Showing Compound Vanillin (FDB000838)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:44 UTC

Update date

2024-11-29 22:27:57 UTC

Primary ID

FDB000838

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Vanillin

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. Vanillin is a sweet, chocolate, and creamy tasting compound. Vanillin is found, on average, in the highest concentration within a few different foods, such as corns (Zea mays), ryes (Secale cereale), and sherry and in a lower concentration in sunflowers (Helianthus annuus), spirit, and oats (Avena sativa). Vanillin has also been detected, but not quantified in, several different foods, such as blackcurrants (Ribes nigrum), daikon radishes (Raphanus sativus var. longipinnatus), conches (Strombidae), white mustards (Sinapis alba), and fireweeds (Chamerion angustifolium). This could make vanillin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Vanillin.

CAS Number

121-33-5

Structure

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

Synonyms

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Synonym	Source
2-Methoxy-4-formylphenol	HMDB
3-Methoxy-4-hydroxybenzaldehyde	ChEBI
4-Formyl-2-methoxyphenol	ChEBI
4-Hydroxy 3-methoxybenzaldehyde	HMDB
4-Hydroxy-3-methoxy-benzaldehyde	ChEBI
4-Hydroxy-3-methoxy-benzaldehyde-5-chlorovanillin	HMDB
4-Hydroxy-3-methoxy-benzyldehyde	PhytoBank
4-Hydroxy-3-methoxybenzaldehyde	ChEBI
4-Hydroxy-3-methoxybenzaldehyde (acd/name 4.0)	HMDB
4-Hydroxy-5-methoxybenzaldehyde	HMDB

Showing 1 to 10 of 47 entries

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C8H8O3

IUPAC name

4-hydroxy-3-methoxybenzaldehyde

InChI Identifier

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

InChI Key

MWOOGOJBHIARFG-UHFFFAOYSA-N

Isomeric SMILES

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

Average Molecular Weight

152.1473

Monoisotopic Molecular Weight

152.047344122

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
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 )

Ontology

Ingestion

Biological location:

Biofluid and excreta:

Source:

Environmental:

Tobacco smoke

Biological:

Animal

Plant:

Role

Industrial application:

Food and nutrition

Foods

Cocoa and cocoa products

Grains:

Cereal products:

Whole grain cereal products

Nuts and legumes:

Fruits and vegetables:

Fats and oils:

Oils:

Vegetable oils:

Olive oil

Beverages:

Coffee products

Alcohols:

Fermented alcohols:

Wine:

Red wine

Infusions:

Tea products

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Bp15 170°	DFC
Charge	Not Available
Density	Not Available
Experimental logP	1.21	HANSCH,C ET AL. (1995)
Experimental pKa	pKa1 7.4 (25°)	DFC
Experimental Water Solubility	11 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Isoelectric point	Not Available
Mass Composition	C 63.15%; H 5.30%; O 31.55%	DFC
Melting Point	Mp 77-79° (dimorph.)	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0udi-5900000000-907c9684d5ac0386d522	2014-09-20	View Spectrum
GC-MS	Vanillin, non-derivatized, GC-MS Spectrum	splash10-0udi-1900000000-46e0edb3260b8896145e	Spectrum
GC-MS	Vanillin, non-derivatized, GC-MS Spectrum	splash10-0udi-7900000000-ee0a0ad1232fa889e567	Spectrum
GC-MS	Vanillin, non-derivatized, GC-MS Spectrum	splash10-0udi-9800000000-d8f749f48a78e7c9c3bf	Spectrum
GC-MS	Vanillin, non-derivatized, GC-MS Spectrum	splash10-00di-1960000000-b6678c7961ee7df779a1	Spectrum
GC-MS	Vanillin, non-derivatized, GC-MS Spectrum	splash10-0udi-1900000000-46e0edb3260b8896145e	Spectrum
GC-MS	Vanillin, non-derivatized, GC-MS Spectrum	splash10-0udi-7900000000-ee0a0ad1232fa889e567	Spectrum
GC-MS	Vanillin, non-derivatized, GC-MS Spectrum	splash10-0udi-9800000000-d8f749f48a78e7c9c3bf	Spectrum
GC-MS	Vanillin, non-derivatized, GC-MS Spectrum	splash10-00di-1960000000-b6678c7961ee7df779a1	Spectrum
Predicted GC-MS	Vanillin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fk9-1900000000-68ebbe847e88a001f8fa	Spectrum
Predicted GC-MS	Vanillin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05fr-7950000000-08c9e1cb0dbb3704f8ee	Spectrum
Predicted GC-MS	Vanillin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-0udi-0900000000-334e2cf1c60f75229fd1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-0uy0-0900200200-4cbd13b45290ded181ee	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udr-0900000000-d67b08f1b4f6e90cd270	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-1900000000-9fc5182650ced222b1a1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-052b-9800000000-312c82e1fbcda8abeaf7	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-0a4j-9700000000-c0da5ed12872161ea30e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000l-5900000000-8c4d3cd8abfc264729a3	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-a9b7f966d85c30f6174c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-d1e812bea83f6f84570d	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000f-7900000000-9d9283afc35603b0121c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9000000000-146c4b184605c821d822	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00kf-9500000000-f5a8328127a89c12c19e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-014i-9000000000-44efadd4b0c1fe89c39c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9100000000-70cac2e87a3ecb4ec867	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-0udr-0900000000-10b0539cab1169d8d877	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-0900000000-17943fa1f4f19dd4878a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0udr-0900000000-2e50ec52313e18cddbd0	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-0f79-1900000000-98d502286eb47c703f64	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-052e-9800000000-03597a1112a480b91d5e	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-e949414f752aab5e9606	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-1dcee0be3ba8e1431a7c	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ff9-9400000000-dcd0372357bd9c46926d	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-6cc5e0ed993af0b790e6	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1900000000-cf1b6af77251971154f9	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000l-9500000000-302ce8740fbb7b9295b9	2015-05-27	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

18346

Phenol-Explorer ID

724

DrugBank ID

Not Available

HMDB ID

HMDB12308

CRC / DFC (Dictionary of Food Compounds) ID

HCW75-Q:BJR54-T

EAFUS ID

3830

Dr. Duke ID

VANILLIC-ALDEHYDE|VANILLIN|4-HYDROXY-3-METHOXYBENZALDEHYDE

BIGG ID

Not Available

KNApSAcK ID

C00029531

HET ID

V55

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

121-33-5

GoodScent ID

rw1011711

SuperScent ID

Not Available

Wikipedia ID

Vanillin

Phenol-Explorer Metabolite ID

724

Duplicate IDS

Knapsack: C00002683

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
allelochemic			DUKE
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
anti anemic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti cancer	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti drepanocytic			DUKE
anti escherichic			DUKE
anti lactobacillic	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti listeria	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti mutagenic			DUKE
anti polio	22587	A substance that destroys or inhibits replication of viruses.	DUKE

Showing 1 to 10 of 28 entries

Enzymes

Not Available

Pathways

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Flavor	Citations
chocolate	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
creamy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
vanilla	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.