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MedKoo Cat#: 531014 | Name: Denatonium benzoate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Denatonium, also known as Bitrex, is a bitterant (or bitter agonist). Denatonium activates bitter taste receptors on many cell types and plays important roles in chemical release, ciliary beating and smooth muscle relaxation through intracellular Ca(2+)-dependent pathways. Denatonium significantly effects cellular morphology, decreases cell proliferation and reduces the number of cells in S phase in a dose-dependent manner. Denatonium causes large amplitude swelling of mitochondria, which was confirmed by the loss of mitochondrial membrane potential, the down-regulation of Bcl-2 protein and the subsequent enhancement of the mitochondrial release of cytochrome c and Smac/DIABLO after denatonium treatment.

Chemical Structure

Denatonium benzoate
Denatonium benzoate
CAS#3734-33-6 (benzoate)

Theoretical Analysis

MedKoo Cat#: 531014

Name: Denatonium benzoate

CAS#: 3734-33-6 (benzoate)

Chemical Formula: C28H34N2O3

Exact Mass: 325.2274

Molecular Weight: 446.59

Elemental Analysis: C, 75.31; H, 7.67; N, 6.27; O, 10.75

Price and Availability

Size Price Availability Quantity
5g USD 250.00 2 Weeks
10g USD 350.00 2 Weeks
25g USD 650.00 2 Weeks
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Related CAS #
47324-98-1 (cation) 1674-99-3 (chloride) 3734-33-6 (benzoate)
Synonym
Denatonium benzoate; Bitrex, Aversion; THS 839; THS839; THS-839; Win 16568; Win16568; Win-16568; NSC 157658; NSC-157658; NSC157658
IUPAC/Chemical Name
N-benzyl-2-((2,6-dimethylphenyl)amino)-N,N-diethyl-2-oxoethan-1-aminium benzoate
InChi Key
VWTINHYPRWEBQY-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
O=C(NC1=C(C)C=CC=C1C)C[N+](CC)(CC2=CC=CC=C2)CC.O=C([O-])C3=CC=CC=C3
Appearance
White to off-white crystalline powder.
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 446.59 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Wen X, Zhou J, Zhang D, Li J, Wang Q, Feng N, Zhu H, Song Y, Li H, Bai C. Denatonium inhibits growth and induces apoptosis of airway epithelial cells through mitochondrial signaling pathways. Respir Res. 2015 Feb 5;16:13. doi: 10.1186/s12931-015-0183-9. PubMed PMID: 25652218; PubMed Central PMCID: PMC4326484. 2: Crosson GS, Sandmann E. Kinetic Study of Denatonium Sorption to Smectite Clay Minerals. Environ Eng Sci. 2013 Jun;30(6):311-316. PubMed PMID: 23781128; PubMed Central PMCID: PMC3680979. 3: Kwiatkowski A, Czerwicka M, Smulko J, Stepnowski P. Detection of denatonium benzoate (bitrex) remnants in noncommercial alcoholic beverages by Raman spectroscopy. J Forensic Sci. 2014 Sep;59(5):1358-63. doi: 10.1111/1556-4029.12461. Epub 2014 Mar 25. PubMed PMID: 24661259. 4: Firouzi MS, Firouzi M, Nabian MH, Zanjani LO, Zadegan SA, Kamrani RS, Rahimi-Movaghar V. The effects of picric acid (2,4,6-trinitrophenol) and a bite-deterrent chemical (denatonium benzoate) on autotomy in rats after peripheral nerve lesion. Lab Anim (NY). 2015 Apr;44(4):141-5. doi: 10.1038/laban.711. PubMed PMID: 25793680. 5: Bąchor R, Kluczyk A, Stefanowicz P, Szewczuk Z. Facile synthesis of deuterium-labeled denatonium cation and its application in the quantitative analysis of Bitrex by liquid chromatography-mass spectrometry. Anal Bioanal Chem. 2015 Aug;407(21):6557-61. doi: 10.1007/s00216-015-8815-y. Epub 2015 Jun 16. PubMed PMID: 26077748; PubMed Central PMCID: PMC4516867. 6: Pulkkinen V, Manson ML, Säfholm J, Adner M, Dahlén SE. The bitter taste receptor (TAS2R) agonists denatonium and chloroquine display distinct patterns of relaxation of the guinea pig trachea. Am J Physiol Lung Cell Mol Physiol. 2012 Dec 1;303(11):L956-66. doi: 10.1152/ajplung.00205.2012. Epub 2012 Sep 7. PubMed PMID: 22962016. 7: Kim KS, Egan JM, Jang HJ. Denatonium induces secretion of glucagon-like peptide-1 through activation of bitter taste receptor pathways. Diabetologia. 2014 Oct;57(10):2117-25. doi: 10.1007/s00125-014-3326-5. Epub 2014 Jul 13. Erratum in: Diabetologia. 2014 Nov;57(11):2428. PubMed PMID: 25016595; PubMed Central PMCID: PMC5160131. 8: Jung HY, Kim W, Yoo DY, Nam SM, Kim JW, Choi JH, Yoon YS, Kim HY, Hwang IK. Intragastric gavage with denatonium benzoate acutely induces neuronal activation in the solitary tract nucleus via the vagal afferent pathway. J Vet Sci. 2014 Dec;15(4):459-64. Epub 2014 Jun 20. PubMed PMID: 24962407; PubMed Central PMCID: PMC4269587. 9: Sakai H, Sato K, Kai Y, Chiba Y, Narita M. Denatonium and 6-n-Propyl-2-thiouracil, Agonists of Bitter Taste Receptor, Inhibit Contraction of Various Types of Smooth Muscles in the Rat and Mouse. Biol Pharm Bull. 2016;39(1):33-41. doi: 10.1248/bpb.b15-00426. Epub 2015 Nov 14. PubMed PMID: 26567724. 10: Rogachevskaja OA, Churbanov GD, Bystrova MF, Romanov RA, Kolesnikov SS. Stimulation of the extracellular Ca²⁺-sensing receptor by denatonium. Biochem Biophys Res Commun. 2011 Dec 16;416(3-4):433-6. doi: 10.1016/j.bbrc.2011.11.095. Epub 2011 Nov 28. PubMed PMID: 22142848. 11: Sakai H, Sato K, Kai Y, Chiba Y, Narita M. Denatonium and 6-n-Propyl-2-thiouracil, Agonists of Bitter Taste Receptor, Inhibit Contraction of Various Types of Smooth Muscles in the Rat and Mouse. Biol Pharm Bull. 2016;39(1):33-41. PubMed PMID: 27110632. 12: Berning CK, Griffith JF, Wild JE. Research on the effectiveness of denatonium benzoate as a deterrent to liquid detergent ingestion by children. Fundam Appl Toxicol. 1982 Jan-Feb;2(1):44-8. PubMed PMID: 7185601. 13: Klein-Schwartz W. Denatonium benzoate: review of efficacy and safety. Vet Hum Toxicol. 1991 Dec;33(6):545-7. Review. PubMed PMID: 1808826. 14: Hansen SR, Janssen C, Beasley VR. Denatonium benzoate as a deterrent to ingestion of toxic substances: toxicity and efficacy. Vet Hum Toxicol. 1993 Jun;35(3):234-6. Review. PubMed PMID: 8351798. 15: Sawano S, Seto E, Mori T, Hayashi Y. G-protein-dependent and -independent pathways in denatonium signal transduction. Biosci Biotechnol Biochem. 2005 Sep;69(9):1643-51. PubMed PMID: 16195580. 16: Ogura T, Mackay-Sim A, Kinnamon SC. Bitter taste transduction of denatonium in the mudpuppy Necturus maculosus. J Neurosci. 1997 May 15;17(10):3580-7. PubMed PMID: 9133381. 17: Straub SG, Mulvaney-Musa J, Yajima H, Weiland GA, Sharp GW. Stimulation of insulin secretion by denatonium, one of the most bitter-tasting substances known. Diabetes. 2003 Feb;52(2):356-64. PubMed PMID: 12540608. 18: Carey RM, Workman AD, Hatten KM, Siebert AP, Brooks SG, Chen B, Adappa ND, Palmer JN, Kennedy DW, Lee RJ, Cohen NA. Denatonium-induced sinonasal bacterial killing may play a role in chronic rhinosinusitis outcomes. Int Forum Allergy Rhinol. 2017 May 23. doi: 10.1002/alr.21949. [Epub ahead of print] PubMed PMID: 28544530. 19: Glendinning JI, Yiin YM, Ackroff K, Sclafani A. Intragastric infusion of denatonium conditions flavor aversions and delays gastric emptying in rodents. Physiol Behav. 2008 Mar 18;93(4-5):757-65. doi: 10.1016/j.physbeh.2007.11.029. Epub 2007 Nov 28. PubMed PMID: 18174110; PubMed Central PMCID: PMC2396241. 20: Ogura T, Margolskee RF, Kinnamon SC. Taste receptor cell responses to the bitter stimulus denatonium involve Ca2+ influx via store-operated channels. J Neurophysiol. 2002 Jun;87(6):3152-5. PubMed PMID: 12037215.

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