MiMeDB: Showing metabocard for Ethyl vanillin (MMDBc0033636)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:56:54 UTC

Update Date

2024-09-29 05:02:12 UTC

Metabolite ID

MMDBc0033636

Metabolite Identification

Common Name

Ethyl vanillin

Description

Ethyl vanillin is a flavouring agent with flavouring power 2-4 times greater than vanillin. Ethyl vanillin is used especially in cocoa product

Structure

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

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   12                                                       
CONECT    3    4    7                                                       
CONECT    4    3    8                                                       
CONECT    5    7    9                                                       
CONECT    6    7   10                                                       
CONECT    7    3    5    6                                                  
CONECT    8    4    9   11                                                  
CONECT    9    5    8   12                                                  
CONECT   10    6                                                            
CONECT   11    8                                                            
CONECT   12    2    9                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

Synonyms

Value	Source
2-Ethoxy-4-formylphenol	ChEBI
3-Ethoxyprotocatechualdehyde	ChEBI
4-Hydroxy-3-ethoxybenzaldehyde	ChEBI
Bourbonal	ChEBI
Ethyl protal	ChEBI
Vanilal	ChEBI
3-Ethoxy-4-hydroxybenzaldehyde	MeSH
3-ETHOXY-4-hydroxy-benzaldehyde	HMDB
Aethylvanillin	HMDB
Ethavan	HMDB
Ethovan	HMDB
Ethyl proto-catechualdehyde-3-ethyl ether	HMDB
Ethyl protocatechualdehyde	HMDB
Ethyl vanillin (NF)	HMDB
Ethyl vanillin, usan?	HMDB
Ethyl-vanillin	HMDB
Ethylprotal	HMDB
Ethylprotocatechualdehyde-3-ethyl ether	HMDB
Ethylprotocatechuic aldehyde	HMDB
Ethylvanillin	HMDB
FEMA 2464	HMDB
Protocatechuic aldehyde 3-ethyl ether	HMDB
Protocatechuic aldehyde ethyl ether	HMDB
Quantrovanil	HMDB
Quantrovanil, vanillal	HMDB
Rhodiarome	HMDB
Vanbeenol	HMDB
Vanillal	HMDB
Vanirom	HMDB
Vanirome	HMDB

Molecular Formula

C₉H₁₀O₃

Average Mass

166.1739

Monoisotopic Mass

166.062994186

IUPAC Name

3-ethoxy-4-hydroxybenzaldehyde

Traditional Name

ethyl vanillin

CAS Registry Number

121-32-4

SMILES

CCOC1=C(O)C=CC(C=O)=C1

InChI Identifier

InChI=1S/C9H10O3/c1-2-12-9-5-7(6-10)3-4-8(9)11/h3-6,11H,2H2,1H3

InChI Key

CBOQJANXLMLOSS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Hydroxybenzaldehydes

Alternative Parents

Substituents

Hydroxybenzaldehyde
Phenoxy compound
Phenol ether
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Ether
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:48408 )
phenols (CHEBI:48408 )
benzaldehydes (CHEBI:48408 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.72 g/L	ALOGPS
logP	1.82	ALOGPS
logP	1.58	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	7.79	ChemAxon
pKa (Strongest Basic)	-4.9	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	45.83 m³·mol⁻¹	ChemAxon
Polarizability	17 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-7900000000-82021b1b58fb03cd9cc6	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-8900000000-120b162ff2c185f413bb	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-4900000000-5cc4d780ed9e9279561d	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-7900000000-82021b1b58fb03cd9cc6	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-8900000000-120b162ff2c185f413bb	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-4900000000-5cc4d780ed9e9279561d	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0900000000-afc9dd7ed64604d0102f	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-4950000000-a33f56f4bc60325bef65	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-014r-1900000000-7731b0038b523b919463	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-014r-1900000000-8df27c702ca0792480d1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-0006-9400000000-f2fc05096f0752c35b85	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-000l-6900000000-bfaf6c2a0d0819eff8d9	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-0006-9100000000-b60e34d7d812476e3976	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-0006-9200000000-301672a18e1b7b1a036b	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-89239990c4a10955d988	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014r-1900000000-5c128876e8bad02cc839	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fu-9700000000-bf41857855baca586fed	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-6b1cd6daa42968b433bc	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014r-1900000000-270e0adeb0ef058d650d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052s-9700000000-34282a16d387610767af	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-eab654448b8a4a51a1c6	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052r-0900000000-5d7d62f2d4ae53ba017f	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9500000000-b30c8cfc66d63ac1989c	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-89f6c95a9e36813efac2	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1900000000-751f2c2b53ed77f719ae	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00o0-9200000000-3f9070e823d202f2c5aa	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)		2016-09-19	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)		2016-09-19	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0029665

DrugBank ID

Not Available

Phenol Explorer Compound ID

728

FooDB ID

FDB000841

KNApSAcK ID

Not Available

Chemspider ID

8154

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ethylvanillin

METLIN ID

Not Available

PubChem Compound

8467

PDB ID

Not Available

ChEBI ID

48408

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Jansson T, Curvall M, Hedin A, Enzell CR: In vitro studies of the biological effects of cigarette smoke condensate. III. Induction of SCE by some phenolic and related constituents derived from cigarette smoke. A study of structure-activity relationships. Mutat Res. 1988 Sep;206(1):17-24. doi: 10.1016/0165-1218(88)90136-x. [PubMed:3412370 ]
Ohta T, Watanabe M, Watanabe K, Shirasu Y, Kada T: Inhibitory effects of flavourings on mutagenesis induced by chemicals in bacteria. Food Chem Toxicol. 1986 Jan;24(1):51-4. doi: 10.1016/0278-6915(86)90264-4. [PubMed:3512393 ]
Sasaki YuF, Imanishi H, Ohta T, Shirasu Y: Effects of antimutagenic flavourings on SCEs induced by chemical mutagens in cultured Chinese hamster cells. Mutat Res. 1987 Nov;189(3):313-8. doi: 10.1016/0165-1218(87)90063-2. [PubMed:3670335 ]
Shimada M, Habe T, Umezawa T, Higuchi T, Okamoto T: The C-C bond cleavage of a lignin model compound, 1,2-diarylpropane-1,3-diol, with a heme-enzyme model catalyst tetraphenylporphyrinatoiron(III)chloride in the presence of tert-butylhydroperoxide. Biochem Biophys Res Commun. 1984 Aug 16;122(3):1247-52. doi: 10.1016/0006-291x(84)91226-9. [PubMed:6477560 ]
CAUJOLLE F, MEYNIER D: [Toxicity of vanillin, o-vanillin, ethylvanillin and the corresponding isophthalaldehydes]. Ann Pharm Fr. 1954 Jan;12(1):42-9. [PubMed:13171720 ]
CAUJOLLE F, MEYNIER D: [Effects of vanillin, orthovanillin, ethylvanillin and their corresponding dialdehydes on smooth muscle fibers]. Ann Pharm Fr. 1954 Jun;12(6):448-58. [PubMed:13229068 ]
DESHUSSES J, DESBAUMES P: [Paper chromatography of vanillin and ethylvanillin in food stuffs]. Mitt Geb Lebensmittelunters Hyg. 1957;48(2):49-58. [PubMed:13464725 ]
HALD JG: [Detection of 2-alkoxyphenols in vanillin and ethylvanillin]. Dan Tidsskr Farm. 1961 Apr;35:73-7. [PubMed:13710686 ]
WOGGON H, KOEHLER U: [Paper chromato-oscillopolarographic determination of vanillin and ethylvanillin in food]. Ernahrungsforsch Ber Mitt. 1960;5:402-9. [PubMed:13786183 ]
PROFFT E, STEINKE U: [ON ETHYLVANILLIN. I]. Arch Pharm Ber Dtsch Pharm Ges. 1964 May;297:282-91. doi: 10.1002/ardp.19642970505. [PubMed:14243749 ]
PROFFT E, STEINKE U: [ON ETHYLVANILLIN. II]. Arch Pharm Ber Dtsch Pharm Ges. 1964 May;297:292-8. doi: 10.1002/ardp.19642970506. [PubMed:14243750 ]
