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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:31:44 UTC
Update Date2022-03-07 02:52:14 UTC
HMDB IDHMDB0029641
Secondary Accession Numbers
  • HMDB29641
Metabolite Identification
Common Namep-Mentha-1,3,5,8-tetraene
Descriptionp-Mentha-1,3,5,8-tetraene, also known as 4-isopropenyltoluene, belongs to the class of organic compounds known as phenylpropenes. Phenylpropenes are compounds containing a phenylpropene moiety, which consists of a propene substituent bound to a phenyl group. p-Mentha-1,3,5,8-tetraene is a citrus, clove, and gasoline tasting compound. p-Mentha-1,3,5,8-tetraene is found, on average, in the highest concentration within red wine and star anises (Illicium verum). p-Mentha-1,3,5,8-tetraene has also been detected, but not quantified in, several different foods, such as lemons (Citrus limon), spearmints (Mentha spicata), parsleys (Petroselinum crispum), evergreen blackberries (Rubus laciniatus), and dills (Anethum graveolens). This could make p-mentha-1,3,5,8-tetraene a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on p-Mentha-1,3,5,8-tetraene.
Structure
Data?1582753445
Synonyms
ValueSource
4-IsopropenyltolueneMeSH
1-Isopropenyl-4-methylbenzeneHMDB
1-Methyl-4-(1-methylethenyl)-benzeneHMDB
1-Methyl-4-(1-methylethenyl)benzeneHMDB
1-Methyl-4-(1-methylethenyl)benzene, 9ciHMDB
1-Methyl-4-isopropenylbenzeneHMDB
1-Methyl-4alpha-methylstyreneHMDB
2-(4-Methylphenyl)propeneHMDB
2-(P-Methylphenyl)propeneHMDB
2-P-TolylpropeneHMDB
4-Methyl-alpha-methylstyreneHMDB
4-MethylisopropenylbenzeneHMDB
alpha,4-DimethylstyreneHMDB
alpha,P-DimethylstyreneHMDB
alpha-Dimethyl-P-styreneHMDB
alpha-Methyl-P-methylstyreneHMDB
alpha-P DimethylstyreneHMDB
CymeneneHMDB
dehydro-P-CymeneHMDB
FEMA 3144HMDB
Ghl.PD_Mitscher_leg0.317HMDB
Isopropenyl toluene cHMDB
Methyl-4-(1-methylethenyl)-benzeneHMDB
Methyl-P-isopropenylbenzeneHMDB
P,a-Dimethylstyrene, 8ciHMDB
P,alpha-Dimethyl-styreneHMDB
P,alpha-DimethylstyreneHMDB
P,alpha-DimethylstyrolHMDB
P-alpha-Dimethyl-styreneHMDB
P-alpha-DimethylstyreneHMDB
P-CymeneneHMDB
P-Isopropenyl tolueneHMDB
P-IsopropenyltolueneHMDB
P-Methyl-alpha-methylstyreneHMDB
Para- alpha-dimethylstyreneHMDB
Chemical FormulaC10H12
Average Molecular Weight132.2023
Monoisotopic Molecular Weight132.093900384
IUPAC Name1-methyl-4-(prop-1-en-2-yl)benzene
Traditional Name1-methyl-4-(prop-1-en-2-yl)benzene
CAS Registry Number1195-32-0
SMILES
CC(=C)C1=CC=C(C)C=C1
InChI Identifier
InChI=1S/C10H12/c1-8(2)10-6-4-9(3)5-7-10/h4-7H,1H2,2-3H3
InChI KeyMMSLOZQEMPDGPI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropenes. Phenylpropenes are compounds containing a phenylpropene moiety, which consists of a propene substituent bound to a phenyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropenes
Direct ParentPhenylpropenes
Alternative Parents
Substituents
  • Phenylpropene
  • Styrene
  • Toluene
  • Aromatic hydrocarbon
  • Branched unsaturated hydrocarbon
  • Cyclic olefin
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-20 °CNot Available
Boiling Point186.00 to 189.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility35.29 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.782 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP3.79ALOGPS
logP3.52ChemAxon
logS-2.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity45.07 m³·mol⁻¹ChemAxon
Polarizability16.35 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+130.51131661259
DarkChem[M-H]-128.92531661259
DeepCCS[M+H]+134.73830932474
DeepCCS[M-H]-131.49130932474
DeepCCS[M-2H]-168.58730932474
DeepCCS[M+Na]+144.12530932474
AllCCS[M+H]+122.232859911
AllCCS[M+H-H2O]+117.432859911
AllCCS[M+NH4]+126.732859911
AllCCS[M+Na]+128.032859911
AllCCS[M-H]-124.232859911
AllCCS[M+Na-2H]-125.732859911
AllCCS[M+HCOO]-127.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
p-Mentha-1,3,5,8-tetraeneCC(=C)C1=CC=C(C)C=C11434.5Standard polar33892256
p-Mentha-1,3,5,8-tetraeneCC(=C)C1=CC=C(C)C=C11048.5Standard non polar33892256
p-Mentha-1,3,5,8-tetraeneCC(=C)C1=CC=C(C)C=C11085.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - p-Mentha-1,3,5,8-tetraene GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-5900000000-42122b872bf255e286672016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Mentha-1,3,5,8-tetraene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-014i-7900000000-8a35d379c53b742012db2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Mentha-1,3,5,8-tetraene 10V, Positive-QTOFsplash10-001i-0900000000-1a859e9677580ea17b572016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Mentha-1,3,5,8-tetraene 20V, Positive-QTOFsplash10-001i-1900000000-2fd4472dcad1e8a7e9492016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Mentha-1,3,5,8-tetraene 40V, Positive-QTOFsplash10-0159-7900000000-c9e2399b68bfd80c5f892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Mentha-1,3,5,8-tetraene 10V, Negative-QTOFsplash10-001i-0900000000-564cd5c06312dcea67ff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Mentha-1,3,5,8-tetraene 20V, Negative-QTOFsplash10-001i-0900000000-abfffa532b094cd938692016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Mentha-1,3,5,8-tetraene 40V, Negative-QTOFsplash10-0159-3900000000-f77c6849e823907a8ecf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Mentha-1,3,5,8-tetraene 10V, Negative-QTOFsplash10-001i-0900000000-b6dbb79105fa765a1a392021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Mentha-1,3,5,8-tetraene 20V, Negative-QTOFsplash10-001i-0900000000-e787ac89e5bc523fe9202021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Mentha-1,3,5,8-tetraene 40V, Negative-QTOFsplash10-014i-4900000000-f20794dba4e302324ade2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Mentha-1,3,5,8-tetraene 10V, Positive-QTOFsplash10-001i-1900000000-7a77bd4827fc7193683c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Mentha-1,3,5,8-tetraene 20V, Positive-QTOFsplash10-0006-9300000000-8f432d1b83b7ee6d6dc82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Mentha-1,3,5,8-tetraene 40V, Positive-QTOFsplash10-004i-9000000000-b7bc284e37a86692377c2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn's disease
details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Crohn's disease
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000812
KNApSAcK IDC00010905
Chemspider ID56173
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound62385
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1018551
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.. .