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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-05-18 14:35:46 UTC

Update Date

2020-02-26 21:39:04 UTC

HMDB ID

HMDB0013733

Secondary Accession Numbers

HMDB13733

Metabolite Identification

Common Name

1,2,4-Trimethylbenzene

Description

1,2,4-Trimethylbenzene, also known as pseudocumene or psi-cumene, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. 1,2,4-Trimethylbenzene exists in all eukaryotes, ranging from yeast to plants to humans. 1,2,4-Trimethylbenzene is a plastic tasting compound. 1,2,4-Trimethylbenzene is found, on average, in the highest concentration within black walnuts (Juglans nigra). 1,2,4-Trimethylbenzene has also been detected, but not quantified in, a few different foods, such as cauliflowers (Brassica oleracea var. botrytis), corns (Zea mays), and sweet cherries (Prunus avium). This could make 1,2,4-trimethylbenzene a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on 1,2,4-Trimethylbenzene.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,3,4-Trimethylbenzene	ChEBI
As-trimethylbenzene	ChEBI
Pseudocumene	ChEBI
Pseudocumol	ChEBI
Psi-cumene	ChEBI
Uns-trimethylbenzene	ChEBI
.psi.-cumene	HMDB
1,2, 4-Trimethylbenzene	HMDB
1,2,4-Trimethyl-benzene	HMDB
1,2,4-Trimethylbenzene (acd/name 4.0)	HMDB
1,2,4-Trimethylbenzene (pseudocumene)	HMDB
1,2,5-Trimethyl-benzene	HMDB
1,2,5-Trimethylbenzene	HMDB
Asymmetrical trimethylbenzene	HMDB
Laquo psiraquo -cumene	HMDB

Chemical Formula

C₉H₁₂

Average Molecular Weight

120.1916

Monoisotopic Molecular Weight

120.093900384

IUPAC Name

1,2,4-trimethylbenzene

Traditional Name

1,2,4-trimethylbenzene

CAS Registry Number

95-63-6

SMILES

CC1=CC(C)=C(C)C=C1

InChI Identifier

InChI=1S/C9H12/c1-7-4-5-8(2)9(3)6-7/h4-6H,1-3H3

InChI Key

GWHJZXXIDMPWGX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Aromatic hydrocarbon
Unsaturated hydrocarbon
Hydrocarbon
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

trimethylbenzene (CHEBI:34039 )
a small molecule (PSEUDOCUMENE )

Ontology

Not Available

Exogenous (HMDB: HMDB0013733)

