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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:56:15 UTC

Update Date

2023-02-21 17:26:59 UTC

HMDB ID

HMDB0039471

Secondary Accession Numbers

HMDB39471

Metabolite Identification

Common Name

3-(4-Hydroxy-2-methoxyphenyl)-2-propenal

Description

3-(4-Hydroxy-2-methoxyphenyl)-2-propenal belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 3-(4-Hydroxy-2-methoxyphenyl)-2-propenal has been detected, but not quantified in, fats and oils and herbs and spices. This could make 3-(4-hydroxy-2-methoxyphenyl)-2-propenal a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-(4-Hydroxy-2-methoxyphenyl)-2-propenal.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2    3    6                                                       
CONECT    3    2    8                                                       
CONECT    4    5    8                                                       
CONECT    5    4    9                                                       
CONECT    6    2   11                                                       
CONECT    7    9   10                                                       
CONECT    8    3    4   10                                                  
CONECT    9    5    7   12                                                  
CONECT   10    7    8   13                                                  
CONECT   11    6                                                            
CONECT   12    9                                                            
CONECT   13    1   10                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2E)-3-(4-Hydroxy-2-methoxyphenyl)-2-propenal	HMDB
4-Hydroxy-2-methoxycinnamaldehyde	HMDB
Ethyl 3-(4-methyl-2-oxo-1(2H)-quinolinyl)acrylate	HMDB

Chemical Formula

C₁₀H₁₀O₃

Average Molecular Weight

178.1846

Monoisotopic Molecular Weight

178.062994186

IUPAC Name

(2E)-3-(4-hydroxy-2-methoxyphenyl)prop-2-enal

Traditional Name

(2E)-3-(4-hydroxy-2-methoxyphenyl)prop-2-enal

CAS Registry Number

127321-19-1

SMILES

COC1=C(\C=C\C=O)C=CC(O)=C1

InChI Identifier

InChI=1S/C10H10O3/c1-13-10-7-9(12)5-4-8(10)3-2-6-11/h2-7,12H,1H3/b3-2+

InChI Key

MRCGVXARHKOYKU-NSCUHMNNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Cinnamaldehyde
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Enal
Alpha,beta-unsaturated aldehyde
Ether
Hydrocarbon derivative
Carbonyl group
Aldehyde
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039471)
Cytoplasm (HMDB: HMDB0039471)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039471)

Source

Exogenous

Food

Food (HMDB: HMDB0039471)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Plant

Plant (HMDB: HMDB0039471)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0039471)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.42 g/L	ALOGPS
logP	2.18	ALOGPS
logP	1.52	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	9.12	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	50.58 m³·mol⁻¹	ChemAxon
Polarizability	18.32 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
DeepCCS	[M+H]+	138.87	30932474
DeepCCS	[M-H]-	136.213	30932474
DeepCCS	[M-2H]-	171.939	30932474
DeepCCS	[M+Na]+	147.333	30932474
AllCCS	[M+H]+	138.3	32859911
AllCCS	[M+H-H2O]+	134.0	32859911
AllCCS	[M+NH4]+	142.3	32859911
AllCCS	[M+Na]+	143.5	32859911
AllCCS	[M-H]-	137.4	32859911
AllCCS	[M+Na-2H]-	138.2	32859911
AllCCS	[M+HCOO]-	139.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-(4-Hydroxy-2-methoxyphenyl)-2-propenal	COC1=C(\C=C\C=O)C=CC(O)=C1	2707.1	Standard polar	33892256
3-(4-Hydroxy-2-methoxyphenyl)-2-propenal	COC1=C(\C=C\C=O)C=CC(O)=C1	1723.5	Standard non polar	33892256
3-(4-Hydroxy-2-methoxyphenyl)-2-propenal	COC1=C(\C=C\C=O)C=CC(O)=C1	1837.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-(4-Hydroxy-2-methoxyphenyl)-2-propenal,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC=C1/C=C/C=O	1905.3	Semi standard non polar	33892256
3-(4-Hydroxy-2-methoxyphenyl)-2-propenal,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1/C=C/C=O	2194.7	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 - 3-(4-Hydroxy-2-methoxyphenyl)-2-propenal GC-MS (Non-derivatized) - 70eV, Positive	splash10-002b-0900000000-406ccc93ff248c6fd22d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(4-Hydroxy-2-methoxyphenyl)-2-propenal GC-MS (1 TMS) - 70eV, Positive	splash10-00dr-4390000000-f9767465b7b96af1b791	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(4-Hydroxy-2-methoxyphenyl)-2-propenal 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 - 3-(4-Hydroxy-2-methoxyphenyl)-2-propenal 10V, Positive-QTOF	splash10-004i-0900000000-daf7806fc3bb9d0672e2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Hydroxy-2-methoxyphenyl)-2-propenal 20V, Positive-QTOF	splash10-01t9-2900000000-eea103518c15d73cff51	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Hydroxy-2-methoxyphenyl)-2-propenal 40V, Positive-QTOF	splash10-0aor-8900000000-af5a0b6106c61ec5ede7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Hydroxy-2-methoxyphenyl)-2-propenal 10V, Negative-QTOF	splash10-004i-0900000000-4f9e997e639aac6778ee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Hydroxy-2-methoxyphenyl)-2-propenal 20V, Negative-QTOF	splash10-004i-0900000000-0f5df277cad9ca46343c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Hydroxy-2-methoxyphenyl)-2-propenal 40V, Negative-QTOF	splash10-0536-9700000000-6ccba7201b39419fa52d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Hydroxy-2-methoxyphenyl)-2-propenal 10V, Positive-QTOF	splash10-004i-0900000000-2e7e9542a59b5a98d406	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Hydroxy-2-methoxyphenyl)-2-propenal 20V, Positive-QTOF	splash10-000i-1900000000-744666d0898859945c6c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Hydroxy-2-methoxyphenyl)-2-propenal 40V, Positive-QTOF	splash10-0a4i-6900000000-70163627963e310af849	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Hydroxy-2-methoxyphenyl)-2-propenal 10V, Negative-QTOF	splash10-004i-0900000000-de62e841e9f1301230c2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Hydroxy-2-methoxyphenyl)-2-propenal 20V, Negative-QTOF	splash10-009t-0900000000-1317c770805f81952dd5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Hydroxy-2-methoxyphenyl)-2-propenal 40V, Negative-QTOF	splash10-00o0-1900000000-64fd1970df4a9f248f41	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+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

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

FDB019075

KNApSAcK ID

Not Available

Chemspider ID

4524357

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5374604

PDB ID

Not Available

ChEBI ID

Not Available

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

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

Showing metabocard for 3-(4-Hydroxy-2-methoxyphenyl)-2-propenal (HMDB0039471)

MOL for HMDB0039471 (3-(4-Hydroxy-2-methoxyphenyl)-2-propenal)

3D MOL for HMDB0039471 (3-(4-Hydroxy-2-methoxyphenyl)-2-propenal)

3D SDF for HMDB0039471 (3-(4-Hydroxy-2-methoxyphenyl)-2-propenal)

3D-SDF for HMDB0039471 (3-(4-Hydroxy-2-methoxyphenyl)-2-propenal)

PDB for HMDB0039471 (3-(4-Hydroxy-2-methoxyphenyl)-2-propenal)

3D PDB for HMDB0039471 (3-(4-Hydroxy-2-methoxyphenyl)-2-propenal)

SMILES for HMDB0039471 (3-(4-Hydroxy-2-methoxyphenyl)-2-propenal)

INCHI for HMDB0039471 (3-(4-Hydroxy-2-methoxyphenyl)-2-propenal)

Structure for HMDB0039471 (3-(4-Hydroxy-2-methoxyphenyl)-2-propenal)

3D Structure for HMDB0039471 (3-(4-Hydroxy-2-methoxyphenyl)-2-propenal)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra