ortho-vanillin
benzaldehyde, 2-hydroxy-3-methoxy-
Identification
| Name | ortho-vanillin |
| CAS Number | 148-53-8 |
| EINECS | 205-715-3 |
| FDA UNII | 008LR748FI |
| Molecular Formula | C8 H8 O3 |
| Molecular Weight | 152.14936000 |
| MDL Number | MFCD00003322 |
| Nikkaji Number | J45.622E |
| Beilstein | 0471913 |
| XlogP3 | 1.40 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 44.00 to 45.00 °C. @ 760.00 mm Hg |
| Boiling Point | 265.00 to 266.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.006000 mmHg @ 25.00 °C. (est) |
| Flash Point | 201.00 °F. TCC ( 94.00 °C. ) (est) |
| logP (o/w) | 1.370 |
| Soluble in | alcohol |
| Insoluble in | water |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | intraperitoneal-rat LD50 347 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for ortho-vanillin usage levels up to | not for fragrance use. |
| Recommendation for ortho-vanillin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
benzaldehyde, 2-hydroxy-3-methoxy-
6-
formyl guaiacol
6-
formyl-2-methoxyphenol
6-
formylguaiacol
2-
hydroxy-3-(methyloxy)benzaldehyde
2-
hydroxy-3-methoxy-benzaldehyde
2-
hydroxy-3-methoxybenzaldehyde
2-
hydroxy-m-anisaldehyde
2-
hydroxy-meta-anisaldehyde
3-
methoxysalicylaldehyde
o-
vanilin
2-
vanillin
o-
vanillin
PubMed:
Slow magnetic relaxation of light lanthanide-based linear LnZn2 trinuclear complexes.
PubMed:
Structural switching from paramagnetic to single-molecule magnet behaviour of LnZn2 trinuclear complexes.
PubMed:
Investigation of the salicylaldehyde thiosemicarbazone scaffold for inhibition of influenza virus PA endonuclease.
PubMed:
The exceptionally rich coordination chemistry generated by Schiff-base ligands derived from o-vanillin.
PubMed:
Crystal Structure, Cytotoxicity and Interaction with DNA of Zinc (II) Complexes with o-Vanillin Schiff Base Ligands.
PubMed:
Optimization of Purification, Identification and Evaluation of the in Vitro Antitumor Activity of Polyphenols from Pinus Koraiensis Pinecones.
PubMed:
A versatile salicyl hydrazonic ligand and its metal complexes as antiviral agents.
PubMed:
Total Synthesis and Antimicrobial Activity of Chlorocatechelin A.
PubMed:
Inhibition of TLR2 signaling by small molecule inhibitors targeting a pocket within the TLR2 TIR domain.
PubMed:
Anti-proliferative effect of Fe(III) complexed with 1-(2-hydroxy-3-methoxybenzaldehyde)-4-aminosalicylhydrazone in HepG2 cells.
PubMed:
Homodinuclear lanthanide {Ln2} (Ln = Gd, Tb, Dy, Eu) complexes prepared from an o-vanillin based ligand: luminescence and single-molecule magnetism behavior.
PubMed:
Synthesis of three rimantadine schiff bases and their biological effects on serum albumin.
PubMed:
A magnetically highly frustrated Cu(II)27 coordination cluster containing a Cu18 folded-sheet motif.
PubMed:
Structural, spectroscopic and DFT study of 4-methoxybenzohydrazide Schiff bases. A new series of polyfunctional ligands.
PubMed:
Single-chain magnetic behavior in a hetero-tri-spin complex mediated by supramolecular interactions with TCNQFËâ» radicals.
PubMed:
First total synthesis of antihypertensive natural products S-(+)-XJP and R-(-)-XJP.
PubMed:
Magnetic and luminescent binuclear double-stranded helicates.
PubMed:
A chiral, low-cytotoxic [Ni15]-wheel complex.
PubMed:
Synthesis, spectral characterization, DNA binding studies and antimicrobial activity of Co(II), Ni(II), Zn(II), Fe(III) and VO(IV) complexes with 4-aminoantipyrine Schiff base of ortho-vanillin.
PubMed:
New ruthenium(II) carbonyl complexes bearing disulfide Schiff base ligands and their applications as catalyst for some organic transformations.
PubMed:
Synthesis, crystal structure, fluorescence and electrochemical studies of a new tridentate Schiff base ligand and its nickel(II) and palladium(II) complexes.
PubMed:
A dinuclear cadmium(II) Schiff base thiocyanato complex: crystal structure and fluorescence.
PubMed:
Self-assembly of a 15-nickel metallamacrocyclic complex derived from the L-glutamic acid Schiff base ligand.
PubMed:
Laccase catalyzed synthesis of iodinated phenolic compounds with antifungal activity.
PubMed:
Effects of o-vanillin on K⺠transport of red blood cells from patients with sickle cell disease.
PubMed:
A vanillin derivative causes mitochondrial dysfunction and triggers oxidative stress in Cryptococcus neoformans.
PubMed:
Spectral, electrochemical, thermal, DNA binding ability, antioxidant and antibacterial studies of novel Ru(III) Schiff base complexes.
PubMed:
Synthesis, structural characterization, and magnetic properties of a copper-gadolinium complex derived from a hydroxybenzohydrazide ligand.
PubMed:
Enantioselective total synthesis of dysidavarone A, a novel sesquiterpenoid quinone from the marine sponge Dysidea avara.
PubMed:
Spectral and molecular modeling studies on hydroxybenzaldehydes with native and modified cyclodextrins.
PubMed:
Conjugation of benzylvanillin and benzimidazole structure improves DNA binding with enhanced antileukemic properties.
PubMed:
A new quaternary photoluminescence enhancement system of Eu-N-(o-vanillin)-1,8-diaminonaphthalene-1,10-phenanthroline-Zn and its application in determining trace amounts of europium and zinc.
PubMed:
Solvent-free Mechanosynthesis of Two Thermochromic Schiff Bases.
PubMed:
An experimental and DFT study of a disulfide-linked Schiff base: synthesis, characterization and crystal structure of bis (3-methoxy-salicylidene-2-aminophenyl) disulfide in its anhydrous and monohydrate forms.
PubMed:
Spectroscopic, thermal analysis and DFT computational studies of salen-type Schiff base complexes.
PubMed:
Butterfly-shaped pentanuclear dysprosium single-molecule magnets.
PubMed:
Ferrocene-based compartmental ligand for the assembly of neutral Zn(II)/Ln(III) heterometallic complexes.
PubMed:
NIR luminescence and catalysis of multifarious salen type ytterbium complexes modulated by anions.
PubMed:
New nickel(II) and copper(II) complexes with unsymmetrical Schiff bases derived from (1R,2R)(-)cyclohexanediamine and the application of Cu(II) complexes for hybrid thin layers deposition.
PubMed:
Biological activities and chemical composition of the stems and roots of Helichrysum oligocephalum DC grown in Iran.
PubMed:
Organic cadmium complexes as proteasome inhibitors and apoptosis inducers in human breast cancer cells.
PubMed:
Synthesis, crystal structure and interaction of L-valine Schiff base divanadium(V) complex containing a V2O3 core with DNA and BSA.
PubMed:
Cu(II)-azide polynuclear complexes of Cu4 building clusters with Schiff-base co-ligands: synthesis, structures, magnetic behavior and DFT studies.
PubMed:
A non-electrolyte haemolysis assay for diagnosis and prognosis of sickle cell disease.
PubMed:
Synthesis and biological evaluation of noscapine analogues as microtubule-interfering agents.
PubMed:
Self-assembly of [Cu(II)Tb(III)]3+ and [W(CN)8]3- tectons: a case study of a mixture containing two complexes showing slow-relaxation of the magnetization.
PubMed:
2-Hy-droxy-3-meth-oxy-benzaldehyde (o-vanillin) revisited.
PubMed:
Correlation between slow magnetic relaxation and the coordination structures of a family of linear trinuclear Zn(II)-Ln(III)-Zn(II) complexes (Ln = Tb, Dy, Ho, Er, Tm and Yb).
PubMed:
One- and two-photon induced emission in heterobimetallic Zn(II)-Sm(III) and Zn(II)-Tb(III) complexes with a side-off compartmental ligand.
PubMed:
Polydentate-ligand-supported self-assembly of heterometallic T-shaped Co4RE (RE = Gd, Tb, Y) clusters: synthesis, structure and magnetism.
PubMed:
Bis[μ-N-(3-meth-oxy-2-oxidobenzyl-idene-1:2κ(2)O(2):O(2))-l-isoleucinato-2κ(2)N,O]bis-(1,10-phenanthroline-1κ(2)N,N')dinickel(II) methanol tetra-solvate trihydrate.
PubMed:
Molecular assembly and magnetic dynamics of two novel Dy6 and Dy8 aggregates.
PubMed:
The conductance of red blood cells from sickle cell patients: ion selectivity and inhibitors.
PubMed:
Cyclo- and carbophosphazene-supported ligands for the assembly of heterometallic (Cu2+/Ca2+, Cu2+/Dy3+, Cu2+/Tb3+) complexes: synthesis, structure, and magnetism.
PubMed:
Development of a fluorescent chelating ligand for scandium ion having a Schiff base moiety.
PubMed:
Food protective effects of Periploca sepium oil and its active component against stored food mites.
PubMed:
Heterometallic cubane-like {M2Ln2} (M = Ni, Zn; Ln =, Gd, Dy) and {Ni2Y2} aggregates. Synthesis, structures and magnetic properties.
PubMed:
New 1,2,4-triazole-based azo-azomethine dyes. Part I: synthesis, characterization and spectroscopic studies.
PubMed:
Defect-dicubane Ni2Ln2 (Ln = Dy, Tb) single molecule magnets.
PubMed:
Magnetic anisotropy in Ni(II)-Y(III) binuclear complexes: on the importance of both the first coordination sphere of the Ni(II) ion and the Y(III) ion belonging to the second coordination sphere.
PubMed:
Spectroscopic analyses on interaction of Amantadine-Salicylaldehyde, Amantadine-5-Chloro-Salicylaldehyde and Amantadine-o-Vanillin Schiff-Bases with bovine serum albumin (BSA).
PubMed:
Modulating magnetic dynamics of three Dy2 complexes through keto-enol tautomerism of the o-vanillin picolinoylhydrazone ligand.
PubMed:
Approaching polymetallic 'assemblies of assemblies' using ligands with multiple functionality--novel Mn10M2 (M = alkali metal) chains with 'ionophoric' end cavities.
PubMed:
[N-(3-Meth-oxy-2-oxidobenzyl-idene-κO)threoninato-κO,N](1,10-phenanthroline-κN,N')copper(II) hemihydrate.
PubMed:
6-Meth-oxy-2-[(E)-phenyl-imino-meth-yl]phenol.
PubMed:
Study of the luminescent and magnetic properties of a series of heterodinuclear [Zn(II)Ln(III)] complexes.
PubMed:
Preparation, crystal structures, and magnetic features for a series of dinuclear [Ni(II)Ln(III)] Schiff-base complexes: evidence for slow relaxation of the magnetization for the Dy(III) derivative.
PubMed:
Kojic acid derivatives as powerful chelators for iron(III) and aluminium(III).
PubMed:
Syntheses, spectral, electrochemical and thermal studies of mononuclear manganese(III) complexes with ligands derived from 1,2-propanediamine and 2-hydroxy-3 or 5-methoxybenzaldehyde: self-assembled monolayer formation on nanostructure zinc oxide thin film.
PubMed:
1,2-Bis(2-meth-oxy-6-formyl-phen-oxy)ethane.
PubMed:
Dimers and chains of {3d-4f} single molecule magnets constructed from heterobimetallic tectons.
PubMed:
[Simultaneous separation and determination of vanillin and o-vanillin by capillary zone electrophoresis].
PubMed:
Spectroscopic analyses on interaction of o-Vanillin-D-Phenylalanine, o-Vanillin-L-Tyrosine and o-Vanillin-L-Levodopa Schiff Bases with bovine serum albumin (BSA).
PubMed:
Vanadium polypyridyl compounds as potential antiparasitic and antitumoral agents: new achievements.
PubMed:
Synthesis, characterization and biocidal activities of some schiff base metal complexes.
PubMed:
Chiral transition metal clusters from two enantiomeric schiff base ligands. Synthesis, structures, CD spectra and magnetic properties.
PubMed:
2-Hydroxy-3-methoxybenzaldehyde 2,4-dinitrophenylhydrazone pyridine monosolvate.
PubMed:
Theoretical study of structure and electronic absorption spectra of some Schiff bases and their zinc complexes.
PubMed:
Spectroscopic study and structure of (E)-2-[(2-chlorobenzylimino)methyl]methoxyphenol.
PubMed:
Synthesis and characterisation of thiosemicarbazonato molybdenum(VI) complexes and their in vitro antitumor activity.