Food

Nut

Black walnut (FooDB: FOOD00093)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-43.8 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.057 mg/mL at 25 °C	Not Available
LogP	3.63	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.082 g/L	ALOGPS
logP	3.62	ALOGPS
logP	3.51	ChemAxon
logS	-3.2	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	41.18 m³·mol⁻¹	ChemAxon
Polarizability	15.12 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	126.348	31661259
DarkChem	[M-H]-	123.599	31661259
DeepCCS	[M+H]+	133.031	30932474
DeepCCS	[M-H]-	129.203	30932474
DeepCCS	[M-2H]-	166.656	30932474
DeepCCS	[M+Na]+	142.195	30932474
AllCCS	[M+H]+	118.4	32859911
AllCCS	[M+H-H2O]+	113.4	32859911
AllCCS	[M+NH4]+	123.0	32859911
AllCCS	[M+Na]+	124.3	32859911
AllCCS	[M-H]-	120.6	32859911
AllCCS	[M+Na-2H]-	122.6	32859911
AllCCS	[M+HCOO]-	124.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	6.0 minutes	32390414
Predicted by Siyang on May 30, 2022	17.1076 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.97 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1870.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	634.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	247.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	438.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	334.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	731.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	729.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	237.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1472.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	589.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1609.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	506.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	447.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	541.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	394.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	35.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,2,4-Trimethylbenzene	CC1=CC(C)=C(C)C=C1	1293.0	Standard polar	33892256
1,2,4-Trimethylbenzene	CC1=CC(C)=C(C)C=C1	977.0	Standard non polar	33892256
1,2,4-Trimethylbenzene	CC1=CC(C)=C(C)C=C1	996.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 1,2,4-Trimethylbenzene EI-B (Non-derivatized)	splash10-0ab9-4900000000-cd43d59aff7151b5c417	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2,4-Trimethylbenzene EI-B (Non-derivatized)	splash10-0ab9-0900000000-f6eddce0977d81a0a39c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2,4-Trimethylbenzene CI-B (Non-derivatized)	splash10-00di-0900000000-ce7d4aadbd433a795e8c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2,4-Trimethylbenzene CI-B (Non-derivatized)	splash10-00di-0900000000-95755809a6a91918193b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2,4-Trimethylbenzene EI-B (Non-derivatized)	splash10-0ab9-4900000000-cd43d59aff7151b5c417	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2,4-Trimethylbenzene EI-B (Non-derivatized)	splash10-0ab9-0900000000-f6eddce0977d81a0a39c	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2,4-Trimethylbenzene CI-B (Non-derivatized)	splash10-00di-0900000000-ce7d4aadbd433a795e8c	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2,4-Trimethylbenzene CI-B (Non-derivatized)	splash10-00di-0900000000-95755809a6a91918193b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,4-Trimethylbenzene GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-5900000000-961ef37bde9c772ea487	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,4-Trimethylbenzene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,4-Trimethylbenzene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-6900000000-bce340b6ca401894e681	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4-Trimethylbenzene 10V, Positive-QTOF	splash10-00di-0900000000-4722929cddd1686976eb	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4-Trimethylbenzene 20V, Positive-QTOF	splash10-00di-1900000000-3a43e490603114eefd1b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4-Trimethylbenzene 40V, Positive-QTOF	splash10-0zi0-9300000000-8c265f9f11b5b4d61a91	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4-Trimethylbenzene 10V, Negative-QTOF	splash10-014i-0900000000-5c09d4acb0c77b581c17	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4-Trimethylbenzene 20V, Negative-QTOF	splash10-014i-0900000000-053f4378eb6b7013236a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4-Trimethylbenzene 40V, Negative-QTOF	splash10-0gb9-5900000000-e3c7b25395d693c9f32c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4-Trimethylbenzene 10V, Positive-QTOF	splash10-00di-3900000000-b11604b10012c55d83bf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4-Trimethylbenzene 20V, Positive-QTOF	splash10-05dl-9500000000-0b256c3eb12a7fce9903	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4-Trimethylbenzene 40V, Positive-QTOF	splash10-004i-9200000000-00c61a9869c0cd707236	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4-Trimethylbenzene 10V, Negative-QTOF	splash10-014i-0900000000-794ffb5dd5f7d8f3ef50	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4-Trimethylbenzene 20V, Negative-QTOF	splash10-014i-0900000000-dc6442d855de952333c1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4-Trimethylbenzene 40V, Negative-QTOF	splash10-014i-9200000000-ca5f06b0a9b4786d4361	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22284503	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Breast cancer	22284503	details

Associated Disorders and Diseases

Disease References

Perillyl alcohol administration for cancer treatment
Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005815

KNApSAcK ID

Not Available

Chemspider ID

6977

KEGG Compound ID

C14533

BioCyc ID

PSEUDOCUMENE

BiGG ID

Not Available

Wikipedia Link

1,2,4-Trimethylbenzene

METLIN ID

Not Available

PubChem Compound

7247

PDB ID

Not Available

ChEBI ID

34039

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 1,2,4-Trimethylbenzene (HMDB0013733)

MOL for HMDB0013733 (1,2,4-Trimethylbenzene)

3D MOL for HMDB0013733 (1,2,4-Trimethylbenzene)

3D SDF for HMDB0013733 (1,2,4-Trimethylbenzene)

3D-SDF for HMDB0013733 (1,2,4-Trimethylbenzene)

PDB for HMDB0013733 (1,2,4-Trimethylbenzene)

3D PDB for HMDB0013733 (1,2,4-Trimethylbenzene)

SMILES for HMDB0013733 (1,2,4-Trimethylbenzene)

INCHI for HMDB0013733 (1,2,4-Trimethylbenzene)

Structure for HMDB0013733 (1,2,4-Trimethylbenzene)

3D Structure for HMDB0013733 (1,2,4-Trimethylbenzene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra