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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 17:50:35 UTC
Update Date2019-07-23 06:11:17 UTC
HMDB IDHMDB0032575
Secondary Accession Numbers
  • HMDB32575
Metabolite Identification
Common NameButylparaben
DescriptionButylparaben, also known as butyl par asept or tegosept b, 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. Butylparaben displayed the most competitive binding to rat estrogen receptors when tested along with methyl, ethyl, and propylparabens. Butylparaben is an extremely weak basic (essentially neutral) compound (based on its pKa). Butylparaben is a very faint and phenolic tasting compound. Butylparaben is a potentially toxic compound. However, parabens have not been proven to cause breast cancer. It has been used in cosmetic products since the 1940s and in pharmaceutical products since 1924.
Structure
Data?1563862277
Synonyms
ValueSource
4-(Butoxycarbonyl)phenolHMDB
4-Hydroxybenzoic acid butyl esterHMDB
4-Hydroxybenzoic acid, butyl esterHMDB
Aseptoform butylHMDB
Benzoic acid, 4-hydroxy-, butyl esterHMDB
Benzoic acid, p-hydroxy-, butyl esterHMDB
ButobenHMDB
Butyl //p//-hydroxybenzoateHMDB
Butyl 4-hydroxybenzoateHMDB
Butyl butexHMDB
Butyl chemoseptHMDB
Butyl p-hydroxybenzoateHMDB
Butyl par aseptHMDB
Butyl parabenHMDB
Butyl parahydroxybenzoateHMDB
Butyl parahydroxybenzoate (JP15)HMDB
Butyl paraseptHMDB
Butyl tegoseptHMDB
Butyl-p-hydroxybenzoateHMDB
Butyl-paraseptHMDB
Butylparaben (NF)HMDB
FEMA 2203HMDB
Lexgard bHMDB
N-Butyl 4-hydroxybenzoateHMDB
N-Butyl hydroxybenzoateHMDB
N-Butyl p-hydroxybenzoateHMDB
N-Butyl parabenHMDB
N-Butyl parahydroxybenzoateHMDB
N-Butyl-4-hydroxybenzoateHMDB
N-Butyl-p-hydroxybenzoateHMDB
N-Butyl-parabenHMDB
NipabutylHMDB
p-Hydroxy butyl benzoateHMDB
p-Hydroxybenzoic acid butyl esterHMDB
p-Hydroxybenzoic acid N-butyl esterHMDB
p-Hydroxybenzoic acid, butyl esterHMDB
p-Hydroxybenzoic butyl esterHMDB
ParaseptHMDB
Preserval bHMDB
Solbrol bHMDB
SPFHMDB
Tegosept bHMDB
Tegosept butylHMDB
ButylparabenKEGG
Butyl parahydroxybenzoic acidGenerator
Chemical FormulaC11H14O3
Average Molecular Weight194.2271
Monoisotopic Molecular Weight194.094294314
IUPAC Namebutyl 4-hydroxybenzoate
Traditional Namebutylparaben
CAS Registry Number94-26-8
SMILES
CCCCOC(=O)C1=CC=C(O)C=C1
InChI Identifier
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
InChI KeyQFOHBWFCKVYLES-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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point68 - 69 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.21 mg/mL at 20 °CNot Available
LogP3.57Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.47 g/LALOGPS
logP3.81ALOGPS
logP3ChemAxon
logS-2.6ALOGPS
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 Count5ChemAxon
Refractivity53.94 m³·mol⁻¹ChemAxon
Polarizability21.45 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dr-2900000000-bb56a149a6da74d93ee8Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0079-3900000000-3c58d2a06f7053d6232cSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dr-2900000000-bb56a149a6da74d93ee8Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0079-3900000000-3c58d2a06f7053d6232cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-5900000000-a07eb5ffe2dd5224cc42Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-4900000000-b50d93adc6a9e391c467Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0900000000-e5adfc9cf6eccf247f8aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0900000000-2b574dc259808331afc7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-1900000000-831ef1d350d13780a329Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-1900000000-ce6d6917117d7a334d95Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-0900000000-56813e9a5bacca3c57f9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0900000000-e5adfc9cf6eccf247f8aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0900000000-2b574dc259808331afc7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-1900000000-831ef1d350d13780a329Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-1900000000-ce6d6917117d7a334d95Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0072-9800000000-fe4706758a9d399987b9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-9500000000-8c7830a4583c649d2753Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-4981588a915a613086d0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-a1bc78b908d3b7a1fb17Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0072-9800000000-fe4706758a9d399987b9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-9500000000-8c7830a4583c649d2753Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-4981588a915a613086d0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-a1bc78b908d3b7a1fb17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-2900000000-5c2e16e5df0c1640445aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9600000000-d8a6a3f37504b01c3773Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abc-9200000000-df6492b55ad6172bd44fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1900000000-aec24ddd4de8f43b0a06Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-3900000000-ef4eb95372bf56bcd294Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9400000000-34d1624c244b2672ad38Spectrum
MSMass Spectrum (Electron Ionization)splash10-00dr-3900000000-0366956a08d3509a13f7Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.000483 (0.000373-0.000693) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
details
UrineDetected and Quantified0.00124 (0.00110-0.00145) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB010512
KNApSAcK IDNot Available
Chemspider ID6916
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkButylparaben
METLIN IDNot Available
PubChem Compound7184
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Qian L, Guan Y, Xiao H: Preparation and characterization of inclusion complexes of a cationic beta-cyclodextrin polymer with butylparaben or triclosan. Int J Pharm. 2008 Jun 5;357(1-2):244-51. doi: 10.1016/j.ijpharm.2008.01.018. Epub 2008 Jan 19. [PubMed:18294789 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .