Vanillin (YMDB01803)

Identification

YMDB ID

YMDB01803

Name

Vanillin

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Vanillin, also known as vanillaldehyde or 5-bromovanillin, 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. Vanillin exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on Vanillin.

Structure

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

Synonyms

4-Hydroxy-3-methoxybenzaldehyde
5-Bromovanillin
5-Chlorovanillin
Vanillaldehyde
Vanillin, sodium salt
3-Methoxy-4-hydroxybenzaldehyde
4-Formyl-2-methoxyphenol
4-Hydroxy-3-methoxy-benzaldehyde
4-Hydroxy-m-anisaldehyde
Methylprotocatechuic aldehyde
p-Hydroxy-m-methoxybenzaldehyde
p-Vanillin
Vaniline
Vanillic aldehyde
2-Methoxy-4-formylphenol
4-Hydroxy 3-methoxybenzaldehyde
4-Hydroxy-3-methoxy-benzaldehyde-5-chlorovanillin
4-Hydroxy-3-methoxybenzaldehyde (acd/name 4.0)
4-Hydroxy-5-methoxybenzaldehyde
Lioxin
m-Methoxy-p-hydroxybenzaldehyde
Methyl-protocatechualdehyde
Methylprotcatechuic aldehyde
oleo-Resins vanilla
oleo-Resins vanilla-bean
Oleoresin vanilla
Propenylguaethol
Protocatechualdehyde 3-methyl ether
trans-2-Ethoxy-5-(1-propenyl)phenol
Vanilin
Vanilla
Vanilla oleoresin
Vanillin (3-methoxy-4-hydroxy- benzaldehyde)
Vanillin (natural)
Vanillin (NF)
Vanillin sodium salt
Vanilline
Zimco
4-Hydroxy-3-methoxy-benzyldehyde
Vanillum
Vanillin

CAS number

121-33-5

Weight

Average: 152.1473
Monoisotopic: 152.047344122

InChI Key

MWOOGOJBHIARFG-UHFFFAOYSA-N

InChI

InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3

IUPAC Name

4-hydroxy-3-methoxybenzaldehyde

Traditional IUPAC Name

vanillin

Chemical Formula

C₈H₈O₃

SMILES

COC1=CC(C=O)=CC=C1O

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

Methoxyphenol
Hydroxybenzaldehyde
Anisole
Benzaldehyde
Benzoyl
Phenoxy compound
Phenol ether
Methoxybenzene
Alkyl aryl ether
Aryl-aldehyde
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Ether
Organooxygen compound
Aldehyde
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:18346 )
monomethoxybenzene (CHEBI:18346 )
benzaldehydes (CHEBI:18346 )
a small molecule (VANILLIN )

Physical Properties

State

Solid

Charge

Melting point

81.5 °C

Experimental Properties

Property	Value	Reference
Water Solubility	11 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	1.21 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	5.05 g/L	ALOGPS
logP	1.31	ALOGPS
logP	1.22	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	7.81	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	2	ChemAxon
Refractivity	41.09 m³·mol⁻¹	ChemAxon
Polarizability	14.82 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
Chocolate	FDB000838
Creamy	FDB000838
Sweet	FDB000838
Vanilla	FDB000838

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)	splash10-0udi-1900000000-46e0edb3260b8896145e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udi-7900000000-ee0a0ad1232fa889e567	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udi-9800000000-d8f749f48a78e7c9c3bf	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-1960000000-b6678c7961ee7df779a1	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udi-1900000000-46e0edb3260b8896145e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udi-7900000000-ee0a0ad1232fa889e567	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udi-9800000000-d8f749f48a78e7c9c3bf	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-1960000000-b6678c7961ee7df779a1	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fk9-1900000000-68ebbe847e88a001f8fa	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-7950000000-08c9e1cb0dbb3704f8ee	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-0udi-0900000000-334e2cf1c60f75229fd1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-0uy0-0900200200-4cbd13b45290ded181ee	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udr-0900000000-d67b08f1b4f6e90cd270	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-1900000000-9fc5182650ced222b1a1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-052b-9800000000-312c82e1fbcda8abeaf7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-0a4j-9700000000-c0da5ed12872161ea30e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000l-5900000000-8c4d3cd8abfc264729a3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-a9b7f966d85c30f6174c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-d1e812bea83f6f84570d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000f-7900000000-9d9283afc35603b0121c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9000000000-146c4b184605c821d822	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00kf-9500000000-f5a8328127a89c12c19e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-014i-9000000000-44efadd4b0c1fe89c39c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9100000000-70cac2e87a3ecb4ec867	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-0udr-0900000000-10b0539cab1169d8d877	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-0900000000-17943fa1f4f19dd4878a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0udr-0900000000-2e50ec52313e18cddbd0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-0f79-1900000000-98d502286eb47c703f64	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-052e-9800000000-03597a1112a480b91d5e	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-e949414f752aab5e9606	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-1dcee0be3ba8e1431a7c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ff9-9400000000-dcd0372357bd9c46926d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-6cc5e0ed993af0b790e6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1900000000-cf1b6af77251971154f9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000l-9500000000-302ce8740fbb7b9295b9	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-5900000000-907c9684d5ac0386d522	JSpectraViewer \| MoNA
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:

Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). "Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions." J Agric Food Chem 55:6674-6684.17616208
Chatonnet, P., Dubourdieu, D., & Boidron, J. N. (1992a) Incidence des conditions de fermentation et d’elevage des vins blanc secs en barriques sur leur composition en substances cedees par le bois de chene. Science des Aliments, 12, 665–685.

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	18346
HMDB ID	HMDB12308
Pubchem Compound ID	1183
Kegg ID	C00755
ChemSpider ID	13860434
FOODB ID	FDB000838
Wikipedia ID	Vanillin
BioCyc ID	Not Available

Structure for #<Compound:0xa131981c>