Fujioka K, Shibamoto T: Improved malonaldehyde assay using headspace solid-phase microextraction and its application to the measurement of the antioxidant activity of phytochemicals. J Agric Food Chem. 2005 Jun 15;53(12):4708-13. doi: 10.1021/jf050297q. [PubMed:15941304 ]
Ohashi M, Omae H, Hashida M, Sowa Y, Imai S: Determination of vanillin and related flavor compounds in cocoa drink by capillary electrophoresis. J Chromatogr A. 2007 Jan 5;1138(1-2):262-7. doi: 10.1016/j.chroma.2006.10.031. Epub 2006 Nov 7. [PubMed:17084851 ]
Rhee YS, Shin YH, Park CW, Chi SC, Park ES: Effect of flavors on the viscosity and gelling point of aqueous poloxamer solution. Arch Pharm Res. 2006 Dec;29(12):1171-8. doi: 10.1007/BF02969310. [PubMed:17225469 ]
Kahoun D, Rezkova S, Veskrnova K, Kralovsky J, Holcapek M: Determination of phenolic compounds and hydroxymethylfurfural in meads using high performance liquid chromatography with coulometric-array and UV detection. J Chromatogr A. 2008 Aug 15;1202(1):19-33. doi: 10.1016/j.chroma.2008.06.016. Epub 2008 Jun 18. [PubMed:18620360 ]
Timotheou-Potamia M, Calokerinos AC: Chemiluminometric determination of vanillin in commercial vanillin products. Talanta. 2007 Jan 15;71(1):208-12. doi: 10.1016/j.talanta.2006.03.046. Epub 2006 Jun 19. [PubMed:19071290 ]
Lima DL, Duarte AC, Esteves VI: Optimization of phenolic compounds analysis by capillary electrophoresis. Talanta. 2007 Jun 15;72(4):1404-9. doi: 10.1016/j.talanta.2007.01.049. Epub 2007 Jan 30. [PubMed:19071776 ]
Zech M, Glaser B: Compound-specific delta18O analyses of neutral sugars in soils using gas chromatography-pyrolysis-isotope ratio mass spectrometry: problems, possible solutions and a first application. Rapid Commun Mass Spectrom. 2009 Nov;23(22):3522-32. doi: 10.1002/rcm.4278. [PubMed:19844972 ]
Cocinero EJ, Lesarri A, Ecija P, Grabow JU, Fernandez JA, Castano F: Conformational equilibria in vanillin and ethylvanillin. Phys Chem Chem Phys. 2010 Oct 21;12(39):12486-93. doi: 10.1039/c0cp00585a. Epub 2010 Aug 19. [PubMed:20721403 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for Ethyl vanillin (MMDBc0033636)

MOL for #<Metabolite:0x00007f47053e75d0>

3D MOL for #<Metabolite:0x00007f47053e75d0>

3D SDF for #<Metabolite:0x00007f47053e75d0>

3D-SDF for #<Metabolite:0x00007f47053e75d0>

PDB for #<Metabolite:0x00007f47053e75d0>

3D PDB for #<Metabolite:0x00007f47053e75d0>

SMILES for #<Metabolite:0x00007f47053e75d0>

INCHI for #<Metabolite:0x00007f47053e75d0>

Structure for #<Metabolite:0x00007f47053e75d0>

3D Structure for #<Metabolite:0x00007f47053e75d0>