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![4-(Acetoxymethyl)nitrosamino]-1-(3-pyridyl)-1-butanone (CAS 127686-49-1) - chemical structure image](https://media.scbt.com/product/4-acetoxymethyl-nitrosamino-1-3-pyridyl-1-butanone-127686-49-1-structure_08_74_t_87436.jpg "Molecular structure of 4-(Acetoxymethyl)nitrosamino]-1-(3-pyridyl)-1-butanone, CAS Number: 127686-49-1")
Molecular structure of 4-(Acetoxymethyl)nitrosamino]-1-(3-pyridyl)-1-butanone, CAS Number: 127686-49-1
4-(Acetoxymethyl)nitrosamino]-1-(3-pyridyl)-1-butanone (CAS 127686-49-1)
Alternate Names:
Acetoxymethyl-NNK
Application:
4-(Acetoxymethyl)nitrosamino]-1-(3-pyridyl)-1-butanone is a NKK precursor
CAS Number:
127686-49-1
Molecular Weight:
265.27
Molecular Formula:
C12H15N3O4
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
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
4-(Acetoxymethylnitrosamino)-1-(3-pyridyl)-1-butanone is a carcinogen and tobacco-specific nitrosamine 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) precursor. It is used to investigate the impact of nitric oxide (NO) on biological systems by enhancing cellular NO levels, which can result in various physiological effects. These effects encompass increased cell proliferation, angiogenesis, and apoptosis. Moreover, 4-(Acetoxymethylnitrosamino)-1-(3-pyridyl)-1-butanone is believed to hinder the release of inflammatory mediators, including cytokines and chemokines.
4-(Acetoxymethyl)nitrosamino]-1-(3-pyridyl)-1-butanone (CAS 127686-49-1) References
- Characterization and mapping of DNA damage induced by reactive metabolites of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) at nucleotide resolution in human genomic DNA. | Cloutier, JF., et al. 2001. J Mol Biol. 313: 539-57. PMID: 11676538
- Cytokine production by alveolar macrophages is down regulated by the alpha-methylhydroxylation pathway of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK). | Proulx, LI., et al. 2004. Carcinogenesis. 25: 997-1003. PMID: 14764458
- 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone, a component of tobacco smoke, modulates mediator release from human bronchial and alveolar epithelial cells. | Proulx, LI., et al. 2005. Clin Exp Immunol. 140: 46-53. PMID: 15762874
- Sensitivity to NNKOAc is associated with renal cancer risk. | Clague, J., et al. 2009. Carcinogenesis. 30: 706-10. PMID: 19237609
- Solvolysis of model compounds for alpha-hydroxylation of N'-nitrosonornicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone: evidence for a cyclic oxonium ion intermediate in the alkylation of nucleophiles. | Spratt, TE., et al. 1990. Chem Res Toxicol. 3: 350-6. PMID: 2133084
- Formation and repair of pyridyloxobutyl DNA adducts and their relationship to tumor yield in A/J mice. | Urban, AM., et al. 2012. Chem Res Toxicol. 25: 2167-78. PMID: 22928598
- Anthocyanin-rich haskap (Lonicera caerulea L.) berry extracts reduce nitrosamine-induced DNA damage in human normal lung epithelial cells in vitro. | Amararathna, M., et al. 2020. Food Chem Toxicol. 141: 111404. PMID: 32413456
- Vitamin-Containing Antioxidant Formulation Reduces Carcinogen-Induced DNA Damage through ATR/Chk1 Signaling in Bronchial Epithelial Cells In Vitro. | Merlin, JPJ., et al. 2021. Biomedicines. 9: PMID: 34829893
- A Dietary Antioxidant Formulation Ameliorates DNA Damage Caused by γ-Irradiation in Normal Human Bronchial Epithelial Cells In Vitro. | Merlin, JPJ., et al. 2022. Antioxidants (Basel). 11: PMID: 35883898
- Genistein and Procyanidin B2 Reduce Carcinogen-Induced Reactive Oxygen Species and DNA Damage through the Activation of Nrf2/ARE Cell Signaling in Bronchial Epithelial Cells In Vitro. | Suraweera, TL., et al. 2023. Int J Mol Sci. 24: PMID: 36835090
- Pyridyloxobutylation of guanine residues by 4-[(acetoxymethyl)nitrosamino]-1-(3-pyridyl)-1-butanone generates substrates of O6-alkylguanine-DNA alkyltransferase. | Liu, XK., et al. 1996. Chem Res Toxicol. 9: 949-53. PMID: 8870981
- Elevated 8-hydroxy-2'-deoxyguanosine levels in lung DNA of A/J mice and F344 rats treated with 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and inhibition by dietary 1,4-phenylenebis(methylene)selenocyanate. | Rosa, JG., et al. 1998. Carcinogenesis. 19: 1783-8. PMID: 9806159
- P1.01-015 Polyphenols-Rich Fruit Extracts Prevent Tobacco Specific Nitrosamine-Induced DNA Damage in Lung Epithelial Cells Topic: Protective Factors, Risk Reduction, Smoking Cessation | Amararathna, D. I. M., Hoskin, D. W., Johnston, M., & Rupasinghe, H. P. V. 2017. Journal of Thoracic Oncology. 12(1): S456-S457.
Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
4-(Acetoxymethyl)nitrosamino]-1-(3-pyridyl)-1-butanone, 10 mg | sc-206764 | 10 mg | $323.00 |