Propylparaben
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Basic Info
| Common Name | Propylparaben(F05178) |
| 2D Structure | |
| Description | Propylparaben is an antimicrobial agent, preservative, flavouring agent. Propylparaben 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 | F05178 |
| CAS Number | 94-13-3 |
| PubChem CID | 7175 |
| Formula | C10H12O3 |
| IUPAC Name | propyl 4-hydroxybenzoate |
| InChI Key | QELSKZZBTMNZEB-UHFFFAOYSA-N |
| InChI | InChI=1S/C10H12O3/c1-2-7-13-10(12)8-3-5-9(11)6-4-8/h3-6,11H,2,7H2,1H3 |
| Canonical SMILES | CCCOC(=O)C1=CC=C(C=C1)O |
| Isomeric SMILES | CCCOC(=O)C1=CC=C(C=C1)O |
| Synonyms |
94-13-3
Propyl Butex
Propyl 4-hydroxybenzoate
PROPYLPARABEN
Propyl paraben
4-Hydroxybenzoic acid propyl ester
Propyl p-hydroxybenzoate
Nipasol
Nipazol
Betacide P
|
| 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 | 180.203 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 4 |
| Complexity | 160 |
| Monoisotopic Mass | 180.079 |
| Exact Mass | 180.079 |
| XLogP | 3 |
| Formal Charge | 0 |
| Heavy Atom Count | 13 |
| 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+ | 0.8048 |
| Human Intestinal Absorption | HIA+ | 0.9955 |
| Caco-2 Permeability | Caco2+ | 0.8663 |
| P-glycoprotein Substrate | Non-substrate | 0.6327 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9050 |
| Non-inhibitor | 0.9572 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8374 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8806 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7784 |
| CYP450 2D6 Substrate | Non-substrate | 0.8839 |
| CYP450 3A4 Substrate | Non-substrate | 0.6157 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.7756 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9119 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9411 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.5806 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9631 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8925 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8877 |
| Non-inhibitor | 0.9354 | |
| AMES Toxicity | Non AMES toxic | 0.9686 |
| Carcinogens | Non-carcinogens | 0.8166 |
| Fish Toxicity | High FHMT | 0.6508 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9767 |
| Honey Bee Toxicity | High HBT | 0.7643 |
| Biodegradation | Ready biodegradable | 0.9390 |
| Acute Oral Toxicity | III | 0.8523 |
| Carcinogenicity (Three-class) | Non-required | 0.5469 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.3823 | LogS |
| Caco-2 Permeability | 1.2293 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8885 | LD50, mol/kg |
| Fish Toxicity | 1.1549 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.2617 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Photolysis of parabens using medium-pressure mercury lamps: Toxicity effects in MCF7, Balb/c 3T3 cells and Ceriodaphnia dubia. | Chemosphere | 2018 Oct | 29885499 |
| Biodegradation of four selected parabens with aerobic activated sludge and their transesterification product. | Ecotoxicol Environ Saf | 2018 Jul 30 | 29529513 |
| Electrospun polystyrene fibers knitted around imprinted acrylate microspheres as sorbent for paraben derivatives. | Anal Chim Acta | 2018 Jul 19 | 29523246 |
| 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 |
| 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 |
| In vitro skin absorption tests of three types of parabens using a Franz diffusioncell. | J Expo Sci Environ Epidemiol | 2017 May | 27436697 |
| Poly(styrene-co-N-methacryloyl-l-phenylalanine methyl ester)-functionalizedmagnetic nanoparticles as sorbents for the analysis of sodium benzoate inbeverages. | J Sep Sci | 2017 Jan | 27863035 |
| Anticonvulsant effect of sodium cyclamate and propylparaben onpentylenetetrazol-induced seizures in zebrafish. | Synapse | 2017 Apr | 28118493 |
| 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 |
| Propylparaben reduces the excitability of hippocampal neurons by blocking sodium channels. | Neurotoxicology | 2016 Dec | 27693446 |
| Regulatory risk assessments: Is there a need to reduce uncertainty and enhancerobustness? | Hum Exp Toxicol | 2015 Dec | 26614814 |
| 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 |
| The antioxidant butylated hydroxyanisole potentiates the toxic effects of propylparaben in cultured mammalian cells. | Food Chem Toxicol | 2014 Oct | 25086368 |
| The associations of triclosan and paraben exposure with allergen sensitizationand wheeze in children. | Allergy Asthma Proc | 2014 Nov-Dec | 25584915 |
| Antimicrobial and antibiofilm effects of selected food preservatives againstSalmonella spp. isolated from chicken samples. | Poult Sci | 2014 Mar | 24604864 |
| Embryonic exposure of medaka (Oryzias latipes) to propylparaben: effects on early development and post-hatching growth. | Environ Pollut | 2014 Jan | 24095706 |
| Bioanalysis of propylparaben and p-hydroxybenzoic acid, and their sulfateconjugates in rat plasma by liquid chromatography-tandem mass spectrometry. | J Chromatogr B Analyt Technol Biomed Life Sci | 2014 Feb 1 | 24412689 |
| 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 |
| Urinary concentrations of environmental phenols in pregnant women in a pilotstudy of the National Children's Study. | Environ Res | 2014 Feb | 24529000 |
| Transesterification of a series of 12 parabens by liver and small-intestinalmicrosomes of rats and humans. | Food Chem Toxicol | 2014 Feb | 24355169 |
Targets
- 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:
- 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 ]
- 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 ]