PubMed:
A heterobimetallic Ga/Yb-Schiff base complex for catalytic asymmetric alpha-addition of isocyanides to aldehydes.
PubMed:
Synthesis, characterization, crystal structure and antibacterial activities of transition metal(II) complexes of the schiff base 2-[(4-methylphenylimino)methyl]-6-methoxyphenol.
PubMed:
4-Amino-5-(2-hydroxy-benzyl-idene-amino)benzene-1,2-dicarbonitrile.
PubMed:
Bis[2-(benzyl-amino)pyridine-κN](2-formyl-6-methoxy-phenolato-κO,O)(nitrato-κO,O')nickel(II).
PubMed:
2-Meth-oxy-6-[(Z)-[(5-methyl-2-pyrid-yl)imino-meth-yl]phenol.
PubMed:
Mononuclear Ru(III) Schiff base complexes: synthesis, spectral, redox, catalytic and biological activity studies.
PubMed:
Anion-perturbed magnetic slow relaxation in planar {Dy4} clusters.
PubMed:
Synthesis and characterization of a novel cross-linking complex of beta-cyclodextrin-o-vanillin furfuralhydrazone and highly selective spectrofluorimetric determination of trace gallium.
PubMed:
Rapid and sensitive spectrofluorimetric determination of trace amount of Cr(III) with o-vanillin-8-aminoquinoline.
PubMed:
Determination of trace osmium by supramolecular catalytic kinetic spectrofluorimetry of beta-CD-osmium-KBrO(3)-o-vanillin furfuralhydrazone.
PubMed:
Separation and preconcentration of metal ions and their estimation in vitamin, steel and milk samples using o-vanillin-immobilized silica gel.
PubMed:
Spectrometric study of tautomeric and protonation equilibria of o-vanillin Schiff base derivatives and their complexes with Cu(II).
PubMed:
(E)-N'-[2-(4-Chloro-3-nitro-phenyl-sulfon-yloxy)-3-methoxy-benzyl-idene]isonicotinohydrazide acetic acid tetra-solvate.
PubMed:
A four-armed Schiff base: 6,6',6'',6'''-tetra-meth-oxy-2,2',2'',2'''-[methanetetra-yltetra-kis(methylenenitrilo-methyl-idyne)]tetra-phenol.
PubMed:
(2-Formyl-6-methoxy-phenolato-κO,O)(perchlorato-κO)(1,10-phenanthroline-κN,N')copper(II).
PubMed:
Effect of natural phenol derivatives on skeletal type sarcoplasmic reticulum Ca2+ -ATPase and ryanodine receptor.
PubMed:
Re-evaluation of cyclooxygenase-2-inhibiting activity of vanillin and guaiacol in macrophages stimulated with lipopolysaccharide.
PubMed:
Interaction of vanadyl (VO2+) with ligands containing serine, tyrosine, and threonine.
PubMed:
Ligating properties of a potentially tetradentate Schiff base [(CH3)2NCH2CH2N=CHC6H3(OH)(OMe)] with zinc(II), cadmium(II), cobalt(II), cobalt(III) and manganese(III) ions: synthesis and structural studies.
PubMed:
Method for determining the average degree of substitution of o-vanillin derivatized porcine somatotropin.
PubMed:
Flow injection kinetic spectrofluorimetric determination of trace amounts of osmium.
PubMed:
Synthesis, characterization, redox property and biological activity of Ru(II) carbonyl complexes containing O,N-donor ligands and heterocyclic bases.
PubMed:
Synthesis of a novel host molecule of cross-linking-polymeric-beta-cyclodextrin-o-vanillin furfuralhydrazone and spectrofluorimetric analysis of its identifying cadmium.
PubMed:
Crystal structure and magnetic interactions in nickel(II) dibridged complexes formed by two azide groups or by both phenolate oxygen-azide, -thiocyanate, -carboxylate, or -cyanate groups.
PubMed:
Antibacterial activities of phenolic benzaldehydes and benzoic acids against Campylobacter jejuni, Escherichia coli, Listeria monocytogenes, and Salmonella enterica.
PubMed:
Structure-based description of a step-by-step synthesis of homo- and heterodinuclear (4f, 4f ') lanthanide complexes.
PubMed:
Synthesis and characterization of a novel cross-linking complex of beta-cyclodextrin-o-vanillin benzoylhydrazone and its selective spectrofluorimetric determination of trace amounts of zinc.
PubMed:
A novel potato defence-related alcohol:NADP+ oxidoreductase induced in response to Erwinia carotovora.
PubMed:
Total synthesis of ailanthoidol and precursor XH14 by Stille coupling.
PubMed:
Vibrational analysis of substituted phenols: part I. Vibrational spectra, normal coordinate analysis and transferability of force constants of some formyl-, methoxy-, formylmethoxy-, methyl- and halogeno-phenols.
PubMed:
Chemical analysis and antifungal activity of the essential oil of Calea clematidea.
PubMed:
Selective targeting of synthetic antioxidants to mitochondria: towards a mitochondrial medicine for neurodegenerative diseases?
PubMed:
Free radical scavenging activity of vanillin and o-vanillin using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical.
PubMed:
Syntheses, X-ray crystal structures, and magnetic properties of novel linear M2[II]U[IV] complexes (M=Co, Ni, Cu, Zn).
PubMed:
Dissolution behavior of porcine somatotropin with simultaneous gel formation and lysine Schiff-base hydrolysis.
PubMed:
Influence of anionic ligands (X) on the nature and magnetic properties of dinuclear LCuDgX3.nH2O complexes (LH2 standing for tetradentate Schiff base ligands deriving from 2-hydroxy-3-methoxybenzaldehyde and X being Cl, N3C2, and CF3COO).
PubMed:
Oxovanadium(IV) complexes with aromatic aldehydes.
PubMed:
Validation of single cell gel assay in human leukocytes with 18 reference compounds.
PubMed:
Synthesis of (+/-)-cassumunins A and B, new curcuminoid antioxidants having protective activity of the living cell against oxidative damage.
PubMed:
Synthesis and biological activity of platinum group metal complexes of o-vanillin thiosemicarbazones.
PubMed:
Bidirectional transformation of aromatic aldehydes by Desulfovibrio desulfuricans under nitrate-dissimilating conditions.
PubMed:
Studies on the antitumor 2,6-piperazinediones: synthesis of 2,3-diacetoxy-4-carbomethoxy-(3',5'-dioxo-N4' substituted piperazinyl methyl) benzene.
PubMed:
Mutation enhancing effect of o-vanillin in the lacZ gene of Escherichia coli: characterization of mutational spectrum.
PubMed:
[Studies on uranium mobilization agents VI: synthesis of 2,3-dihydroxy-4-carbomethoxybenzyl aminocarboxylic acid amides chelating agents].
PubMed:
o-Vanillin enhances chromosome aberrations induced by alkylating agents in cultured Chinese hamster cells.
PubMed:
Oxidation of benzaldehydes to benzoic acid derivatives by three Desulfovibrio strains.
PubMed:
Synthesis of 4- and 16 alpha-hydroxylated equine estrogens.
PubMed:
Effects of vanillin and o-vanillin on induction of DNA-repair networks: modulation of mutagenesis in Escherichia coli.
PubMed:
Inhibition of induction of adaptive response by o-vanillin in Escherichia coli B.
PubMed:
Enhancement and inhibition of mutation by o-vanillin in Escherichia coli.
PubMed:
A specific inhibition of induction of adaptive response by o-vanillin, a potent comutagen.
PubMed:
Studies on antifungal agents: aromatic acid hydrazones of o. vanillin, o. veratraldehyde, 5-bromo-o. vanillin and bourbonal.
PubMed:
Schiff base adducts of hemoglobin. Modifications that inhibit erythrocyte sickling.
PubMed:
[On the preparation of 5-iodo-o-vanillin and the preparation of Beta-nitrostyrols. On the knowledge of o-vanillin, VII].
PubMed:
[Benzoins, benzils and benzilic acids of o-vanillin- and o-novovanillin ether].
PubMed:
[DERIVATIVES OF 2-HYDROXY-3-METHOXYBENZALDEHYDE].
PubMed:
[On the knowledge of o-vanillin. Part VI. Keto bases of pyrocatechol].
PubMed:
[Data on o-vanillin & novovanillin (2-hydroxy-3-ethoxybenzaldehyde). II. Preparation of 2,3-dialkoxyphenyl-beta-ethylamine].
PubMed:
[Research on benzopyrones; coumarin derivatives of o-vanillin].
PubMed:
[Toxicity of vanillin, o-vanillin, ethylvanillin and the corresponding isophthalaldehydes].
PubMed:
Coumarins from 2-hydroxy-3-methoxybenzaldehyde.