Ethoxyquin
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
| Common Name | Ethoxyquin(F05571) |
| 2D Structure | |
| Description | Ethoxyquin is an antioxidant used in animal feeds and for the preservation of colour in the production of chili powder, paprika and ground chilli. Ethoxyquin is formerly used as an agricultural pesticide/herbicide, now superseded. Also used as a post-harvest dip for apples and pears to prevent scald. |
| FRCD ID | F05571 |
| CAS Number | 91-53-2 |
| PubChem CID | 3293 |
| Formula | C14H19NO |
| IUPAC Name | 6-ethoxy-2,2,4-trimethyl-1H-quinoline |
| InChI Key | DECIPOUIJURFOJ-UHFFFAOYSA-N |
| InChI | InChI=1S/C14H19NO/c1-5-16-11-6-7-13-12(8-11)10(2)9-14(3,4)15-13/h6-9,15H,5H2,1-4H3 |
| Canonical SMILES | CCOC1=CC2=C(C=C1)NC(C=C2C)(C)C |
| Isomeric SMILES | CCOC1=CC2=C(C=C1)NC(C=C2C)(C)C |
| Synonyms |
6-Ethoxy-2,2,4-trimethyl-1,2-dihydroquinoline
ethoxyquin
91-53-2
Ethoxyquine
Santoquin
Santoquine
Niflex
Antioxidant EC
Santoflex A
Santoflex AW
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Quinolines and derivatives |
| Subclass | Quinolones and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Hydroquinolones |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Dihydroquinolone - Dihydroquinoline - Alkyl aryl ether - Secondary aliphatic/aromatic amine - Benzenoid - Azacycle - Secondary amine - Ether - Amine - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as hydroquinolones. These are compounds containing a hydrogenated quinoline bearing a ketone group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 217.312 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 2 |
| Complexity | 283 |
| Monoisotopic Mass | 217.147 |
| Exact Mass | 217.147 |
| XLogP | 3.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 16 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9467 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.6978 |
| P-glycoprotein Substrate | Substrate | 0.6954 |
| P-glycoprotein Inhibitor | Inhibitor | 0.8303 |
| Non-inhibitor | 0.8382 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7503 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6018 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8646 |
| CYP450 2D6 Substrate | Non-substrate | 0.6294 |
| CYP450 3A4 Substrate | Substrate | 0.6844 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9171 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.8948 |
| CYP450 2D6 Inhibitor | Inhibitor | 0.8933 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8994 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.7959 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.9738 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8945 |
| Non-inhibitor | 0.6263 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.9183 |
| Fish Toxicity | High FHMT | 0.7645 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9952 |
| Honey Bee Toxicity | High HBT | 0.7693 |
| Biodegradation | Not ready biodegradable | 0.9969 |
| Acute Oral Toxicity | III | 0.7811 |
| Carcinogenicity (Three-class) | Non-required | 0.6935 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.3166 | LogS |
| Caco-2 Permeability | 1.7812 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.4538 | LD50, mol/kg |
| Fish Toxicity | 0.1029 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.0745 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Comprehensive characterization of ethoxyquin transformation products in fish feedby traveling-wave ion mobility spectrometry coupled to quadrupole time-of-flight mass spectrometry. | Anal Chim Acta | 2017 May 1 | 28366214 |
| Land Spreading of Wastewaters from the Fruit-Packaging Industry and Potential Effects on Soil Microbes: Effects of the Antioxidant Ethoxyquin and Its Metabolites on Ammonia Oxidizers. | Appl Environ Microbiol | 2016 Jan 15 | 26590271 |
| Dissipation, metabolism and sorption of pesticides used in fruit-packagingplants: Towards an optimized depuration of their pesticide-contaminatedagro-industrial effluents. | Sci Total Environ | 2015 Oct 15 | 26042894 |
| Application of zirconium dioxide nanoparticle sorbent for the clean-up step inpost-harvest pesticide residue analysis. | Talanta | 2015 Nov 1 | 26452791 |
| Screening of pesticides and polycyclic aromatic hydrocarbons in feeds and fishtissues by gas chromatography coupled to high-resolution mass spectrometry using atmospheric pressure chemical ionization. | J Agric Food Chem | 2014 Mar 12 | 24559176 |
| Effect of dietary antioxidant and increasing corn oil inclusion on milk fat yieldand fatty acid composition in dairy cattle. | J Dairy Sci | 2014 Dec | 25306271 |
| Supplementing antioxidants to pigs fed diets high in oxidants: I. Effects ongrowth performance, liver function, and oxidative status. | J Anim Sci | 2014 Dec | 25367515 |
