in chronic rhinosinusitis patients. | Lin, C., et al. 2021. Int Forum Allergy Rhinol. 11: 857-865. PMID: 32846055
- Denatonium benzoate bitter taste perception in chronic rhinosinusitis subgroups. | Civantos, AM., et al. 2021. Int Forum Allergy Rhinol. 11: 967-975. PMID: 32885614
- Development and application of diffusive gradients in thin-films for in situ sampling of the bitterest chemical - denatonium benzoate in waters. | Liu, S., et al. 2021. J Hazard Mater. 418: 126393. PMID: 34329009
- Human intestinal bitter taste receptors regulate innate immune responses and metabolic regulators in obesity. | Liszt, KI., et al. 2022. J Clin Invest. 132: PMID: 34784295
- The effect of adulteration with a bitter tastant, denatonium benzoate, on the reinforcing value of sucrose. | Bradshaw, CM. 2022. Behav Processes. 203: 104771. PMID: 36330898
Inhibitor of:
KRTAP10-12, T1R3, T2R05, T2R06, T2R09, T2R13, T2R14, T2R23, T2R24, T2R26, T2R41, T2R42, T2R48, T2R9, TAS1R (taste receptor; GPCR), Trcg1, and V1RH1.Activator of:
Olfactorin, T2R04, T2R05, T2R06, T2R09, T2R1, T2R10, T2R13, T2R134, T2R14, T2R15, T2R16, T2R17, T2R18, T2R20, T2R21, T2R22, T2R23, T2R24, T2R3, T2R31, T2R37, T2R38, T2R39, T2R4, T2R41, T2R42, T2R43, T2R44, T2R45, T2R47, T2R48, T2R49, T2R50, T2R6, T2R60, T2R7, T2R8, T2R9, Tas2r102, Tas2r103, Tas2r114, Tas2r125, Tas2r140, Tas2r143, and Vmn1r124.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Denatonium benzoate, 1 g | sc-234525 | 1 g | $31.00 | |||
Denatonium benzoate, 5 g | sc-234525A | 5 g | $46.00 | |||
Denatonium benzoate, 25 g | sc-234525B | 25 g | $138.00 | |||
Denatonium benzoate, 100 g | sc-234525C | 100 g | $464.00 | |||
Denatonium benzoate, 250 g | sc-234525D | 250 g | $903.00 |