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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:50:35 UTC
Update Date2022-03-07 02:53:23 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 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, MeSH
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 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 DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point68 - 69 °CNot Available
Boiling Point156.00 to 157.00 °C. @ 3.50 mm HgThe Good Scents Company Information System
Water Solubility0.21 mg/mL at 20 °CNot Available
LogP3.57Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+145.44831661259
DarkChem[M-H]-140.49631661259
DeepCCS[M+H]+147.88330932474
DeepCCS[M-H]-144.05430932474
DeepCCS[M-2H]-181.38630932474
DeepCCS[M+Na]+156.92530932474
AllCCS[M+H]+144.032859911
AllCCS[M+H-H2O]+140.032859911
AllCCS[M+NH4]+147.732859911
AllCCS[M+Na]+148.832859911
AllCCS[M-H]-146.632859911
AllCCS[M+Na-2H]-147.432859911
AllCCS[M+HCOO]-148.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ButylparabenCCCCOC(=O)C1=CC=C(O)C=C12422.5Standard polar33892256
ButylparabenCCCCOC(=O)C1=CC=C(O)C=C11677.9Standard non polar33892256
ButylparabenCCCCOC(=O)C1=CC=C(O)C=C11743.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Butylparaben,1TMS,isomer #1CCCCOC(=O)C1=CC=C(O[Si](C)(C)C)C=C11780.1Semi standard non polar33892256
Butylparaben,1TBDMS,isomer #1CCCCOC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12004.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Butylparaben EI-B (Non-derivatized)splash10-00dr-2900000000-bb56a149a6da74d93ee82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Butylparaben EI-B (Non-derivatized)splash10-0079-3900000000-3c58d2a06f7053d6232c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Butylparaben EI-B (Non-derivatized)splash10-00dr-2900000000-bb56a149a6da74d93ee82018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Butylparaben EI-B (Non-derivatized)splash10-0079-3900000000-3c58d2a06f7053d6232c2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Butylparaben GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-5900000000-a07eb5ffe2dd5224cc422017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Butylparaben GC-MS (1 TMS) - 70eV, Positivesplash10-0006-4900000000-b50d93adc6a9e391c4672017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Butylparaben GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00dr-3900000000-0366956a08d3509a13f72014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Butylparaben LC-ESI-ITFT , negative-QTOFsplash10-0006-0900000000-e5adfc9cf6eccf247f8a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Butylparaben LC-ESI-ITFT , negative-QTOFsplash10-0006-0900000000-2b574dc259808331afc72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Butylparaben LC-ESI-ITFT , negative-QTOFsplash10-000i-1900000000-831ef1d350d13780a3292017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Butylparaben LC-ESI-ITFT , negative-QTOFsplash10-000i-1900000000-ce6d6917117d7a334d952017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Butylparaben LC-ESI-QFT , negative-QTOFsplash10-0006-0900000000-56813e9a5bacca3c57f92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Butylparaben LC-ESI-ITFT , negative-QTOFsplash10-0006-0900000000-e5adfc9cf6eccf247f8a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Butylparaben LC-ESI-ITFT , negative-QTOFsplash10-0006-0900000000-2b574dc259808331afc72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Butylparaben LC-ESI-ITFT , negative-QTOFsplash10-000i-1900000000-831ef1d350d13780a3292017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Butylparaben LC-ESI-ITFT , negative-QTOFsplash10-000i-1900000000-ce6d6917117d7a334d952017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Butylparaben LC-ESI-ITFT , positive-QTOFsplash10-0072-9800000000-fe4706758a9d399987b92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Butylparaben LC-ESI-ITFT , positive-QTOFsplash10-001i-9500000000-8c7830a4583c649d27532017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Butylparaben LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-4981588a915a613086d02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Butylparaben LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-a1bc78b908d3b7a1fb172017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Butylparaben LC-ESI-ITFT , positive-QTOFsplash10-0072-9800000000-fe4706758a9d399987b92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Butylparaben LC-ESI-ITFT , positive-QTOFsplash10-001i-9500000000-8c7830a4583c649d27532017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Butylparaben LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-4981588a915a613086d02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Butylparaben LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-a1bc78b908d3b7a1fb172017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Butylparaben 30V, Positive-QTOFsplash10-00dr-0900000000-ec37bfdb07ea8c0fc84a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Butylparaben 40V, Positive-QTOFsplash10-00di-0900000000-163529e9ff8dd2665de22021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butylparaben 10V, Positive-QTOFsplash10-0002-2900000000-5c2e16e5df0c1640445a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butylparaben 20V, Positive-QTOFsplash10-0ab9-9600000000-d8a6a3f37504b01c37732015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butylparaben 40V, Positive-QTOFsplash10-0abc-9200000000-df6492b55ad6172bd44f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butylparaben 10V, Negative-QTOFsplash10-0006-1900000000-aec24ddd4de8f43b0a062015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butylparaben 20V, Negative-QTOFsplash10-000f-3900000000-ef4eb95372bf56bcd2942015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butylparaben 40V, Negative-QTOFsplash10-00kf-9400000000-34d1624c244b2672ad382015-04-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
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
MarkerDB IDNot Available
Good Scents IDrw1007641
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.. .