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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:32:03 UTC

Update Date

2023-02-21 17:19:02 UTC

HMDB ID

HMDB0029685

Secondary Accession Numbers

HMDB29685

Metabolite Identification

Common Name

4-Ethoxy-3-methoxybenzaldehyde

Description

4-Ethoxy-3-methoxybenzaldehyde, also known as 4-ethoxy-3-anisaldehyde or ethylvanillin?, 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 very few articles have been published on 4-Ethoxy-3-methoxybenzaldehyde.

Structure

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

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0      -2.773   3.466   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.231   2.695   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.231   1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.464   0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.464  -1.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.231  -1.925   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.154  -1.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.154   0.385   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.540   1.155   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.773   1.925   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.851   1.155   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.851  -1.925   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.851  -3.466   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    3    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    5   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Ethoxy-3-anisaldehyde	HMDB
4-Ethoxy-3-methoxy-benzaldehyde	HMDB
4-Ethoxy-m-anisaldehyde	HMDB
Ethylvanillin?	HMDB

Chemical Formula

C₁₀H₁₂O₃

Average Molecular Weight

180.2005

Monoisotopic Molecular Weight

180.07864425

IUPAC Name

4-ethoxy-3-methoxybenzaldehyde

Traditional Name

ethyl-vanillin

CAS Registry Number

120-25-2

SMILES

CCOC1=CC=C(C=O)C=C1OC

InChI Identifier

InChI=1S/C10H12O3/c1-3-13-9-5-4-8(7-11)6-10(9)12-2/h4-7H,3H2,1-2H3

InChI Key

BERFDQAMXIBOHM-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

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029685)
Cytoplasm (HMDB: HMDB0029685)

Source

Endogenous

Endogenous (HMDB: HMDB0029685)

Exogenous

Food

Food (HMDB: HMDB0029685)

Exogenous (HMDB: HMDB0029685)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	64 - 65 °C	Not Available
Boiling Point	288.00 to 289.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1.16 mg/mL at 25 °C	Not Available
LogP	1.63	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.67 g/L	ALOGPS
logP	2.18	ALOGPS
logP	1.73	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	50.32 m³·mol⁻¹	ChemAxon
Polarizability	19.01 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	139.999	31661259
DarkChem	[M-H]-	138.842	31661259
DeepCCS	[M+H]+	137.867	30932474
DeepCCS	[M-H]-	134.04	30932474
DeepCCS	[M-2H]-	171.575	30932474
DeepCCS	[M+Na]+	147.113	30932474
AllCCS	[M+H]+	139.0	32859911
AllCCS	[M+H-H2O]+	134.7	32859911
AllCCS	[M+NH4]+	143.0	32859911
AllCCS	[M+Na]+	144.1	32859911
AllCCS	[M-H]-	140.2	32859911
AllCCS	[M+Na-2H]-	141.1	32859911
AllCCS	[M+HCOO]-	142.2	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. Predicted by Afia on May 17, 2022.	4.78 minutes	32390414
Predicted by Siyang on May 30, 2022	13.9274 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.36 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1761.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	461.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	166.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	266.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	104.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	517.8 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	659.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	135.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1137.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	398.0 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	1303.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	375.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	422.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	477.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	535.1 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	86.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Ethoxy-3-methoxybenzaldehyde	CCOC1=CC=C(C=O)C=C1OC	2378.3	Standard polar	33892256
4-Ethoxy-3-methoxybenzaldehyde	CCOC1=CC=C(C=O)C=C1OC	1470.0	Standard non polar	33892256
4-Ethoxy-3-methoxybenzaldehyde	CCOC1=CC=C(C=O)C=C1OC	1512.4	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 - 4-Ethoxy-3-methoxybenzaldehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uk9-0900000000-ab10a8073d1960169968	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ethoxy-3-methoxybenzaldehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ethoxy-3-methoxybenzaldehyde 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 - 4-Ethoxy-3-methoxybenzaldehyde 10V, Positive-QTOF	splash10-001i-0900000000-c7e3add2c9c5680438a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-3-methoxybenzaldehyde 20V, Positive-QTOF	splash10-001i-0900000000-5a68ed682ab5593909ba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-3-methoxybenzaldehyde 40V, Positive-QTOF	splash10-0019-5900000000-be4aa395da71a2512abe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-3-methoxybenzaldehyde 10V, Negative-QTOF	splash10-004i-0900000000-fd265b21a250320b550b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-3-methoxybenzaldehyde 20V, Negative-QTOF	splash10-0fi0-1900000000-49b026dee8dfccd070d5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-3-methoxybenzaldehyde 40V, Negative-QTOF	splash10-00kr-7900000000-f547a42c08cebefe6064	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-3-methoxybenzaldehyde 10V, Positive-QTOF	splash10-001i-0900000000-8b4036e4a37fbd1b3a5f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-3-methoxybenzaldehyde 20V, Positive-QTOF	splash10-01qi-0900000000-4cec081e27ba9be583c4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-3-methoxybenzaldehyde 40V, Positive-QTOF	splash10-001r-9700000000-314742ec3548c602ea97	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-3-methoxybenzaldehyde 10V, Negative-QTOF	splash10-004i-0900000000-09c8a2bc5613be8fd179	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-3-methoxybenzaldehyde 20V, Negative-QTOF	splash10-000i-0900000000-200dcf7817bca03bc58b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-3-methoxybenzaldehyde 40V, Negative-QTOF	splash10-00y1-9700000000-e35f99e61fc6198ca2b3	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]+)	2023-02-03	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

FDB000871

KNApSAcK ID

Not Available

Chemspider ID

60464

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

67116

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1043431

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 4-Ethoxy-3-methoxybenzaldehyde (HMDB0029685)

MOL for HMDB0029685 (4-Ethoxy-3-methoxybenzaldehyde)

3D MOL for HMDB0029685 (4-Ethoxy-3-methoxybenzaldehyde)

3D SDF for HMDB0029685 (4-Ethoxy-3-methoxybenzaldehyde)

3D-SDF for HMDB0029685 (4-Ethoxy-3-methoxybenzaldehyde)

PDB for HMDB0029685 (4-Ethoxy-3-methoxybenzaldehyde)

3D PDB for HMDB0029685 (4-Ethoxy-3-methoxybenzaldehyde)

SMILES for HMDB0029685 (4-Ethoxy-3-methoxybenzaldehyde)

INCHI for HMDB0029685 (4-Ethoxy-3-methoxybenzaldehyde)

Structure for HMDB0029685 (4-Ethoxy-3-methoxybenzaldehyde)

3D Structure for HMDB0029685 (4-Ethoxy-3-methoxybenzaldehyde)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra