Ethyl vanillin (YMDB01687)

Identification

YMDB ID

YMDB01687

Name

Ethyl vanillin

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Ethyl vanillin, also known as bourbonal or ethyl protal, 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. Based on a literature review a significant number of articles have been published on Ethyl vanillin.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

3-Ethoxy-4-hydroxybenzaldehyde
3-methoxy-4-hydroxybenzaldehyde
4-formyl-2-methoxyphenol
4-Hydroxy-3-ethoxybenzaldehyde
4-Hydroxy-3-methoxy-benzaldehyde
4-Hydroxy-3-methoxybenzaldehyde
4-hydroxy-m-anisaldehyde
Benzaldehyde, 3-ethoxy-4-hydroxy-
Bourbonal
Ethavan
Ethovan
Ethyl proto-catechualdehyde-3-ethyl ether
Ethyl protocatechualdehyde
Ethyl vanillin (NF)
Ethylprotal
Ethylprotocatechuic aldehyde
Ethylvanillin
methylprotocatechuic aldehyde
p-hydroxy-m-methoxybenzaldehyde
p-vanillin
Protocatechuic aldehyde 3-ethyl ether
Protocatechuic aldehyde ethyl ether
Quantrovanil
Rhodiarome
Vanbeenol
Vanilal
vaniline
Vanillal
Vanillaldehyde
vanillic aldehyde
Vanillin
Vanillin, ethyl-
Vanirom
2-Ethoxy-4-formylphenol
3-Ethoxyprotocatechualdehyde
Ethyl protal
3-ETHOXY-4-hydroxy-benzaldehyde
Aethylvanillin
Ethyl vanillin, usan?
Ethyl-vanillin
Ethylprotocatechualdehyde-3-ethyl ether
FEMA 2464
Quantrovanil, vanillal
Vanirome

CAS number

121-32-4

Weight

Average: 166.1739
Monoisotopic: 166.062994186

InChI Key

CBOQJANXLMLOSS-UHFFFAOYSA-N

InChI

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

IUPAC Name

3-ethoxy-4-hydroxybenzaldehyde

Traditional IUPAC Name

ethyl vanillin

Chemical Formula

C₉H₁₀O₃

SMILES

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

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 )

Physical Properties

State

Solid

Charge

Melting point

77.5 °C

Experimental Properties

Property	Value	Reference
Water Solubility	2.82 mg/mL at 25 oC [JIN,LJ et al. (1998)]	PhysProp
LogP	1.58 [BAZACO,JF & COCA,CM (1989)]	PhysProp

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Flavour/Odour	Source
Caramel	FDB000841
Creamy	FDB000841
Sweet	FDB000841
Vanilla	FDB000841

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-7900000000-82021b1b58fb03cd9cc6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-8900000000-120b162ff2c185f413bb	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-4900000000-5cc4d780ed9e9279561d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-7900000000-82021b1b58fb03cd9cc6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-8900000000-120b162ff2c185f413bb	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-4900000000-5cc4d780ed9e9279561d	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0900000000-afc9dd7ed64604d0102f	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-4950000000-a33f56f4bc60325bef65	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-014r-1900000000-7731b0038b523b919463	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-014r-1900000000-8df27c702ca0792480d1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-0006-9400000000-f2fc05096f0752c35b85	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-000l-6900000000-bfaf6c2a0d0819eff8d9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-0006-9100000000-b60e34d7d812476e3976	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-0006-9200000000-301672a18e1b7b1a036b	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-89239990c4a10955d988	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014r-1900000000-5c128876e8bad02cc839	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fu-9700000000-bf41857855baca586fed	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-6b1cd6daa42968b433bc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014r-1900000000-270e0adeb0ef058d650d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052s-9700000000-34282a16d387610767af	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-eab654448b8a4a51a1c6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052r-0900000000-5d7d62f2d4ae53ba017f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9500000000-b30c8cfc66d63ac1989c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-89f6c95a9e36813efac2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1900000000-751f2c2b53ed77f719ae	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00o0-9200000000-3f9070e823d202f2c5aa	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	48408
HMDB ID	HMDB0029665
Pubchem Compound ID	8467
Kegg ID	Not Available
ChemSpider ID	8154
FOODB ID	FDB000841
Wikipedia ID	Ethylvanillin
BioCyc ID	Not Available

Structure for #<Compound:0xa8bded4c>