Showing Compound Card for Vanillin (CDB005772)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-04-27 16:55:03 UTC
Updated at2022-12-13 19:31:28 UTC
CannabisDB IDCDB005772
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameVanillin
DescriptionVanillin, 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 is also classified as a phenolic aldehyde. It is the primary component of the extract of the vanilla bean. Vanillin is most prominent as the principal flavor and aroma compound in vanilla or vanilla extract. Cured vanilla pods contain about 2% by dry weight vanillin. Natural vanilla extract is a mixture of several hundred different compounds in addition to vanillin. Artificial vanilla flavoring is often a solution of pure vanillin, usually of synthetic origin. Synthetic vanillin is made from either guaiacol or from lignin, a constituent of wood which is a byproduct of the paper industry. Synthetic vanillin is now used more often than natural vanilla extract as a flavoring agent in foods, beverages, and pharmaceuticals. Vanillin was first isolated as a relatively pure substance in 1858 by Nicolas-Theodore Gobley, who obtained it by evaporating a vanilla extract to dryness and recrystallizing the resulting solids from hot water. Vanillin has a sweet, chocolate, and creamy aroma and a vanilla, sweet, creamy taste. It is used widely by the food industry. The ice cream and chocolate industries together comprise 75% of the market for vanillin as a flavoring agent, with smaller amounts being used in confections and baked goods. Vanillin is also used in the fragrance industry, in perfumes, and to mask unpleasant odors or tastes in medicines, livestock fodder, and cleaning products. It is also used in the flavor industry, as a very important key note for many different flavors, especially creamy profiles such as cream soda. Vanillin is found naturally in a number of plants and plant foods including vanilla, allspice, beet sugar, benzoin gum, blueberries, bilberries, cloves, coffee, corn, fennel, ginger, grapes, nutmeg, oats, peppermint, pineapple, rum, strawberries, sunflower seeds, and tomatoes. Vanillin has also been detected, but not quantified in pecan nuts, durians, wax apples, welsh onions, and broad beans. Vanillin biosynthesis is generally part of the phenylpropanoid pathway starting with l-phenylalanine, which is deaminated by phenylalanine ammonia lyase (PAL) to form t-cinnamic acid. The para position of the ring is then hydroxylated by the cytochrome P450 enzyme cinnamate 4-hydroxylase (C4H/P450) to create p-coumaric acid.[28] Then, in the proposed ferulate pathway, 4-hydroxycinnamoyl-CoA ligase (4CL) attaches p-coumaric acid to coenzyme A (CoA) to create p-coumaroyl CoA. Hydroxycinnamoyl transferase (HCT) then converts p-coumaroyl CoA to 4-coumaroyl shikimate/quinate. This subsequently undergoes oxidation by the P450 enzyme coumaroyl ester 3’-hydroxylase (C3’H/P450) to give caffeoyl shikimate/quinate. HCT then exchanges the shikimate/quinate for CoA to create caffeoyl CoA, and 4CL removes CoA to afford caffeic acid. Caffeic acid then undergoes methylation by caffeic acid O-methyltransferase (COMT) to give ferulic acid. Finally, vanillin synthase hydratase/lyase (vp/VAN) catalyzes hydration of the double bond in ferulic acid followed by a retro-aldol elimination to afford vanillin. Vanillin is a constituent of cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3-Methoxy-4-hydroxybenzaldehydeChEBI
4-Formyl-2-methoxyphenolChEBI
4-Hydroxy-3-methoxy-benzaldehydeChEBI
4-Hydroxy-3-methoxybenzaldehydeChEBI
4-Hydroxy-m-anisaldehydeChEBI
Methylprotocatechuic aldehydeChEBI
p-Hydroxy-m-methoxybenzaldehydeChEBI
p-VanillinChEBI
VanilineChEBI
VanillaldehydeChEBI
Vanillic aldehydeChEBI
5-BromovanillinMeSH
5-ChlorovanillinMeSH
Vanillin, sodium saltMeSH
2-Methoxy-4-formylphenolHMDB
4-Hydroxy 3-methoxybenzaldehydeHMDB
4-Hydroxy-3-methoxy-benzaldehyde-5-chlorovanillinHMDB
4-Hydroxy-3-methoxybenzaldehyde (acd/name 4.0)HMDB
4-Hydroxy-5-methoxybenzaldehydeHMDB
LioxinHMDB
m-Methoxy-p-hydroxybenzaldehydeHMDB
Methyl-protocatechualdehydeHMDB
Methylprotcatechuic aldehydeHMDB
oleo-Resins vanillaHMDB
oleo-Resins vanilla-beanHMDB
Oleoresin vanillaHMDB
PropenylguaetholHMDB
Protocatechualdehyde 3-methyl etherHMDB
trans-2-Ethoxy-5-(1-propenyl)phenolHMDB
VanilinHMDB
VanillaHMDB
Vanilla oleoresinHMDB
Vanillin (3-methoxy-4-hydroxy- benzaldehyde)HMDB
Vanillin (natural)HMDB
Vanillin (NF)HMDB
Vanillin sodium saltHMDB
VanillineHMDB
ZimcoHMDB
4-Hydroxy-3-methoxy-benzyldehydePhytoBank
VanillumPhytoBank
VanillinHMDB
Chemical FormulaC8H8O3
Average Molecular Weight152.15
Monoisotopic Molecular Weight152.0473
IUPAC Name4-hydroxy-3-methoxybenzaldehyde
Traditional Namevanillin
CAS Registry Number121-33-5
SMILES
COC1=C(O)C=CC(C=O)=C1
InChI Identifier
InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3
InChI KeyMWOOGOJBHIARFG-UHFFFAOYSA-N
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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point81.5 °CNot Available
Boiling Point285 °CWikipedia
Water Solubility11 mg/mL at 25 °CNot Available
logP1.21HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP1.31ALOGPS
logP1.22ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)7.81ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.09 m³·mol⁻¹ChemAxon
Polarizability14.82 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0udi-5900000000-907c9684d5ac0386d5222014-09-20View Spectrum
GC-MSVanillin, non-derivatized, GC-MS Spectrumsplash10-0udi-1900000000-46e0edb3260b8896145eSpectrum
GC-MSVanillin, non-derivatized, GC-MS Spectrumsplash10-0udi-7900000000-ee0a0ad1232fa889e567Spectrum
GC-MSVanillin, non-derivatized, GC-MS Spectrumsplash10-0udi-9800000000-d8f749f48a78e7c9c3bfSpectrum
GC-MSVanillin, non-derivatized, GC-MS Spectrumsplash10-00di-1960000000-b6678c7961ee7df779a1Spectrum
GC-MSVanillin, non-derivatized, GC-MS Spectrumsplash10-0udi-1900000000-46e0edb3260b8896145eSpectrum
GC-MSVanillin, non-derivatized, GC-MS Spectrumsplash10-0udi-7900000000-ee0a0ad1232fa889e567Spectrum
GC-MSVanillin, non-derivatized, GC-MS Spectrumsplash10-0udi-9800000000-d8f749f48a78e7c9c3bfSpectrum
GC-MSVanillin, non-derivatized, GC-MS Spectrumsplash10-00di-1960000000-b6678c7961ee7df779a1Spectrum
Predicted GC-MSVanillin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fk9-1900000000-68ebbe847e88a001f8faSpectrum
Predicted GC-MSVanillin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fr-7950000000-08c9e1cb0dbb3704f8eeSpectrum
Predicted GC-MSVanillin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0udi-0900000000-334e2cf1c60f75229fd12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0uy0-0900200200-4cbd13b45290ded181ee2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udr-0900000000-d67b08f1b4f6e90cd2702017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-9fc5182650ced222b1a12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-052b-9800000000-312c82e1fbcda8abeaf72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-0a4j-9700000000-c0da5ed12872161ea30e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000l-5900000000-8c4d3cd8abfc264729a32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-a9b7f966d85c30f6174c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-d1e812bea83f6f84570d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000f-7900000000-9d9283afc35603b0121c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-146c4b184605c821d8222021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00kf-9500000000-f5a8328127a89c12c19e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-014i-9000000000-44efadd4b0c1fe89c39c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-014i-9100000000-70cac2e87a3ecb4ec8672021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0udr-0900000000-10b0539cab1169d8d8772021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-0900000000-17943fa1f4f19dd4878a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0udr-0900000000-2e50ec52313e18cddbd02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0f79-1900000000-98d502286eb47c703f642021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-052e-9800000000-03597a1112a480b91d5e2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-e949414f752aab5e96062015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-1dcee0be3ba8e1431a7c2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ff9-9400000000-dcd0372357bd9c46926d2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-6cc5e0ed993af0b790e62015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-cf1b6af77251971154f92015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-9500000000-302ce8740fbb7b9295b92015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.0294 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.0281 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.029 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.0279 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.0252 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.0277 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0012308
DrugBank IDNot Available
Phenol Explorer Compound ID724
FoodDB IDFDB000838
KNApSAcK IDC00002683
Chemspider ID13860434
KEGG Compound IDC00755
BioCyc IDVANILLIN
BiGG IDNot Available
Wikipedia LinkVanillin
METLIN IDNot Available
PubChem Compound1183
PDB IDV55
ChEBI ID18346
References
General ReferencesNot Available