Propylparaben (CHEM002939)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (3)XML
Record Information
Version1.0
Creation Date2014-08-29 04:48:30 UTC
Update Date2026-05-14 19:41:44 UTC
Accession NumberCHEM002939
Identification
Common NamePropylparaben
ClassSmall Molecule
DescriptionPropylparaben 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.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Ether
  • Flavouring Agent
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Preservative
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
4-Hydroxybenzoic acid propyl esterChEBI
4-Hydroxybenzoic acid, propyl esterChEBI
N-Propyl 4-hydroxybenzoateChEBI
N-Propyl p-hydroxybenzoateChEBI
N-Propyl parabenChEBI
p-Hydroxybenzoic acid propyl esterChEBI
p-Hydroxybenzoic propyl esterChEBI
p-Hydroxypropyl benzoateChEBI
p-OxybenzoesaeurepropylesterChEBI
Propyl p-hydroxybenzoateChEBI
Propyl parabenChEBI
Propyl parahydroxybenzoateChEBI
4-Hydroxybenzoate propyl esterGenerator
4-Hydroxybenzoate, propyl esterGenerator
N-Propyl 4-hydroxybenzoic acidGenerator
N-Propyl p-hydroxybenzoic acidGenerator
p-Hydroxybenzoate propyl esterGenerator
p-Hydroxypropyl benzoic acidGenerator
Propyl p-hydroxybenzoic acidGenerator
Propyl parahydroxybenzoic acidGenerator
3(Or 4)-hydroxybenzoic acid propyl esterMeSH
NipazolMeSH
Propyl 4-hydroxybenzoateMeSH
Propylparaben, monosodium saltMeSH
Bayer D 206MeSH
PEPHMeSH
4-Hydroxybenzoic acid propylesterHMDB
Aseptoform PHMDB
Benzoic acid, 4-hydroxy-, propyl esterHMDB
Benzoic acid, P-hydroxy-, propyl esterHMDB
Betacide PHMDB
Betacine PHMDB
Chemacide PKHMDB
Chemocide PKHMDB
Chemoside PKHMDB
Lexgard PHMDB
N-Propyl-P-hydroxybenzoateHMDB
N-PropylparabenHMDB
Nipagin PHMDB
NipasolHMDB
P-Hydroxybenzoic acid N-propyl esterHMDB
P-Hydroxybenzoic acid, propyl esterHMDB
PropaginHMDB
Propyl aseptoformHMDB
Propyl butexHMDB
Propyl chemoseptHMDB
Propyl chemseptHMDB
Propyl paraseptHMDB
Propyl-4-hydroxybenzoateHMDB
Propyl-parabenHMDB
Propylparaben, usanHMDB
PropylparaseptHMDB
Protaben PHMDB
Solbrol PHMDB
Tegosept PHMDB
Chemical FormulaC10H12O3
Average Molecular Mass180.201 g/mol
Monoisotopic Mass180.079 g/mol
CAS Registry Number94-13-3
IUPAC Namepropyl 4-hydroxybenzoate
Traditional Namepropylparaben
SMILESCCCOC(=O)C1=CC=C(O)C=C1
InChI IdentifierInChI=1S/C10H12O3/c1-2-7-13-10(12)8-3-5-9(11)6-4-8/h3-6,11H,2,7H2,1H3
InChI KeyQELSKZZBTMNZEB-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct Parentp-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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point96 - 97°C
Boiling PointNot Available
Solubility0.5 mg/mL at 25°C
Predicted Properties
PropertyValueSource
Water Solubility0.96 g/LALOGPS
logP3.28ALOGPS
logP2.55ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)8.5ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity49.34 m³·mol⁻¹ChemAxon
Polarizability19.35 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dr-2900000000-5ad831b2650fc930116cSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dr-2900000000-5ad831b2650fc930116cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-4900000000-ea56320d2db779d7b4baSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-3910000000-6627fe49566ac19f2646Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-0900000000-a528bf6bd610eaa4d56dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-004i-0900000000-a528bf6bd610eaa4d56dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0079-0900000000-f8b4d22e11212406a669Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-c2e531f56db73c6d33e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00di-0900000000-3687d6281f4f012f14a8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00di-0900000000-cc364f1a508151d37b72Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-04f2ce573f4ba08b5bc8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-32ccfdbd83a4d2db7d8bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-57094c48887cb16375a4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-2900000000-f3c11565fcd12f9e860bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004r-0900000000-f3bacac2e75bf5f75e20Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-000l-4900000000-a177f5dd4882f3644ebcSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-002b-9400000000-9bab2a6dfc09b743ab7eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-33c4bb8f3aa111e3c3aaSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-cae53eb5d810f1eb49c7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-9200000000-0217e404cbb1450be5b2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0079-0900000000-75d92497c0382dfbecd5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-052f-9200000000-9b90e1d540d5b83dcbc2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-052f-9200000000-fd8218d9ad65ba82afcaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-2900000000-4ca188f06fa4b53e3248Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9600000000-5d01c0904ab22d191c71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-13a8f8a6fa20b2a61dd8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-c039bed96e2f85d3b72cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-3900000000-476bdcb3573067826dc1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-7a7313c9b1e989f7c4dcSpectrum
MSMass Spectrum (Electron Ionization)splash10-00dr-4900000000-1b9740067a9969c2e70dSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0032574
FooDB IDFDB010511
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPropylparaben
Chemspider ID6907
ChEBI ID32063
PubChem Compound ID7175
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21492176
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21549034
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21608130
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21645663
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21705745
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21886901
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22165009
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22177019
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22220814
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22237600
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22249112
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22305363
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22337803
14. 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.
15. 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.
16. 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.
17. 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.
18. 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.
19. 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.
20. 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.
21. 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.
22. 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.
23. 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.
24. 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.
25. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.