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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:31:47 UTC

Update Date

2023-02-21 17:18:56 UTC

HMDB ID

HMDB0029648

Secondary Accession Numbers

HMDB29648

Metabolite Identification

Common Name

2,4,5-Trimethoxybenzaldehyde

Description

2,4,5-Trimethoxybenzaldehyde, also known as TMBZ or asaraldehyde, 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-). 2,4,5-Trimethoxybenzaldehyde has been detected, but not quantified, in several different foods, such as carrots, herbs and spices, root vegetables, and wild carrots. This could make 2,4,5-trimethoxybenzaldehyde a potential biomarker for the consumption of these foods.

Structure

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

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0       3.387  -0.769   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.001  -1.539   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.615  -0.769   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.769  -1.539   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.001  -0.769   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.387  -1.539   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.387  -3.079   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.233   2.463   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.001   1.693   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.615   0.769   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.769   1.539   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.001   0.769   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.387   1.539   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.387   3.079   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    9                                                            
CONECT    9    8   10                                                       
CONECT   10    3    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12    5   11   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0029648
HETATM    1  C1  UNL     1       2.992  -1.981  -0.055  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.682  -0.598  -0.067  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.389  -0.122  -0.038  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.350  -1.026   0.006  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.933  -0.531   0.035  1.00  0.00           C  
HETATM    6  O2  UNL     1      -2.012  -1.382   0.080  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.944  -2.770   0.099  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.169   0.840   0.021  1.00  0.00           C  
HETATM    9  O3  UNL     1      -2.475   1.306   0.051  1.00  0.00           O  
HETATM   10  C7  UNL     1      -2.730   2.688   0.037  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.109   1.740  -0.023  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.176   1.244  -0.053  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.293   2.158  -0.099  1.00  0.00           C  
HETATM   14  O4  UNL     1       2.095   3.388  -0.112  1.00  0.00           O  
HETATM   15  H1  UNL     1       2.733  -2.368   0.943  1.00  0.00           H  
HETATM   16  H2  UNL     1       4.053  -2.178  -0.247  1.00  0.00           H  
HETATM   17  H3  UNL     1       2.360  -2.546  -0.798  1.00  0.00           H  
HETATM   18  H4  UNL     1       0.549  -2.086   0.017  1.00  0.00           H  
HETATM   19  H5  UNL     1      -2.864  -3.155  -0.428  1.00  0.00           H  
HETATM   20  H6  UNL     1      -1.092  -3.208  -0.441  1.00  0.00           H  
HETATM   21  H7  UNL     1      -1.999  -3.213   1.117  1.00  0.00           H  
HETATM   22  H8  UNL     1      -2.213   3.130  -0.843  1.00  0.00           H  
HETATM   23  H9  UNL     1      -2.307   3.202   0.930  1.00  0.00           H  
HETATM   24  H10 UNL     1      -3.810   2.876  -0.088  1.00  0.00           H  
HETATM   25  H11 UNL     1      -0.313   2.809  -0.034  1.00  0.00           H  
HETATM   26  H12 UNL     1       3.298   1.784  -0.122  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3
CONECT    3    4    4   12
CONECT    4    5   18
CONECT    5    6    8    8
CONECT    6    7
CONECT    7   19   20   21
CONECT    8    9   11
CONECT    9   10
CONECT   10   22   23   24
CONECT   11   12   12   25
CONECT   12   13
CONECT   13   14   14   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
TMBZ	MeSH
2,4,5-Trimethoxy benzaldehyde	HMDB
2,4,5-Trimethoxy-benzaldehyd	HMDB
2,4,5-Trimethoxy-benzaldehyde	HMDB
2,4,5-Trimethoxybenzaldehyde, 9ci, 8ci	HMDB
2,4,5-Trimethoxybenzaldheyde	HMDB
3,4, 6-Trimethoxybenzaldehyde	HMDB
3,4,6-Trimethoxybenzaldehyde	HMDB
Asaraldehyde	HMDB
Asaronaldehyde	HMDB
Asarylaldehyde	HMDB
Azarylaldehyde	HMDB
Gazarin	HMDB

