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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:47:14 UTC

Update Date

2023-02-21 17:21:28 UTC

HMDB ID

HMDB0032016

Secondary Accession Numbers

HMDB32016

Metabolite Identification

Common Name

2,4,6-Trimethylbenzaldehyde

Description

2,4,6-Trimethylbenzaldehyde, also known as 2-mesitylenecarboxaldehyde or b-isodural, belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-). Based on a literature review a significant number of articles have been published on 2,4,6-Trimethylbenzaldehyde.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,4,6-Trimethyl-benzaldehyde	HMDB
2-Formyl-1,3,5-trimethylbenzene	HMDB
2-Formylmesitylene	HMDB
2-Mesitylenecarboxaldehyde	HMDB
Aldehydomesitylene	HMDB
b-Isodural	HMDB
b-Isoduryl aldehyde	HMDB
Isodural	HMDB
Mesitaldehyde	HMDB
Mesityl aldehyde	HMDB
Mesitylaldehyde	HMDB
Mesitylenecarboxaldehyde	HMDB

Chemical Formula

C₁₀H₁₂O

Average Molecular Weight

148.2017

Monoisotopic Molecular Weight

148.088815006

IUPAC Name

2,4,6-trimethylbenzaldehyde

Traditional Name

benzaldehyde, 2,4,6-trimethyl-

CAS Registry Number

487-68-3

SMILES

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

InChI Identifier

InChI=1S/C10H12O/c1-7-4-8(2)10(6-11)9(3)5-7/h4-6H,1-3H3

InChI Key

HIKRJHFHGKZKRI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-).

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoyl derivatives

Direct Parent

Benzoyl derivatives

Alternative Parents

Substituents

Benzoyl
Benzaldehyde
Aryl-aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aldehyde
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0032016)
Cell membrane (HMDB: HMDB0032016)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032016)

Source

Endogenous

Endogenous (HMDB: HMDB0032016)

Plant

Plant (HMDB: HMDB0032016)

Exogenous

Food

Food (HMDB: HMDB0032016)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0032016)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	14 °C	Not Available
Boiling Point	238.50 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	106 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.020 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.13 g/L	ALOGPS
logP	2.59	ALOGPS
logP	3.23	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	47.77 m³·mol⁻¹	ChemAxon
Polarizability	17.22 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]+	131.295	31661259
DarkChem	[M-H]-	129.709	31661259
DeepCCS	[M+H]+	138.674	30932474
DeepCCS	[M-H]-	134.933	30932474
DeepCCS	[M-2H]-	172.71	30932474
DeepCCS	[M+Na]+	148.249	30932474
AllCCS	[M+H]+	127.9	32859911
AllCCS	[M+H-H2O]+	123.3	32859911
AllCCS	[M+NH4]+	132.2	32859911
AllCCS	[M+Na]+	133.4	32859911
AllCCS	[M-H]-	129.6	32859911
AllCCS	[M+Na-2H]-	130.9	32859911
AllCCS	[M+HCOO]-	132.4	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.	6.18 minutes	32390414
Predicted by Siyang on May 30, 2022	16.2865 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.95 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1701.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	578.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	214.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	386.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	207.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	678.1 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	755.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	137.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1391.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	509.8 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	1509.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	444.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	433.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	502.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	420.5 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	39.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,4,6-Trimethylbenzaldehyde	CC1=CC(C)=C(C=O)C(C)=C1	1891.9	Standard polar	33892256
2,4,6-Trimethylbenzaldehyde	CC1=CC(C)=C(C=O)C(C)=C1	1274.1	Standard non polar	33892256
2,4,6-Trimethylbenzaldehyde	CC1=CC(C)=C(C=O)C(C)=C1	1351.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2,4,6-Trimethylbenzaldehyde EI-B (Non-derivatized)	splash10-0002-5900000000-65fb57ab90261d73ba23	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,4,6-Trimethylbenzaldehyde EI-B (Non-derivatized)	splash10-0002-5900000000-65fb57ab90261d73ba23	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4,6-Trimethylbenzaldehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-1900000000-6c428decf4c845ad6edd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4,6-Trimethylbenzaldehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,6-Trimethylbenzaldehyde 10V, Positive-QTOF	splash10-0002-0900000000-60d5293effe1928c3a07	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,6-Trimethylbenzaldehyde 20V, Positive-QTOF	splash10-0002-0900000000-887982e0ceca59294689	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,6-Trimethylbenzaldehyde 40V, Positive-QTOF	splash10-067l-9600000000-dd84795abe2f8b8de7af	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,6-Trimethylbenzaldehyde 10V, Negative-QTOF	splash10-0002-0900000000-fdac2140c7f2331fcd34	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,6-Trimethylbenzaldehyde 20V, Negative-QTOF	splash10-0002-0900000000-762f7d3c0b1eb62d4d0e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,6-Trimethylbenzaldehyde 40V, Negative-QTOF	splash10-000t-3900000000-df0cd3eef9e6dce7eebd	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,6-Trimethylbenzaldehyde 10V, Negative-QTOF	splash10-014i-0900000000-794ffb5dd5f7d8f3ef50	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,6-Trimethylbenzaldehyde 20V, Negative-QTOF	splash10-014i-0900000000-794ffb5dd5f7d8f3ef50	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,6-Trimethylbenzaldehyde 40V, Negative-QTOF	splash10-014i-0900000000-794ffb5dd5f7d8f3ef50	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,6-Trimethylbenzaldehyde 10V, Positive-QTOF	splash10-00r2-0900000000-ad4e4dbcd6bef9b919c4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,6-Trimethylbenzaldehyde 20V, Positive-QTOF	splash10-066r-1900000000-1d8e070d975721ec7568	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,6-Trimethylbenzaldehyde 40V, Positive-QTOF	splash10-066r-9800000000-e9686241b1c944d621cb	2021-09-22	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008714

KNApSAcK ID

C00053963

Chemspider ID

21168786

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10254

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1257151

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2,4,6-Trimethylbenzaldehyde (HMDB0032016)

MOL for HMDB0032016 (2,4,6-Trimethylbenzaldehyde)

3D MOL for HMDB0032016 (2,4,6-Trimethylbenzaldehyde)

3D SDF for HMDB0032016 (2,4,6-Trimethylbenzaldehyde)

3D-SDF for HMDB0032016 (2,4,6-Trimethylbenzaldehyde)

PDB for HMDB0032016 (2,4,6-Trimethylbenzaldehyde)

3D PDB for HMDB0032016 (2,4,6-Trimethylbenzaldehyde)

SMILES for HMDB0032016 (2,4,6-Trimethylbenzaldehyde)

INCHI for HMDB0032016 (2,4,6-Trimethylbenzaldehyde)

Structure for HMDB0032016 (2,4,6-Trimethylbenzaldehyde)

3D Structure for HMDB0032016 (2,4,6-Trimethylbenzaldehyde)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra