Ethylparaben
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Basic Info
| Common Name | Ethylparaben(F05177) |
| 2D Structure | |
| Description | Ethylparaben is found in alcoholic beverages. Ethylparaben is an antimicrobial agent, preservative. Ethylparaben is present in red wine, white wine and sake. Ethylparaben belongs to the family of Hydroxybenzoic Acid Derivatives. These are compounds containing an hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxylic acid. |
| FRCD ID | F05177 |
| CAS Number | 120-47-8 |
| PubChem CID | 8434 |
| Formula | C9H10O3 |
| IUPAC Name | ethyl 4-hydroxybenzoate |
| InChI Key | NUVBSKCKDOMJSU-UHFFFAOYSA-N |
| InChI | InChI=1S/C9H10O3/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6,10H,2H2,1H3 |
| Canonical SMILES | CCOC(=O)C1=CC=C(C=C1)O |
| Isomeric SMILES | CCOC(=O)C1=CC=C(C=C1)O |
| Wikipedia | Ethylparaben |
| Synonyms |
Ethyl p-hydroxybenzoate
Ethylparaben
ETHYL 4-HYDROXYBENZOATE
120-47-8
Ethyl paraben
Mycocten
Ethyl parasept
Easeptol
Ethyl butex
4-Hydroxybenzoic acid ethyl ester
|
| Classifies |
Predicted: Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Benzoic acids and derivatives |
| Intermediate Tree Nodes | Benzoic acid esters - p-Hydroxybenzoic acid esters |
| Direct Parent | p-Hydroxybenzoic acid alkyl esters |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | P-hydroxybenzoic acid alkyl ester - Benzoyl - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as p-hydroxybenzoic acid alkyl esters. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 166.176 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 3 |
| Complexity | 148 |
| Monoisotopic Mass | 166.063 |
| Exact Mass | 166.063 |
| XLogP | 2.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 12 |
| 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+ | 0.7623 |
| Human Intestinal Absorption | HIA+ | 0.9962 |
| Caco-2 Permeability | Caco2+ | 0.8866 |
| P-glycoprotein Substrate | Non-substrate | 0.6663 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9298 |
| Non-inhibitor | 0.9513 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8624 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.9320 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7745 |
| CYP450 2D6 Substrate | Non-substrate | 0.9123 |
| CYP450 3A4 Substrate | Non-substrate | 0.7058 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5392 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9528 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9700 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9016 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9721 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8670 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9456 |
| Non-inhibitor | 0.9622 | |
| AMES Toxicity | Non AMES toxic | 0.9434 |
| Carcinogens | Non-carcinogens | 0.7315 |
| Fish Toxicity | High FHMT | 0.7529 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9568 |
| Honey Bee Toxicity | High HBT | 0.8224 |
| Biodegradation | Ready biodegradable | 0.9063 |
| Acute Oral Toxicity | III | 0.8777 |
| Carcinogenicity (Three-class) | Non-required | 0.6027 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.2875 | LogS |
| Caco-2 Permeability | 1.0546 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.9148 | LD50, mol/kg |
| Fish Toxicity | 1.6309 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.6049 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Biodegradation of four selected parabens with aerobic activated sludge and their transesterification product. | Ecotoxicol Environ Saf | 2018 Jul 30 | 29529513 |
| Simultaneous determination of nine preservatives in food by liquid chromatographywith the aid of coagulant in the clean-up process. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2017May | 28277177 |
| Interference of Paraben Compounds with Estrogen Metabolism by Inhibition of17β-Hydroxysteroid Dehydrogenases. | Int J Mol Sci | 2017 Sep 19 | 28925944 |
| Regulatory risk assessments: Is there a need to reduce uncertainty and enhancerobustness? Update on propylparaben in relation to its EU regulatory status. | Hum Exp Toxicol | 2017 Oct | 28695774 |
| Preparation of magnetic graphene/mesoporous silica composites withphenyl-functionalized pore-walls as the restricted access matrix solid phaseextraction adsorbent for the rapid extraction of parabens from water-based skintoners. | J Chromatogr A | 2016 Sep 23 | 27575922 |
| The Combined Effect of Methyl- and Ethyl-Paraben on Lifespan and Preadult Development Period of Drosophila melanogaster (Diptera: Drosophilidae). | J Insect Sci | 2016 | 28076277 |
| Parabens in 24 h urine samples of the German Environmental Specimen Bank from1995 to 2012. | Int J Hyg Environ Health | 2015 Oct | 26253560 |
| "Parabenoia" Debunked, or "Who's Afraid of Parabens?". | Dermatitis | 2015 Nov-Dec | 26551603 |
| Rapid determination of parabens in seafood sauces by high-performance liquidchromatography: A practical comparison of core-shell particles and sub-2 μm fullyporous particles. | J Sep Sci | 2015 Dec | 26383987 |
| Antioxidant activity of penta-oligogalacturonide, isolated from haw pectin,suppresses triglyceride synthesis in mice fed with a high-fat diet. | Food Chem | 2014 Feb 15 | 24128486 |
| Widespread occurrence of bisphenol A diglycidyl ethers, p-hydroxybenzoic acidesters (parabens), benzophenone type-UV filters, triclosan, and triclocarban inhuman urine from Athens, Greece. | Sci Total Environ | 2014 Feb 1 | 24246946 |
| Potassium bromate causes cell lysis and induces oxidative stress in humanerythrocytes. | Environ Toxicol | 2014 Feb | 22012894 |
| Ethylparaben affects lifespan, fecundity, and the expression levels of ERR, EcR and YPR in Drosophila melanogaster. | J Insect Physiol | 2014 Dec | 25265034 |
| Exposure determinants of phthalates, parabens, bisphenol A and triclosan in Swedish mothers and their children. | Environ Int | 2014 Dec | 25216151 |
| Histochemical visualization of ROS and antioxidant response to viral infectionsof vegetable crops grown in Azerbaijan. | Plant Physiol Biochem | 2014 Aug | 24661407 |
| The hepatoprotection of caffeic acid and rosmarinic acid, major compounds ofPerilla frutescens, against t-BHP-induced oxidative liver damage. | Food Chem Toxicol | 2013 May | 23306788 |
| Modulatory effects of dietary inclusion of garlic (Allium sativum) ongentamycin-induced hepatotoxicity and oxidative stress in rats. | Asian Pac J Trop Biomed | 2013 Jun | 23730560 |
| Occurrence of parabens in foodstuffs from China and its implications for humandietary exposure. | Environ Int | 2013 Jul | 23685225 |
| Effects of parabens on adipocyte differentiation. | Toxicol Sci | 2013 Jan | 22956630 |
| Effects of dietary isoleucine on the immune response, antioxidant status and geneexpression in the head kidney of juvenile Jian carp (Cyprinus carpio var. Jian). | Fish Shellfish Immunol | 2013 Aug | 23742869 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide.
- Gene Name:
- CA7
- Uniprot ID:
- P43166
- Molecular Weight:
- 29658.235 Da
References
- Carta F, Vullo D, Maresca A, Scozzafava A, Supuran CT: Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15;21(6):1564-9. doi: 10.1016/j.bmc.2012.05.019. Epub 2012 May 17. [22668600 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
References
- Watanabe Y, Kojima H, Takeuchi S, Uramaru N, Ohta S, Kitamura S: Comparative study on transcriptional activity of 17 parabens mediated by estrogen receptor alpha and beta and androgen receptor. Food Chem Toxicol. 2013 Jul;57:227-34. doi: 10.1016/j.fct.2013.03.036. Epub 2013 Apr 6. [23567241 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
- Gene Name:
- CA1
- Uniprot ID:
- P00915
- Molecular Weight:
- 28870.0 Da
References
- Carta F, Vullo D, Maresca A, Scozzafava A, Supuran CT: Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15;21(6):1564-9. doi: 10.1016/j.bmc.2012.05.019. Epub 2012 May 17. [22668600 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide.
- Gene Name:
- CA12
- Uniprot ID:
- O43570
- Molecular Weight:
- 39450.615 Da
References
- Carta F, Vullo D, Maresca A, Scozzafava A, Supuran CT: Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15;21(6):1564-9. doi: 10.1016/j.bmc.2012.05.019. Epub 2012 May 17. [22668600 ]
- General Function:
- Metal ion binding
- Specific Function:
- Reversible hydration of carbon dioxide.
- Gene Name:
- CA14
- Uniprot ID:
- Q9ULX7
- Molecular Weight:
- 37667.37 Da
References
- Carta F, Vullo D, Maresca A, Scozzafava A, Supuran CT: Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15;21(6):1564-9. doi: 10.1016/j.bmc.2012.05.019. Epub 2012 May 17. [22668600 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion into the anterior chamber of the eye. Contributes to intracellular pH regulation in the duodenal upper villous epithelium during proton-coupled peptide absorption. Stimulates the chloride-bicarbonate exchange activity of SLC26A6.
- Gene Name:
- CA2
- Uniprot ID:
- P00918
- Molecular Weight:
- 29245.895 Da
References
- Carta F, Vullo D, Maresca A, Scozzafava A, Supuran CT: Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15;21(6):1564-9. doi: 10.1016/j.bmc.2012.05.019. Epub 2012 May 17. [22668600 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide. Participates in pH regulation. May be involved in the control of cell proliferation and transformation. Appears to be a novel specific biomarker for a cervical neoplasia.
- Gene Name:
- CA9
- Uniprot ID:
- Q16790
- Molecular Weight:
- 49697.36 Da
References
- Carta F, Vullo D, Maresca A, Scozzafava A, Supuran CT: Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15;21(6):1564-9. doi: 10.1016/j.bmc.2012.05.019. Epub 2012 May 17. [22668600 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
- Gene Name:
- ESR2
- Uniprot ID:
- Q92731
- Molecular Weight:
- 59215.765 Da
References
- Watanabe Y, Kojima H, Takeuchi S, Uramaru N, Ohta S, Kitamura S: Comparative study on transcriptional activity of 17 parabens mediated by estrogen receptor alpha and beta and androgen receptor. Food Chem Toxicol. 2013 Jul;57:227-34. doi: 10.1016/j.fct.2013.03.036. Epub 2013 Apr 6. [23567241 ]