Chemical Formula

C₁₀H₁₂O₄

Average Molecular Weight

196.1999

Monoisotopic Molecular Weight

196.073558872

IUPAC Name

2,4,5-trimethoxybenzaldehyde

Traditional Name

2,4,5-trimethoxybenzaldehyde

CAS Registry Number

4460-86-0

SMILES

COC1=CC(OC)=C(OC)C=C1C=O

InChI Identifier

InChI=1S/C10H12O4/c1-12-8-5-10(14-3)9(13-2)4-7(8)6-11/h4-6H,1-3H3

InChI Key

IAJBQAYHSQIQRE-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

Phenoxy compound
Methoxybenzene
Phenol ether
Benzoyl
Benzaldehyde
Anisole
Aryl-aldehyde
Alkyl aryl ether
Ether
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

Extracellular (HMDB: HMDB0029648)
Cytoplasm (HMDB: HMDB0029648)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029648)

Source

Endogenous

Endogenous (HMDB: HMDB0029648)

Plant

Plant (HMDB: HMDB0029648)

Exogenous

Food

Food (HMDB: HMDB0029648)

Vegetable

Root vegetable

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	114 °C	Not Available
Boiling Point	334.00 to 335.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	2716 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.634 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	138.32	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000902

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.11 g/L	ALOGPS
logP	1.46	ALOGPS
logP	1.21	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	52.03 m³·mol⁻¹	ChemAxon
Polarizability	19.78 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	145.45	31661259
DarkChem	[M-H]-	145.562	31661259
DeepCCS	[M+H]+	143.198	30932474
DeepCCS	[M-H]-	140.766	30932474
DeepCCS	[M-2H]-	176.373	30932474
DeepCCS	[M+Na]+	151.8	30932474
AllCCS	[M+H]+	143.0	32859911
AllCCS	[M+H-H2O]+	138.8	32859911
AllCCS	[M+NH4]+	146.8	32859911
AllCCS	[M+Na]+	147.9	32859911
AllCCS	[M-H]-	142.6	32859911
AllCCS	[M+Na-2H]-	143.4	32859911
AllCCS	[M+HCOO]-	144.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,4,5-Trimethoxybenzaldehyde	COC1=CC(OC)=C(OC)C=C1C=O	2616.7	Standard polar	33892256
2,4,5-Trimethoxybenzaldehyde	COC1=CC(OC)=C(OC)C=C1C=O	1572.9	Standard non polar	33892256
2,4,5-Trimethoxybenzaldehyde	COC1=CC(OC)=C(OC)C=C1C=O	1739.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4,5-Trimethoxybenzaldehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gc0-2900000000-35233ece3a62ad8a35d2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4,5-Trimethoxybenzaldehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-4900000000-662e5b21287ffac89246	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,4,5-Trimethoxybenzaldehyde DI-ESI-qTof , Positive-QTOF	splash10-00kr-0900000000-d9d3fcc4abd8923984cc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,4,5-Trimethoxybenzaldehyde LC-ESI-qTof , Positive-QTOF	splash10-00dr-1900000000-07ddc3ea392f7b2e02dd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,4,5-Trimethoxybenzaldehyde Linear Ion Trap , positive-QTOF	splash10-0v4i-0890000000-3de28a9b3adce65468e2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,4,5-Trimethoxybenzaldehyde , positive-QTOF	splash10-00dr-1900000000-07ddc3ea392f7b2e02dd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,4,5-Trimethoxybenzaldehyde 40V, Positive-QTOF	splash10-00di-0900000000-ce5c946a2462816dd664	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,4,5-Trimethoxybenzaldehyde 15V, Positive-QTOF	splash10-00kb-0900000000-5962b70336db75978f97	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,4,5-Trimethoxybenzaldehyde 20V, Positive-QTOF	splash10-000i-0900000000-668562cd98ced84d6e4f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,4,5-Trimethoxybenzaldehyde 10V, Positive-QTOF	splash10-00kb-0900000000-d0986132cdcbfb538340	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,4,5-Trimethoxybenzaldehyde 30V, Positive-QTOF	splash10-014j-0900000000-795e38bb9393439ac060	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,4,5-Trimethoxybenzaldehyde 45V, Positive-QTOF	splash10-0fri-0900000000-ed68bccb045f71bf1c6b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,4,5-Trimethoxybenzaldehyde 75V, Positive-QTOF	splash10-0079-1900000000-1a464f4bb537ca9f0ee0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,4,5-Trimethoxybenzaldehyde 60V, Positive-QTOF	splash10-000i-0900000000-d3a9cdd3b87f42a72701	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,4,5-Trimethoxybenzaldehyde 60V, Negative-QTOF	splash10-014i-0900000000-a42d8fcb58c07b171fc7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,4,5-Trimethoxybenzaldehyde 75V, Negative-QTOF	splash10-014i-0900000000-57c5023c73fcae020fa1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,4,5-Trimethoxybenzaldehyde 45V, Negative-QTOF	splash10-014i-0900000000-c078b44e474abe35e8bd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,4,5-Trimethoxybenzaldehyde 90V, Positive-QTOF	splash10-022i-4900000000-b492f1f12eef42776a97	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,4,5-Trimethoxybenzaldehyde 15V, Negative-QTOF	splash10-03di-0900000000-59950d21635fac255049	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,4,5-Trimethoxybenzaldehyde 30V, Negative-QTOF	splash10-0002-0900000000-d0cf99236d2033e2c995	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,4,5-Trimethoxybenzaldehyde 90V, Negative-QTOF	splash10-014i-2900000000-5ea7ee450ca95d0711eb	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,5-Trimethoxybenzaldehyde 10V, Positive-QTOF	splash10-0002-0900000000-feb0d1ef26e29da05c1f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,5-Trimethoxybenzaldehyde 20V, Positive-QTOF	splash10-0002-0900000000-200a79385d3c50f3bff5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,5-Trimethoxybenzaldehyde 40V, Positive-QTOF	splash10-1010-1900000000-1c32fe7293f3e653cc05	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,5-Trimethoxybenzaldehyde 10V, Negative-QTOF	splash10-0002-0900000000-9745902f80ca746e5fdf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,5-Trimethoxybenzaldehyde 20V, Negative-QTOF	splash10-0002-0900000000-a3c6e5ed373dd3ea0763	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4,5-Trimethoxybenzaldehyde 40V, Negative-QTOF	splash10-052b-7900000000-df74e3367cbf56205613	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB000819

KNApSAcK ID

C00036456

Chemspider ID

19331

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20525

PDB ID

Not Available

ChEBI ID

745413

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1011321

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 2,4,5-Trimethoxybenzaldehyde (HMDB0029648)

MOL for HMDB0029648 (2,4,5-Trimethoxybenzaldehyde)

3D MOL for HMDB0029648 (2,4,5-Trimethoxybenzaldehyde)

3D SDF for HMDB0029648 (2,4,5-Trimethoxybenzaldehyde)

3D-SDF for HMDB0029648 (2,4,5-Trimethoxybenzaldehyde)

PDB for HMDB0029648 (2,4,5-Trimethoxybenzaldehyde)

3D PDB for HMDB0029648 (2,4,5-Trimethoxybenzaldehyde)

SMILES for HMDB0029648 (2,4,5-Trimethoxybenzaldehyde)

INCHI for HMDB0029648 (2,4,5-Trimethoxybenzaldehyde)

Structure for HMDB0029648 (2,4,5-Trimethoxybenzaldehyde)

3D Structure for HMDB0029648 (2,4,5-Trimethoxybenzaldehyde)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra