AFCDB: Homovanillin (FDB023632)

Record Information

Version

1.0

Creation date

2011-09-21 00:32:41 UTC

Update date

2015-07-21 06:57:48 UTC

Primary ID

FDB023632

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Homovanillin

Description

Homovanillin, also known as HMPAL, 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. Homovanillin is an extremely weak basic (essentially neutral) compound (based on its pKa). Homovanillin exists in all living organisms, ranging from bacteria to humans. Homovanillin is a floral and vanilla tasting compound.

CAS Number

5703-24-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.9 g/L	ALOGPS
logP	1.52	ALOGPS
logP	0.99	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	9.94	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	44.88 m³·mol⁻¹	ChemAxon
Polarizability	16.81 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

Chemical Formula

C9H10O3

IUPAC name

2-(4-hydroxy-3-methoxyphenyl)acetaldehyde

InChI Identifier

InChI=1S/C9H10O3/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,5-6,11H,4H2,1H3

InChI Key

GOQGGGANVKPMNH-UHFFFAOYSA-N

Isomeric SMILES

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

Average Molecular Weight

166.1739

Monoisotopic Molecular Weight

166.062994186

Classification

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
Phenylacetaldehyde
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Alpha-hydrogen aldehyde
Ether
Aldehyde
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

alpha-CH2-containing aldehyde (CHEBI:28111 )
phenylacetaldehydes (CHEBI:28111 )

Ontology

Disposition

Biological location:

Subcellular:

Cytoplasm

Source:

Endogenous

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Homovanillin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0079-1900000000-e28b59106188528267be	Spectrum
Predicted GC-MS	Homovanillin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-6970000000-a597b09f1ff1acebbc8a	Spectrum
Predicted GC-MS	Homovanillin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Homovanillin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-d1e8f15334f430895ace	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014s-1900000000-e7c5332202c6a2921d0b	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-9500000000-8692ad76fd38a1c456dc	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-5560a290417d5b338a9f	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-ecdd9295a0eb88d0d20c	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9600000000-3121b7d402f23864e3a8	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0900000000-a06af236d75a4fe9514a	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-1900000000-824acd5fd49e69091de8	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-9600000000-55f5cc9088e21fdfd192	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01bi-0900000000-15f57513fdfffda8fc45	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-abbd129d0f4894a88d6a	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9100000000-f583c2db9bbeb78e47be	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

133331

ChEMBL ID

Not Available

KEGG Compound ID

C05581

Pubchem Compound ID

151276

Pubchem Substance ID

Not Available

ChEBI ID

28111

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB05175

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

46064

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1055621

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Tyrosine Metabolism	SMP00006	map00350

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
floral	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
vanilla	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Homovanillin (FDB023632)

Structure for FDB023632 (Homovanillin)