Basic Info

Common NameVanillin(F05551)
2D Structure
Description

Vanillin is the primary component of the extract of the vanilla bean. Synthetic vanillin, instead of natural vanilla extract, is sometimes used as a flavouring agent in foods, beverages, and pharmaceuticals. It is used by the food industry as well as ethylvanillin.Artificial vanilla flavoring is a solution of pure vanillin, usually of synthetic origin. Because of the scarcity and expense of natural vanilla extract, there has long been interest in the synthetic preparation of its predominant component. The first commercial synthesis of vanillin began with the more readily available natural compound eugenol. Today, artificial vanillin is made from either guaiacol or from lignin, a constituent of wood which is a byproduct of the paper industry. (Wiki).

FRCD IDF05551
CAS Number121-33-5
PubChem CID1183
FormulaC8H8O3
IUPAC Name

4-hydroxy-3-methoxybenzaldehyde

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

Canonical SMILES

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

Isomeric SMILES

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

WikipediaVanillin
Synonyms
        
            4-Hydroxy-3-methoxybenzaldehyde
        
            vanillin
        
            121-33-5
        
            Vanillaldehyde
        
            Vanillic aldehyde
        
            Vanilla
        
            p-Vanillin
        
            2-Methoxy-4-formylphenol
        
            Vanilline
        
            Lioxin
        
Classifies
                

                  
                    Predicted: Veterinary Drug
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassPhenols
SubclassMethoxyphenols
Intermediate Tree NodesNot available
Direct ParentMethoxyphenols
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsMethoxyphenol - 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
DescriptionThis compound belongs to the class of organic compounds known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Properties

Property NameProperty Value
Molecular Weight152.149
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count2
Complexity135
Monoisotopic Mass152.047
Exact Mass152.047
XLogP1.2
Formal Charge0
Heavy Atom Count11
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.7465
Human Intestinal AbsorptionHIA+0.9954
Caco-2 PermeabilityCaco2+0.9065
P-glycoprotein SubstrateNon-substrate0.6592
P-glycoprotein InhibitorNon-inhibitor0.8476
Non-inhibitor0.8664
Renal Organic Cation TransporterNon-inhibitor0.8820
Distribution
Subcellular localizationMitochondria0.9328
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7444
CYP450 2D6 SubstrateNon-substrate0.8552
CYP450 3A4 SubstrateNon-substrate0.6548
CYP450 1A2 InhibitorNon-inhibitor0.7125
CYP450 2C9 InhibitorNon-inhibitor0.9643
CYP450 2D6 InhibitorNon-inhibitor0.9662
CYP450 2C19 InhibitorNon-inhibitor0.7401
CYP450 3A4 InhibitorNon-inhibitor0.9561
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8592
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9664
Non-inhibitor0.9442
AMES ToxicityNon AMES toxic0.9311
CarcinogensNon-carcinogens0.8759
Fish ToxicityHigh FHMT0.7007
Tetrahymena Pyriformis ToxicityHigh TPT0.9242
Honey Bee ToxicityHigh HBT0.7610
BiodegradationReady biodegradable0.7561
Acute Oral ToxicityIII0.8545
Carcinogenicity (Three-class)Non-required0.5099

Model Value Unit
Absorption
Aqueous solubility-1.3461LogS
Caco-2 Permeability1.3620LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.9642LD50, mol/kg
Fish Toxicity1.7984pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.1291pIGC50, ug/L

References

TitleJournalDatePubmed ID
Expression of Gre2p improves tolerance of engineered xylose-fermenting Saccharomyces cerevisiae to glycolaldehyde under xylose metabolism.Appl Microbiol Biotechnol2018 Sep30027490
Toasted vine-shoot chips as enological additive.Food Chem2018 Oct 1529784334
Evaluation of e-liquid toxicity using an open-source high-throughput screening assay.PLoS Biol2018 Mar29584716
Changes in the Key Odorants and Aroma Profiles of Hamlin and Valencia OrangeJuices Not from Concentrate (NFC) during Chilled Storage.J Agric Food Chem2018 Jul 1829889522
Olfactory toxicity in rats following manganese chloride nasal instillation: Apilot study.Neurotoxicology2018 Jan28917718
Vanillin biotechnology: the perspectives and future.J Sci Food Agric2018 Aug 930094833
A colorimetric assay for vanillin detection by determination of the luminescence of o-toluidine condensates.PLoS One2018 Apr 2029677193
Vertical Leaching of Allelochemicals Affecting Their Bioactivity and theMicrobial Community of Soil.J Agric Food Chem2017 Sep 1328800227
Groove Binding of Vanillin and Ethyl Vanillin to Calf Thymus DNA.J Fluoresc2017 Sep28547116
Effects of organic acids and essential oils blend on growth, gut microbiota,immune response and disease resistance of Pacific white shrimp (Litopenaeusvannamei) against Vibrio parahaemolyticus.Fish Shellfish Immunol2017 Nov28882791
Homodimers of Vanillin and Apocynin Decrease the Metastatic Potential of HumanCancer Cells by Inhibiting the FAK/PI3K/Akt Signaling Pathway.J Agric Food Chem2017 Mar 2228248106
Simple synthesis of cobalt sulfide nanorods for efficient electrocatalyticoxidation of vanillin in food samples.J Colloid Interface Sci2017 Mar 1527951514
Low-dose acute vanillin is beneficial against harmaline-induced tremors in rats.Neurol Res2017 Mar28095756
Facile Synthesis of Novel Vanillin Derivatives Incorporating aBis(2-hydroxyethyl)dithhioacetal Moiety as Antiviral Agents.J Agric Food Chem2017 Jun 1428545296
Porous calcium carbonate as a carrier material to increase the dissolution rateof poorly soluble flavouring compounds.Food Funct2017 Apr 1928295108
Impact of preharvest and postharvest alginate treatments enriched with vanillinon postharvest decay, biochemical properties, quality and sensory attributes oftable grapes.Food Chem2017 Apr 1527979175
Aldehyde Oxidase 4 Plays a Critical Role in Delaying Silique Senescence by Catalyzing Aldehyde Detoxification.Plant Physiol2017 Apr28188272
Conditions Optimizing and Application of Laccase-mediator System (LMS) for theLaccase-catalyzed Pesticide Degradation.Sci Rep2016 Oct 2427775052
Airway epithelial cell exposure to distinct e-cigarette liquid flavorings revealstoxicity thresholds and activation of CFTR by the chocolate flavoring2,5-dimethypyrazine.Respir Res2016 May 1727184162
Assessment of Angelica sinensis (Oliv.) Diels as a repellent for personalprotection against mosquitoes under laboratory and field conditions in northernThailand.Parasit Vectors2016 Jun 2927357395

Targets

General Function:
Zinc ion binding
Specific Function:
Can degrade fibronectin, laminin, gelatins of type I, III, IV, and V; collagens III, IV, X, and IX, and cartilage proteoglycans. Activates procollagenase.
Gene Name:
MMP3
Uniprot ID:
P08254
Molecular Weight:
53976.84 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]