| Ensuring selectivity and sensitivity by timed- and ultra-selective reactionmonitoring during gas chromatography-tandem mass spectrometric determination ofpesticides. | J Chromatogr A | 2013 Nov 29 | 24161146 |
| β-Carotene assay revisited. application to characterize and quantify antioxidant and prooxidant activities in a microplate. | J Agric Food Chem | 2012 Sep 12 | 22849655 |
| Investigations on the metabolism and potentially adverse effects of ethoxyquindimer, a major metabolite of the synthetic antioxidant ethoxyquin in salmonmuscle. | J Food Prot | 2011 Sep | 21902931 |
| Determination of ethoxyquin by high-performance liquid chromatography withfluorescence detection and its application to the survey of residues in foodproducts of animal origin. | J AOAC Int | 2010 Jan-Feb | 20334189 |
| Profiling of compounds and degradation products from the postharvest treatment ofpears and apples by ultra-high pressure liquid chromatographyquadrupole-time-of-flight mass spectrometry. | Talanta | 2010 Apr 15 | 20188921 |
| Accumulation and depuration of the synthetic antioxidant ethoxyquin in the muscleof Atlantic salmon (Salmo salar L.). | Food Chem Toxicol | 2008 May | 18329775 |
| Evaluation of PCDD/Fs characterization in animal feed and feed additives. | Chemosphere | 2007 Sep | 17604812 |
| Assessment of the stability of pesticides during the cryogenic processing offruits and vegetables. | Food Addit Contam | 2007 Nov | 17852403 |
| Hepatic metabolism, phase I and II biotransformation enzymes in Atlantic salmon(Salmo Salar, L) during a 12 week feeding period with graded levels of thesynthetic antioxidant, ethoxyquin. | Food Chem Toxicol | 2007 May | 17150295 |
| Identification of unknown pesticides in fruits using ultra-performance liquidchromatography-quadrupole time-of-flight mass spectrometry. Imazalil as a casestudy of quantification. | J Chromatogr A | 2007 Dec 28 | 18021786 |
| Differences in ethoxyquin nephrotoxicity between male and female F344 rats. | Food Chem Toxicol | 2003 Feb | 12480297 |
| Induction of chromosome aberrations in cultured human lymphocytes treated withethoxyquin. | Mutat Res | 2003 Dec 9 | 14644360 |
| Carbohydrate fermentation and nitrogen metabolism of a finishing beef diet byruminal microbes in continuous cultures as affected by ethoxyquin and(or)supplementation of monensin and tylosin. | J Anim Sci | 2002 Apr | 12002320 |
Targets
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
- Gene Name:
- CYP2D6
- Uniprot ID:
- P10635
- Molecular Weight:
- 55768.94 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
- Gene Name:
- NR1I2
- Uniprot ID:
- O75469
- Molecular Weight:
- 49761.245 Da
References
- Kojima H, Sata F, Takeuchi S, Sueyoshi T, Nagai T: Comparative study of human and mouse pregnane X receptor agonistic activity in 200 pesticides using in vitro reporter gene assays. Toxicology. 2011 Feb 27;280(3):77-87. doi: 10.1016/j.tox.2010.11.008. Epub 2010 Nov 27. [21115097 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated proinflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of ARNTL/BMAL1 in the blood vessels (By similarity).
- Gene Name:
- PPARG
- Uniprot ID:
- P37231
- Molecular Weight:
- 57619.58 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
- Gene Name:
- CYP2B6
- Uniprot ID:
- P20813
- Molecular Weight:
- 56277.81 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Transmembrane receptor protein tyrosine phosphatase activity
- Specific Function:
- Protein tyrosine-protein phosphatase required for T-cell activation through the antigen receptor. Acts as a positive regulator of T-cell coactivation upon binding to DPP4. The first PTPase domain has enzymatic activity, while the second one seems to affect the substrate specificity of the first one. Upon T-cell activation, recruits and dephosphorylates SKAP1 and FYN. Dephosphorylates LYN, and thereby modulates LYN activity (By similarity).
- Gene Name:
- PTPRC
- Uniprot ID:
- P08575
- Molecular Weight:
- 147253.075 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor isoform B (PRB) is involved activation of c-SRC/MAPK signaling on hormone stimulation.Isoform A: inactive in stimulating c-Src/MAPK signaling on hormone stimulation.Isoform 4: Increases mitochondrial membrane potential and cellular respiration upon stimulation by progesterone.
- Gene Name:
- PGR
- Uniprot ID:
- P06401
- Molecular Weight:
- 98979.96 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
- Gene Name:
- CYP2C19
- Uniprot ID:
- P33261
- Molecular Weight:
- 55930.545 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Transcription regulatory region dna binding
- Specific Function:
- Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
- Gene Name:
- AHR
- Uniprot ID:
- P35869
- Molecular Weight:
- 96146.705 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]