2169-99-5

Basic information

• Product Name: o-Vanillin oxime
• Synonyms: o-Vanillin oxime;2-[(1E)-(hydroxyimino)methyl]-6-methoxyphenol;(6z)-6-[(hydroxyamino)methylidene]-2-methoxycyclohexa-2,4-dien-1-one
• CAS NO: 2169-99-5
• Molecular Formula: C₈H₉NO₃
• Molecular Weight: 167.163
• Mol File: 2169-99-5.mol

Chemical Properties

• Melting Point: 124 °C
• Boiling Point: 345.3°Cat760mmHg
• Flash Point: 162.6°C
• Appearance: /
• Density: 1.27g/cm³
• Vapor Pressure: 3.93E-06mmHg at 25°C
• Refractive Index: 1.577
• PKA: 9.11±0.40(Predicted)
• CAS DataBase Reference: o-Vanillin oxime(CAS DataBase Reference)
• NIST Chemistry Reference: o-Vanillin oxime(2169-99-5)
• EPA Substance Registry System: o-Vanillin oxime(2169-99-5)

Safety Data

• Hazardous Substances Data: 2169-99-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
o-Vanillin oxime is used as a key intermediate in organic synthesis for the production of various chemical compounds due to its reactive oxime group, which facilitates the formation of a wide range of derivatives.
Used in the Food Industry:
o-Vanillin oxime is used as a flavorant to enhance the taste and aroma of food products, capitalizing on its ability to mimic natural vanilla flavors and contribute to the overall sensory experience of the food.
Used in Pharmaceutical Production:
o-Vanillin oxime is utilized as a starting material for the synthesis of pharmaceuticals, leveraging its unique chemical properties to create active ingredients or intermediates in drug development.
Used in Perfumery:
o-Vanillin oxime is employed as a component in the creation of perfumes and other aromatic compounds, where its ability to form derivatives contributes to the complexity and richness of fragrances.
Used in Materials Science:
o-Vanillin oxime is used in the development of new polymers and materials with specific properties, such as improved stability or reactivity, by incorporating its unique chemical structure into the material composition.
Used in Antimicrobial Applications:
o-Vanillin oxime is studied for its potential antimicrobial properties, which could be harnessed in various applications, such as preservatives in food or as components in antimicrobial coatings and materials.
Used in Antioxidant Applications:
o-Vanillin oxime is explored for its antioxidant capabilities, which may find use in various industries, including food preservation, cosmetics, and pharmaceuticals, to protect against oxidative damage and extend shelf life or enhance health benefits.

InChI:InChI=1/C8H9NO3/c1-12-7-4-2-3-6(5-9-11)8(7)10/h2-5,9,11H,1H3/b6-5+

Upstream product

• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 

Downstream Products

• 6812-16-4 2-Hydroxy-3-methoxybenzonitrile 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 88791-24-6 2-mercapto-3-methoxybenzonitrile 
• 88791-27-9 3-amino-7-methoxy-1,2-benzisothiazole 
• 88791-22-4 O-(2-cyano-6-methoxyphenyl)-NN-dimethylthiocarbamate 
• 88791-23-5 S-(2-cyano-6-methoxyphenyl)-NN-dimethylthiocarbamate 
• 2555-20-6 8-methoxy-2-oxo-2H-chromene-3-carboxylic acid 
• 78094-43-6 1-(2-hydroxy-3-methoxyphenyl)propan-1-one 
• 86855-27-8 2-(aminomethyl)-6-methoxyphenol 
• 357922-23-7 [TiCl₃(CH₃OC₆H₃(OH)CHNO)] 
• 357922-24-8 [TiCl₂(CH₃OC₆H₃(OH)CHNO)2] 
• 357922-25-9 [TiCl(CH₃OC₆H₃(OH)CHNO)3] 

Relevant articles and documents

Nine members of a family of nine-membered cyclic coordination clusters; Fe6Ln3 wheels (Ln = Gd to Lu and Y)

We report a family of isostructural nonanuclear FeIII-LnIII cyclic coordination clusters [FeIII6LnIII3(μ-OMe)9(vanox)6(benz)6]. (Ln = Tb (1), Dy (2), Ho (3), Er (4), Tm (5), Yb (6), Lu (7), Y (8) and

Opening up a dysprosium triangle by ligand oximation

A simple trinuclear dysprosium complex shows complex slow relaxation of the magnetisation.

A {Co9IICo3III} dodecanuclear cluster based on o-vanillin oxime: Synthesis, structures and properties

A new dodecanuclear cluster [Co9IICo3III(MeOsalox)6(OAc)15(H2O)6]·2MeCN·2H2O (1) (H2MeOsalox = 3-methyloxysalicylaldoxime) was synthesized under

Synthesis and SAR study of simple aryl oximes and nitrofuranyl derivatives with potent activity against Mycobacterium tuberculosis

Background: Oximes and nitrofuranyl derivatives are particularly important compounds in medicinal chemistry. Thus, many researchers have been reported to possess antibacterial, antiparasitic, insecticidal and fungicidal activities. Methods: In this work, we report the synthesis and the biological activity against Mycobacterium tuberculosis H37RV of a series of fifty aryl oximes, ArCH=N-OH, I, and eight nitrofuranyl compounds, 2-nitrofuranyl-X, II. Results: Among the oximes, I: Ar = 2-OH-4-OH, 42, and I: Ar = 5-nitrofuranyl, 46, possessed the best activity at 3.74 and 32.0 μM, respectively. Also, 46, the nitrofuran compounds, II; X = MeO, 55, and II: X = NHCH2Ph, 58, (14.6 and 12.6 μM, respectively), exhibited excellent biological activities and were non-cytotoxic. Conclusion: The compound 55 showed a selectivity index of 9.85. Further antibacterial tests were performed with compound 55 which was inactive against Enterococcus faecalis, Klebisiella pneumonae, Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhymurium and Shigel-la flexneri. This study adds important information to the rational design of new lead anti-TB drugs. Structure-activity Relationship (SAR) is reported.

Synthesis and in vitro evaluation of neutral aryloximes as reactivators of Electrophorus eel acetylcholinesterase inhibited by NEMP, a VX surrogate

Casualties caused by nerve agents, potent acetylcholinesterase inhibitors, have attracted attention from media recently. Poisoning with these chemicals may be fatal if not correctly addressed. Therefore, research on novel antidotes is clearly warranted. Pyridinium oximes are the only clinically available compounds, but poor penetration into the blood-brain barrier hampers efficient enzyme reactivation at the central nervous system. In searching for structural factors that may be explored in SAR studies, we synthesized and evaluated neutral aryloximes as reactivators for acetylcholinesterase inhibited by NEMP, a VX surrogate. Although few tested compounds reached comparable reactivation results with clinical standards, they may be considered as leads for further optimization.

Calculation and experimental measurement of paramagnetic NMR parameters of phenolic oximate Cu(II) complexes

We present a strategy for predicting the unusual 1H and 13C shifts in NMR spectra of paramagnetic bisoximato copper(ii) complexes using DFT. We demonstrate good agreement with experimental measurements, although 1H-13C correlation spectra show that a combined experimental and theoretical approach remains necessary for full assignment.

Green and highly selective protocol for the synthesis of oximes

A green and efficient protocol has been developed for the synthesis of either exclusively a monoxime or exclusively a dioxime from a host of 1,2-dicarbonyl compounds on silica.

A general and convenient route to oxazolyl ligands

A diverse range of chiral and achiral oxazolyl ligands, which have many applications including catalysis and luminescent devices, are synthesized simply in three steps from readily available and inexpensive phenol and amino alcohol starting materials. The method can be applied to ligands with electron-donating/-withdrawing and sterically demanding/undemanding substituents, and can conveniently be scaled up to >25 g of product.

Characterization of scavengers of γ-ketoaldehydes that do not inhibit prostaglandin biosynthesis

Expression of cyclooxygenase-2 (COX-2) is associated with the development of many pathologic conditions. The product of COX-2, prostaglandin H2 (PGH2), can spontaneously rearrange to form reactive γ-ketoaldehydes called levuglandins (LGs). This γ-ketoaldehyde structure confers a high degree of reactivity on the LGs, which rapidly form covalent adducts with primary amines of protein residues. Formation of LG adducts of proteins has been demonstrated in pathologic conditions (e.g., increased levels in the hippocampus in Alzheimer's disease) and during physiologic function (platelet activation). On the basis of knowledge that lipid modification of proteins is known to cause their translocation and to alter their function, we hypothesize that modification of proteins by LG could have functional consequences. Testing this hypothesis requires an experimental approach that discriminates between the effects of protein modification by LG and the effects of cyclooxygenase-derived prostanoids acting through their G-protein coupled receptors. To achieve this goal, we have synthesized and evaluated a series of scavengers that react with LG with a potency more than 2 orders of magnitude greater than that with the ε-amine of lysine. A subset of these scavengers are shown to block the formation of LG adducts of proteins in cells without inhibiting the catalytic activity of the cyclooxygenases. Ten of these selective scavengers did not produce cytotoxicity. These results demonstrate that small molecules can scavenge LGs in cells without interfering with the formation of prostaglandins. They also provide a working hypothesis for the development of pharmacologic agents that could be used in experimental animals in vivo to assess the pathophysiological contribution of levuglandins in diseases associated with cyclooxygenase up-regulation.

Arylalkylamine vanadium (V) salts for the treatment and/or prevention of Diabetes mellitus

This invention provides compounds of formula (IIA) and pharmaceutical compositions thereof, where M, a, b, and R1-R5 are as defined herein, for treating human type 1 and type 2 diabetes, particularly insulin-resistant diabetes. Pharmaceutical compositions comprising the compounds of formula (IIA) are also disclosed.