T3DB: Propylparaben

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (3)XML

Targets (3)

Record Information

Version

2.0

Creation Date

2014-08-29 04:48:30 UTC

Update Date

2014-12-24 20:26:35 UTC

Accession Number

T3D3979

Identification

Common Name

Propylparaben

Class

Small Molecule

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.

Compound Type

Ester
Ether
Flavouring Agent
Food Toxin
Household Toxin
Industrial/Workplace Toxin
Metabolite
Organic Compound
Preservative
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym
4-Hydroxybenzoic acid propyl ester
4-Hydroxybenzoic acid propylester
4-Hydroxybenzoic acid, propyl ester
Aseptoform p
Benzoic acid, 4-hydroxy-, propyl ester
Benzoic acid, p-hydroxy-, propyl ester
Betacide p
Betacine p
Chemacide PK
Chemocide PK
Chemoside PK
Lexgard p
N-Propyl 4-hydroxybenzoate
N-Propyl p-hydroxybenzoate
N-Propyl-p-hydroxybenzoate
N-Propylparaben
Nipagin p
Nipasol
P-Hydroxybenzoic acid N-propyl ester
P-Hydroxybenzoic acid propyl ester
P-Hydroxybenzoic acid, propyl ester
P-Hydroxybenzoic propyl ester
P-Hydroxypropyl benzoate
Propagin
Propyl 4-hydroxybenzoate
Propyl aseptoform
Propyl butex
Propyl chemosept
Propyl chemsept
Propyl p-hydroxybenzoate
Propyl paraben
Propyl parahydroxybenzoate
Propyl parasept
Propyl-4-hydroxybenzoate
Propyl-paraben
Propylparaben, USAN
Propylparasept
Protaben p
Solbrol P
Tegosept p

Chemical Formula

C₁₀H₁₂O₃

Average Molecular Mass

180.201 g/mol

Monoisotopic Mass

180.079 g/mol

CAS Registry Number

94-13-3

IUPAC Name

propyl 4-hydroxybenzoate

Traditional Name

propylparaben

SMILES

CCCOC(=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C10H12O3/c1-2-7-13-10(12)8-3-5-9(11)6-4-8/h3-6,11H,2,7H2,1H3

InChI Key

InChIKey=QELSKZZBTMNZEB-UHFFFAOYSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

p-Hydroxybenzoic acid alkyl esters

Alternative Parents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:32063 )
benzoate ester (CHEBI:32063 )
paraben (CHEBI:32063 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	96 - 97°C
Boiling Point	Not Available
Solubility	0.5 mg/mL at 25°C
LogP	3.04

Predicted Properties

Property	Value	Source
Water Solubility	0.96 g/L	ALOGPS
logP	3.28	ALOGPS
logP	2.55	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	8.5	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	49.34 m³·mol⁻¹	ChemAxon
Polarizability	19.35 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00dr-2900000000-5ad831b2650fc930116c	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00dr-2900000000-5ad831b2650fc930116c	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-4900000000-ea56320d2db779d7b4ba	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0006-3910000000-6627fe49566ac19f2646	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004i-0900000000-a528bf6bd610eaa4d56d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-004i-0900000000-a528bf6bd610eaa4d56d	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0079-0900000000-f8b4d22e11212406a669	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-c2e531f56db73c6d33e8	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00di-0900000000-3687d6281f4f012f14a8	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0900000000-cc364f1a508151d37b72	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-04f2ce573f4ba08b5bc8	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-32ccfdbd83a4d2db7d8b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9000000000-57094c48887cb16375a4	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-2900000000-f3c11565fcd12f9e860b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-004r-0900000000-f3bacac2e75bf5f75e20	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-000l-4900000000-a177f5dd4882f3644ebc	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-002b-9400000000-9bab2a6dfc09b743ab7e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-33c4bb8f3aa111e3c3aa	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-cae53eb5d810f1eb49c7	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9200000000-0217e404cbb1450be5b2	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0079-0900000000-75d92497c0382dfbecd5	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-052f-9200000000-9b90e1d540d5b83dcbc2	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-052f-9200000000-fd8218d9ad65ba82afca	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-2900000000-4ca188f06fa4b53e3248	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-9600000000-5d01c0904ab22d191c71	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9300000000-13a8f8a6fa20b2a61dd8	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-1900000000-c039bed96e2f85d3b72c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000l-3900000000-476bdcb3573067826dc1	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9400000000-7a7313c9b1e989f7c4dc	2016-08-03	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00dr-4900000000-1b9740067a9969c2e70d	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

Not Available

UniProt ID

Not Available

OMIM ID

ChEBI ID

32063

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

T3D3979.pdf

General References

Jadach M, Blazewicz A, Fijalek Z: Determination of local anesthetics in illegal products using HPLC method with amperometric detection. Acta Pol Pharm. 2012 May-Jun;69(3):397-403. [22594253 ]
Chen ZF, Ying GG, Lai HJ, Chen F, Su HC, Liu YS, Peng FQ, Zhao JL: Determination of biocides in different environmental matrices by use of ultra-high-performance liquid chromatography-tandem mass spectrometry. Anal Bioanal Chem. 2012 Dec;404(10):3175-88. doi: 10.1007/s00216-012-6444-2. Epub 2012 Oct 10. [23052884 ]
Albero B, Perez RA, Sanchez-Brunete C, Tadeo JL: Occurrence and analysis of parabens in municipal sewage sludge from wastewater treatment plants in Madrid (Spain). J Hazard Mater. 2012 Nov 15;239-240:48-55. doi: 10.1016/j.jhazmat.2012.05.017. Epub 2012 May 11. [22640822 ]
Harvey PW, Everett DJ: Parabens detection in different zones of the human breast: consideration of source and implications of findings. J Appl Toxicol. 2012 May;32(5):305-9. doi: 10.1002/jat.2743. Epub 2012 Mar 7. [22408000 ]
Perez-Lozano P, Garcia-Montoya E, Orriols A, Minarro M, Tico JR, Sune-Negre JM: A new validated method for the simultaneous determination of benzocaine, propylparaben and benzyl alcohol in a bioadhesive gel by HPLC. J Pharm Biomed Anal. 2005 Oct 4;39(5):920-7. Epub 2005 Jul 20. [16039086 ]
Yu K, Li B, Zhang T: Direct rapid analysis of multiple PPCPs in municipal wastewater using ultrahigh performance liquid chromatography-tandem mass spectrometry without SPE pre-concentration. Anal Chim Acta. 2012 Aug 13;738:59-68. doi: 10.1016/j.aca.2012.05.057. Epub 2012 Jun 9. [22790701 ]
Hu P, Chen X, Whitener RJ, Boder ET, Jones JO, Porollo A, Chen J, Zhao L: Effects of parabens on adipocyte differentiation. Toxicol Sci. 2013 Jan;131(1):56-70. doi: 10.1093/toxsci/kfs262. Epub 2012 Sep 5. [22956630 ]
Gurtler JB, Jin TZ: Propylparaben sensitizes heat-resistant Salmonella Enteritidis and Salmonella Oranienburg to thermal inactivation in liquid egg albumen. J Food Prot. 2012 Mar;75(3):443-8. doi: 10.4315/0362-028X.JFP-11-158. [22410216 ]
Dvores MP, Marom G, Magdassi S: Formation of organic nanoparticles by electrospinning of volatile microemulsions. Langmuir. 2012 May 1;28(17):6978-84. doi: 10.1021/la204741f. Epub 2012 Apr 19. [22452574 ]
Talevi A, Bellera CL, Castro EA, Bruno-Blanch LE: A successful virtual screening application: prediction of anticonvulsant activity in MES test of widely used pharmaceutical and food preservatives methylparaben and propylparaben. J Comput Aided Mol Des. 2007 Sep;21(9):527-38. Epub 2007 Oct 25. [17960329 ]
Lee T, Lok C, Vazquez M, Moist L, Maya I, Mokrzycki M: Minimizing hemodialysis catheter dysfunction: an ounce of prevention. Int J Nephrol. 2012;2012:170857. doi: 10.1155/2012/170857. Epub 2012 Feb 19. [22518310 ]
Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Estrogen receptor

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

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	4.20 uM	ACEA_T47D_80hr_Positive	ACEA Biosciences
AC50	9.43 uM	ATG_ERE_CIS	Attagene
AC50	4.68 uM	NVS_NR_hER	Novascreen

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 ]
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 ]

Target Details

2. Estrogen receptor beta

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

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	6.97 uM	OT_ER_ERbERb_0480	Odyssey Thera
AC50	8.02 uM	OT_ER_ERbERb_1440	Odyssey Thera

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 ]
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 ]

Target Details

3. Peroxisome proliferator-activated receptor gamma

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 ]

Propylparaben (T3D3979)

Structure for T3D3979: Propylparaben

Targets

Binding/Activity Constants

References

Binding/Activity Constants

References

References