Methylparaben
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Basic Info
| Common Name | Methylparaben(F05176) |
| 2D Structure | |
| Description | Methylparaben is found in alcoholic beverages. Methylparaben is an antimicrobial agent, preservative, flavouring agent. Methylparaben is a constituent of cloudberry, yellow passion fruit, white wine, botrytised wine and Bourbon vanilla. Methylparaben has been shown to exhibit anti-microbial function Methylparaben 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. (A3204). |
| FRCD ID | F05176 |
| CAS Number | 99-76-3 |
| PubChem CID | 7456 |
| Formula | C8H8O3 |
| IUPAC Name | methyl 4-hydroxybenzoate |
| InChI Key | LXCFILQKKLGQFO-UHFFFAOYSA-N |
| InChI | InChI=1S/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3 |
| Canonical SMILES | COC(=O)C1=CC=C(C=C1)O |
| Isomeric SMILES | COC(=O)C1=CC=C(C=C1)O |
| Synonyms |
Methyl p-hydroxybenzoate
Methyl 4-hydroxybenzoate
METHYLPARABEN
99-76-3
Methyl paraben
Nipagin
Methyl parahydroxybenzoate
Maseptol
p-Hydroxybenzoic acid methyl ester
p-Carbomethoxyphenol
|
| Classifies |
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 - Methyl ester - 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 | 152.149 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 2 |
| Complexity | 136 |
| Monoisotopic Mass | 152.047 |
| Exact Mass | 152.047 |
| XLogP | 2 |
| Formal Charge | 0 |
| Heavy Atom Count | 11 |
| 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+ | 0.7427 |
| Human Intestinal Absorption | HIA+ | 0.9887 |
| Caco-2 Permeability | Caco2+ | 0.8682 |
| P-glycoprotein Substrate | Non-substrate | 0.7105 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9617 |
| Non-inhibitor | 0.9644 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8791 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.9255 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7458 |
| CYP450 2D6 Substrate | Non-substrate | 0.9172 |
| CYP450 3A4 Substrate | Non-substrate | 0.6947 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6776 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9764 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9848 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9503 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9761 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9640 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9493 |
| Non-inhibitor | 0.9791 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.8321 |
| Fish Toxicity | High FHMT | 0.7015 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8900 |
| Honey Bee Toxicity | High HBT | 0.8502 |
| Biodegradation | Ready biodegradable | 0.8781 |
| Acute Oral Toxicity | III | 0.8243 |
| Carcinogenicity (Three-class) | Non-required | 0.5851 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.8579 | LogS |
| Caco-2 Permeability | 1.1158 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8917 | LD50, mol/kg |
| Fish Toxicity | 1.9309 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.0748 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Methylparaben induces malformations and alterations on apoptosis, oxidant-antioxidant status, ccnd1 and myca expressions in zebrafish embryos. | J Biochem Mol Toxicol | 2018 Mar | 29360218 |
| Biodegradation of four selected parabens with aerobic activated sludge and their transesterification product. | Ecotoxicol Environ Saf | 2018 Jul 30 | 29529513 |
| Methylparaben-induced decrease in collagen production and viability of culturedhuman dermal fibroblasts. | J Appl Toxicol | 2017 Sep | 28382686 |
| Environmental exposure to parabens and sperm chromosome disomy. | Int J Environ Health Res | 2017 Oct | 28609180 |
| Photosensitized methyl paraben induces apoptosis via caspase dependent pathwayunder ambient UVB exposure in human skin cells. | Food Chem Toxicol | 2017 Oct | 28764904 |
| In vitro skin absorption tests of three types of parabens using a Franz diffusioncell. | J Expo Sci Environ Epidemiol | 2017 May | 27436697 |
| Trophic Magnification of Parabens and Their Metabolites in a Subtropical MarineFood Web. | Environ Sci Technol | 2017 Jan 17 | 27959523 |
| Paraben Concentrations in Maternal Urine and Breast Milk and Its Association withPersonal Care Product Use. | Environ Sci Technol | 2017 Apr 4 | 28318231 |
| 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 |
| Impact of microbial growth inhibition and proteolytic activity on the stabilityof a new formulation containing a phytate-degrading enzyme obtained frommushroom. | Prep Biochem Biotechnol | 2016 Oct 2 | 26760722 |
| Metabolism and elimination of methyl, iso- and n-butyl paraben in human urineafter single oral dosage. | Arch Toxicol | 2016 Nov | 26608183 |
| Matrix solid-phase dispersion combined to liquid chromatography-tandem massspectrometry for the determination of paraben preservatives in mollusks. | J Chromatogr A | 2016 Aug 12 | 27401811 |
| 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 |
| Influence of fat addition on the antimicrobial activity of sodium lactate, lauricarginate and methylparaben in minced meat. | Int J Food Microbiol | 2015 Dec 23 | 26344644 |
| 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 |
| Development of a multianalyte method based on micro-matrix-solid-phase dispersionfor the analysis of fragrance allergens and preservatives in personal careproducts. | J Chromatogr A | 2014 May 30 | 24767833 |
| Prevalence of sensitivity to food and drug additives in patients with chronicidiopathic urticaria. | J Allergy Clin Immunol Pract | 2014 Mar-Apr | 24607044 |
| Antimicrobial and antibiofilm effects of selected food preservatives againstSalmonella spp. isolated from chicken samples. | Poult Sci | 2014 Mar | 24604864 |
Targets
- 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:
- 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:
- 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:
- 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:
- Xanthine oxidase activity
- Specific Function:
- Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
- Gene Name:
- XDH
- Uniprot ID:
- P47989
- Molecular Weight:
- 146422.99 Da
References
- Cioffi G, D'Auria M, Braca A, Mendez J, Castillo A, Morelli I, De Simone F, De Tommasi N: Antioxidant and free-radical scavenging activity of constituents of the leaves of Tachigalia paniculata. J Nat Prod. 2002 Nov;65(11):1526-9. [12444671 ]
- 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:
- 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
- Pereira-Fernandes A, Demaegdt H, Vandermeiren K, Hectors TL, Jorens PG, Blust R, Vanparys C: Evaluation of a screening system for obesogenic compounds: screening of endocrine disrupting compounds and evaluation of the PPAR dependency of the effect. PLoS One. 2013 Oct 14;8(10):e77481. doi: 10.1371/journal.pone.0077481. eCollection 2013. [24155963 ]