Compound Summary

General Compound Information

4-hydroxy-3-methoxybenzaldehyde (vanillin)

Description
Vanillin is a member of the class of benzaldehydes carrying methoxy and hydroxy substituents at positions 3 and 4 respectively. It has a role as a plant metabolite, a flavouring agent, an antioxidant and an anticonvulsant. It is a member of phenols, a monomethoxybenzene and a member of benzaldehydes.
Synonyms
vanillin;  4-Hydroxy-3-methoxybenzaldehyde;  121-33-5;  Vanillaldehyde;  Vanillic aldehyde;
FlavorDB ID
2861
PUBCHEM ID
Molecular Weight
152.15
Molecular Formula
C8H8O3
Openeye Can Smiles
COC1=C(C=CC(=C1)C=O)O
IUPAC Inchikey
MWOOGOJBHIARFG-UHFFFAOYSA-N
Compound Classification
  • ClassyFire Ontology
Compound Quality
CATEGORY QUALITY THRESHOLD OCCURENCE REFERENCE
taste astringent 8.290e+2 µmol/L red wine details
taste astringent 3.352e+1 µmol/L whisky details
taste astringent 8.281e+2 µmol/L whisky details
taste astringent 8.290e+2 µmol/L details
taste astringent 8.290e+2 µmol/L red wine details
smell vanilla-like 5.577e-6 µmol/L coffee details
smell 5.915e-6 µmol/L details
smell vanilla-like 5.577e-6 µmol/L grapefruit juice details
smell 5.577e-6 µmol/L orange juice details
smell vanilla-like 5.577e-6 µmol/L wine details
smell vanilla-like, sweet 3.483e-1 µmol/L details
smell vanilla-like, sweet 1.380e+0 µmol/L details
smell vanilla-like 3.483e-1 µmol/L passion fruit details
smell vanilla-like 3.483e-1 µmol/L white alba truffleburgundy truffle details
smell vanilla-like 3.483e-1 µmol/L tomato details
smell 3.483e-1 µmol/L blanched prawnfried prawn details
smell vanilla-like 3.483e-1 µmol/L licorice details
smell vanilla-like 3.483e-1 µmol/L orange juice details
smell 4.400e+2 µg/kg gluten-free rice breadwheat bread details
smell vanilla-like 3.483e-1 µmol/L jackfruit pulp details
smell vanilla-like 3.483e-1 µmol/L cempedak details
smell vanilla-like 3.483e-1 µmol/L barley tea details
smell vanilla-like 3.483e-1 µmol/L green tea details
Compound Toxicity and Food Additive Safety (OFAS)
Toxicity Summary
Link to the Distributed Structure-Searchable Toxicity (DSSTox) Database
IDENTIFICATION: Small quantities of vanillin are used in perfumery to round and fix sweet, balsamic fragrances. Vanillin is also used as a brightener in galvanotechnical processes and is an important intermediate in, for example, the production of pharmaceuticals such as l-3,4-dihydroxyphenylalanine (l-DOPA) and methyldopa. For vanillin (USEPA/OPP Pesticide Code: 115801) there are 0 labels match. /Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./ Pharmaceutic aid (flavor). As a flavoring agent in confectionery, beverages, foods and animal feeds. Fragrance and flavor in cosmetics. Reagent for synthesis.
HUMAN EXPOSURE AND TOXICITY: In closed-patch tests on human skin vanillin caused no primary irritation when tested at concentrations of 20% on 29 normal subjects, at 2% on 30 normal subjects, and at 0.4% on 35 subjects with dermatoses. Maximization tests were conducted on groups of 25 volunteers. The material was tested at concentrations of 2 and 5% in petrolatum and produced no sensitization reactions. Vanillin was considered to be a secondary allergen because sensitivity was found only in patients sensitive to vanilla, isoeugenol, and coniferyl benzoate. Drug interaction between vanillin/ethyl vanillin and drugs metabolized by CYP2E1/CYP1A2 might be possible.
ANIMAL STUDIES: Vanillin injected intraperitoneally into strain A mice in total doses of 3.6-18.0 g/kg over a period of 24 weeks produced no excesses of lung tumors and was not considered to be carcinogenic. Groups of 16 rats were fed diets containing vanillin at levels to provide 20 mg/kg body weight/day for 18 week without any adverse effects, but 64 mg/kg/day for 10 week caused growth depression and damage to myocardium, liver, kidney, lung, spleen, and stomach. In experiments with yeast, vanillin acted as a co-mutagen. The modifying effects of vanillin on the cytotoxicity and 6-thioguanine (6TG)-resistant mutations induced by two different types of chemical mutagens, ethyl methanesulfonate (EMS) and hydrogen peroxide (H2O2), were examined using cultured Chinese hamster V79 cells. The effects of vanillin on H2O2-induced chromosome aberrations were also examined. Vanillin had a dose-dependent enhancing effect on EMS-induced cytotoxicity and 6TG-resistant mutations, when cells were simultaneously treated with vanillin. The post-treatment with vanillin during the mutation expression time of cells after treatment with EMS also showed an enhancement of the frequency of mutations induced by EMS. However, vanillin suppressed the cytotoxicity induced by H2O2 when cells were post-treated with vanillin after H2O2 treatment. Vanillin showed no change in the absence of activity of H2O2 to induce mutations. Post-treatment with vanillin also suppressed the chromosome aberrations induced by H2O2. The differential effects of vanillin were probably due to the quality of mutagen-induced DNA lesions and vanillin might influence at least two different kinds of cellular repair functions. Vanillin (200 ug/culture) was found to directly suppress the in vitro anti-sheep RBC antibody response at noncytotoxic doses.
Source: DrugBank or Hazardous Substances Data Bank (HSDB)
Food Additive Safety (OFAS)
VANILLIN is used for COLOR OR COLORING ADJUNCT, FLAVORING AGENT OR ADJUVANT. More food additive safty information please view GRAS report.
EFSA's chemical Hazards Database : OpenFoodTox
This compound is found in OpenFoodTox with the name: Vanillin
Receptors
Receptor REFERENCE EC50 [µM] Effective Concentration [µM]
OR10G3 details Activated
OR10G4 details Activated
OR1G1 details Activated
OR1L3 details Activated
OR2G2 details Activated
OR2J3 details Activated
OR2M4 details Activated
OR2T10 details Activated
OR2T34 details Activated
OR5AC2 details Activated
Consensus Spectra
Spectrum Type Spectrum View Description Polarity
Experimental GCMS view GCMS positive
Experimental LCMS view LCMS_Positive positive
Experimental LCMS view LCMS_Negative negative