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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:18:17 UTC
Update Date2021-10-13 06:41:33 UTC
HMDB IDHMDB0034462
Secondary Accession Numbers
  • HMDB34462
Metabolite Identification
Common NameHeptyl 4-hydroxybenzoate
DescriptionHeptyl 4-hydroxybenzoate, also known as heptylparaben or nipaheptyl, 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. Heptyl 4-hydroxybenzoate is used as a food additive ("EAFUS: Everything Added to Food in the United States. "). Heptyl 4-hydroxybenzoate is a potentially toxic compound. No indication of carcinogenicity to humans (not listed by IARC). These are compounds containing an hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxylic acid. It is used as a food additive .
Structure
Data?1563862567
Synonyms
ValueSource
HeptylparabenKegg
Heptyl 4-hydroxybenzoic acidGenerator
Benzoic acid, 4-hydroxy-, heptyl esterHMDB
Benzoic acid, 4-hydroxy-, N-heptyl esterHMDB
Benzoic acid, P-hydroxy-, heptyl esterHMDB
Heptyl P-hydroxy benzoateHMDB
Heptyl P-hydroxybenzoateHMDB
Heptyl parabenHMDB
N-Heptyl 4-hydroxybenzoateHMDB
N-Heptyl P-hydroxybenzoateHMDB
NipaheptylHMDB
P-Hydroxybenzoic acid heptyl esterHMDB
staypro WS 7HMDB
Heptyl p-hydroxybenzoic acidGenerator
Chemical FormulaC14H20O3
Average Molecular Weight236.3068
Monoisotopic Molecular Weight236.141244506
IUPAC Nameheptyl 4-hydroxybenzoate
Traditional Nameheptylparaben
CAS Registry Number1085-12-7
SMILES
CCCCCCCOC(=O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C14H20O3/c1-2-3-4-5-6-11-17-14(16)12-7-9-13(15)10-8-12/h7-10,15H,2-6,11H2,1H3
InChI KeyZTJORNVITHUQJA-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
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point49 - 51 °CNot Available
Boiling Point353.63 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.02 mg/mL at 30 °CNot Available
LogP4.83Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.035 g/LALOGPS
logP10(4.96) g/LALOGPS
logP10(4.33) g/LChemAxon
logS10(-3.8) g/LALOGPS
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 Count8ChemAxon
Refractivity67.74 m³·mol⁻¹ChemAxon
Polarizability27.81 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]+157.40831661259
DarkChem[M-H]-156.45331661259
DeepCCS[M+H]+161.93730932474
DeepCCS[M-H]-158.81730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Heptyl 4-hydroxybenzoateCCCCCCCOC(=O)C1=CC=C(O)C=C12850.0Standard polar33892256
Heptyl 4-hydroxybenzoateCCCCCCCOC(=O)C1=CC=C(O)C=C11951.7Standard non polar33892256
Heptyl 4-hydroxybenzoateCCCCCCCOC(=O)C1=CC=C(O)C=C12076.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Heptyl 4-hydroxybenzoate,1TMS,isomer #1CCCCCCCOC(=O)C1=CC=C(O[Si](C)(C)C)C=C12082.7Semi standard non polar33892256
Heptyl 4-hydroxybenzoate,1TBDMS,isomer #1CCCCCCCOC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12292.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Heptyl 4-hydroxybenzoate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-6900000000-d6701309efb7422d3d182017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heptyl 4-hydroxybenzoate GC-MS (1 TMS) - 70eV, Positivesplash10-0006-6900000000-f1d3af9e0c68bafdb44f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heptyl 4-hydroxybenzoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0079-5900000000-3d83e4cf98254eb3e0622014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 90V, Negative-QTOFsplash10-0006-9300000000-04df92f5b7ea8aee4cc22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 75V, Negative-QTOFsplash10-0006-9300000000-462e81e1a1b1d6e119152021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 15V, Negative-QTOFsplash10-000i-0090000000-a25d515550160be98efe2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 30V, Negative-QTOFsplash10-000i-1390000000-02444847a35bf78a72ad2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 60V, Negative-QTOFsplash10-0006-9500000000-eef56f5be2f6dffba5b62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 45V, Negative-QTOFsplash10-000i-6920000000-4d0caf07016ac7adc2812021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 10V, Positive-QTOFsplash10-000i-3390000000-9d5d7a09a34e5154f0372016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 20V, Positive-QTOFsplash10-006t-9410000000-630af20fa929cdb0263f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 40V, Positive-QTOFsplash10-006x-9200000000-a3b5b661554d8ef165c72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 10V, Negative-QTOFsplash10-000i-2390000000-cb5171ec4305db7885a12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 20V, Negative-QTOFsplash10-000i-4920000000-ee414667448b4c454b782016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 40V, Negative-QTOFsplash10-00ko-9400000000-7b1ffd799d20e79a40772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 10V, Positive-QTOFsplash10-000i-2690000000-1b18cc5b280969e4eaa52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 20V, Positive-QTOFsplash10-00di-5900000000-7e746c44ef2dfcda9e492021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 40V, Positive-QTOFsplash10-00di-9600000000-149b8353bc9688d4bdbf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 10V, Negative-QTOFsplash10-000i-0190000000-78db36f57f97d1bbfa732021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 20V, Negative-QTOFsplash10-0006-9300000000-9cd7041d6f91d1409a332021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 40V, Negative-QTOFsplash10-0006-9100000000-1bc7095d8bbc3de55a802021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012871
KNApSAcK IDNot Available
Chemspider ID13515
KEGG Compound IDC14718
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14138
PDB IDNot Available
ChEBI ID17879
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1438321
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .