Butylparaben
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Basic Info
| Common Name | Butylparaben(F05179) |
| 2D Structure | |
| Description | Butylparaben is a preservative and flavouring agent. Butylparaben has been shown to exhibit anti-microbial function Butylparaben 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. (A3205). |
| FRCD ID | F05179 |
| CAS Number | 94-26-8 |
| PubChem CID | 7184 |
| Formula | C11H14O3 |
| IUPAC Name | butyl 4-hydroxybenzoate |
| InChI Key | QFOHBWFCKVYLES-UHFFFAOYSA-N |
| InChI | InChI=1S/C11H14O3/c1-2-3-8-14-11(13)9-4-6-10(12)7-5-9/h4-7,12H,2-3,8H2,1H3 |
| Canonical SMILES | CCCCOC(=O)C1=CC=C(C=C1)O |
| Isomeric SMILES | CCCCOC(=O)C1=CC=C(C=C1)O |
| Synonyms |
Butyl 4-hydroxybenzoate
Butyl chemosept
BUTYLPARABEN
94-26-8
Butyl paraben
Butyl p-hydroxybenzoate
Nipabutyl
Butoben
Butyl parasept
Butyl tegosept
|
| 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 | 194.23 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 5 |
| Complexity | 171 |
| Monoisotopic Mass | 194.094 |
| Exact Mass | 194.094 |
| XLogP | 3.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 14 |
| 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+ | 0.8116 |
| Human Intestinal Absorption | HIA+ | 0.9961 |
| Caco-2 Permeability | Caco2+ | 0.8661 |
| P-glycoprotein Substrate | Non-substrate | 0.5612 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9250 |
| Non-inhibitor | 0.9732 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8127 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8656 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7634 |
| CYP450 2D6 Substrate | Non-substrate | 0.8728 |
| CYP450 3A4 Substrate | Non-substrate | 0.6127 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.8820 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9070 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9288 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.7095 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9487 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8893 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9088 |
| Non-inhibitor | 0.9287 | |
| AMES Toxicity | Non AMES toxic | 0.9594 |
| Carcinogens | Non-carcinogens | 0.8284 |
| Fish Toxicity | High FHMT | 0.8388 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9622 |
| Honey Bee Toxicity | High HBT | 0.7611 |
| Biodegradation | Ready biodegradable | 0.9212 |
| Acute Oral Toxicity | III | 0.8010 |
| Carcinogenicity (Three-class) | Non-required | 0.5938 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.7827 | LogS |
| Caco-2 Permeability | 1.2109 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8426 | LD50, mol/kg |
| Fish Toxicity | 0.8615 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.4553 | 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 |
| 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 |
| Comparative toxic effects of butylparaben sodium, sodium diacetate and potassium sorbate to Dunaliella tertiolecta and HL7702 cells. | Food Funct | 2017 Dec 13 | 29090701 |
| Effects on the reproductive system of young male rats of subcutaneous exposure to n-butylparaben. | Food Chem Toxicol | 2017 Aug | 28526326 |
| Determination of paraben preservatives in seafood using matrix solid-phasedispersion and on-line acetylation gas chromatography-mass spectrometry. | J Chromatogr B Analyt Technol Biomed Life Sci | 2016 Nov 15 | 27736692 |
| Perinatal exposure to mixtures of endocrine disrupting chemicals reduces femalerat follicle reserves and accelerates reproductive aging. | Reprod Toxicol | 2016 Jun | 27049580 |
| Multiple Endocrine Disrupting Effects in Rats Perinatally Exposed toButylparaben. | Toxicol Sci | 2016 Jul | 27122241 |
| Ultrasound-assisted hydrolysis of conjugated parabens in human urine and theirdetermination by UPLC-MS/MS and UPLC-HRMS. | Anal Bioanal Chem | 2016 Feb | 26753983 |
| New method for the determination of parabens and bisphenol A in human milksamples using ultrasound-assisted extraction and clean-up with dispersivesorbents prior to UHPLC-MS/MS analysis. | J Chromatogr B Analyt Technol Biomed Life Sci | 2015 Jun 15 | 25942557 |
| 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 |
| Disruption of Sertoli cell vimentin filaments in prepubertal rats: an acuteeffect of butylparaben in vivo and in vitro. | Acta Histochem | 2014 Jun | 24444665 |
| Transesterification of a series of 12 parabens by liver and small-intestinalmicrosomes of rats and humans. | Food Chem Toxicol | 2014 Feb | 24355169 |
| Structure-activity relationship of a series of 17 parabens and related compounds for histamine release in rat peritoneal mast cells and skin allergic reaction in guinea pigs. | J Toxicol Sci | 2014 Feb | 24418712 |
| Simplified matrix solid phase dispersion procedure for the determination ofparabens and benzophenone-ultraviolet filters in human placental tissue samples. | J Chromatogr A | 2014 Dec 5 | 25456585 |
| 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 |
| Simultaneous derivatisation and preconcentration of parabens in food and othermatrices by isobutyl chloroformate and dispersive liquid-liquid microextractionfollowed by gas chromatographic analysis. | Food Chem | 2013 Nov 1 | 23768377 |
| Parabens enable suspension growth of MCF-10A immortalized, non-transformed human breast epithelial cells. | J Appl Toxicol | 2013 May | 22744862 |
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
- Witters H, Freyberger A, Smits K, Vangenechten C, Lofink W, Weimer M, Bremer S, Ahr PH, Berckmans P: The assessment of estrogenic or anti-estrogenic activity of chemicals by the human stably transfected estrogen sensitive MELN cell line: results of test performance and transferability. Reprod Toxicol. 2010 Aug;30(1):60-72. doi: 10.1016/j.reprotox.2010.02.008. Epub 2010 Mar 31. [20362049 ]
- General Function:
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- 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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
- Gene Name:
- CYP1A2
- Uniprot ID:
- P05177
- Molecular Weight:
- 58293.76 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:
- 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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
- Gene Name:
- CYP2C9
- Uniprot ID:
- P11712
- Molecular Weight:
- 55627.365 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:
- 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 ]