20707-70-4

Basic information

• Product Name: (Z,)-cinnamaldehyde oxime
• Synonyms: (Z,)-cinnamaldehyde oxime;Cinnamaldoxime;(1Z)-3-Phenylacrylaldehyde oxime;3-Phenylpropenal (Z)-oxime
• CAS NO: 20707-70-4
• Molecular Formula: C₉H₉NO
• Molecular Weight: 147.17386
• EINECS: 243-979-1
• Mol File: 20707-70-4.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 280.3°C at 760 mmHg
• Flash Point: 165.1°C
• Appearance: /
• Density: 0.97g/cm³
• Vapor Pressure: 0.00181mmHg at 25°C
• Refractive Index: 1.513
• CAS DataBase Reference: (Z,)-cinnamaldehyde oxime(CAS DataBase Reference)
• NIST Chemistry Reference: (Z,)-cinnamaldehyde oxime(20707-70-4)
• EPA Substance Registry System: (Z,)-cinnamaldehyde oxime(20707-70-4)

Safety Data

• Hazardous Substances Data: 20707-70-4(Hazardous Substances Data)

Usage

Description

(Z,)-cinnamaldehyde oxime, with the molecular formula C9H9NO and a molecular weight of 147.17 g/mol, is an oxime derivative of cinnamaldehyde found in the essential oil of cinnamon. It is a yellow liquid at room temperature, characterized by a strong, sweet, and floral odor. This chemical compound is recognized for its potential biological activities, such as antioxidant, anti-inflammatory, and antimicrobial properties, making it a promising candidate for various applications in the fields of pharmacology and medicine.

Uses

Used in Flavor and Fragrance Industry:
(Z,)-cinnamaldehyde oxime is used as a flavoring agent and fragrance in the food, perfume, and cosmetics industries due to its strong, sweet, and floral odor. Its unique scent and flavor profile contribute to enhancing the sensory experience of various products.
Used in Pharmaceutical Research:
(Z,)-cinnamaldehyde oxime is used as a subject of interest in the field of pharmacological and medical research for its potential biological activities. Its antioxidant, anti-inflammatory, and antimicrobial properties make it a valuable compound for exploring new therapeutic approaches and treatments.
Used in Antioxidant Applications:
(Z,)-cinnamaldehyde oxime is used as an antioxidant agent for its ability to combat oxidative stress and protect cells from damage. This application is particularly relevant in the development of novel pharmaceuticals and nutraceuticals aimed at promoting overall health and well-being.
Used in Anti-Inflammatory Applications:
(Z,)-cinnamaldehyde oxime is used as an anti-inflammatory agent, leveraging its potential to reduce inflammation and alleviate pain. This application is significant in the development of new medications for conditions characterized by chronic inflammation, such as arthritis and other autoimmune diseases.
Used in Antimicrobial Applications:
(Z,)-cinnamaldehyde oxime is used as an antimicrobial agent, given its ability to inhibit the growth of harmful microorganisms. This property makes it a valuable component in the development of new antimicrobial products, such as disinfectants, sanitizers, and preservatives, particularly in the healthcare and food industries.

InChI:InChI=1/C9H9NO/c11-10-8-4-7-9-5-2-1-3-6-9/h1-8,11H/b7-4-,10-8u

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 1028432-12-3 C₂₂H₃₁NO₃SSi 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 4335-60-8 (E)-cinnamylamine 
• 96-29-7 ethyl methyl ketone oxime 
• 104-55-2 3-phenyl-propenal 
• 524-38-9 N-hydroxyphthalimide 

Downstream Products

• 4335-60-8 (E)-cinnamylamine 
• 140-10-3 (E)-3-phenylacrylic acid 
• 21737-13-3 (E)-styrylaldehyde oxime 
• 4360-47-8 cinnamonitrile 
• 69415-53-8 benzoyl cinnamaldehyde oxime 
• 131934-06-0 3,3-Diphenyl-propionaldehyde oxime 
• 87094-78-8 (E)-2-(2-phenylethenyl)-1,3-dithiolane 
• 14371-10-9 (E)-3-phenylpropenal 
• 1885-38-7 cinnamic nitrile 
• 2038-57-5 3-Phenylpropan-1-amine 
• 621-82-9 Cinnamic acid 
• 380916-46-1 C₁₇H₁₇ClN₂O₃S 

Relevant articles and documents

Selective and facile synthesis of α,β-unsaturated nitriles and amides with N-hydroxyphthalimide as the nitrogen source

The direct conversion of α,β-unsaturated aldehydes to corresponding nitriles promoted by Pd(OAc)2 and phthalic acid which was hydrolyzed from N-hydroxyphthalimide (NHPI) has been disclosed. Additionally, it was found that when water was used as the solvent, α,β-unsaturated amides was obtained as the main products in good to excellent yields. It was first reported that NHPI was utilized as the nitrogen source to synthesize α,β-unsaturated nitriles and amides from aldehydes. Control experiment demonstrated that aldehydes undergo a process of oximation and dehydration to form nitriles and amides.

Br?nsted acid catalyzed transoximation reaction: Synthesis of aldoximes and ketoximes without use of hydroxylamine salts

The transoximation reaction enables the transfer of an oxime to a carbonyl compound and is catalyzed by transoximase in the pupae of the silkworm. Inspired by this bio-synthetic pathway, we achieved the transoximation of oximes to aldehydes and ketones catalyzed by a Br?nsted acid under mild conditions. Hydroxylamine salt, which necessitates a stoichiometric amount of base, was not required. NMR analysis clarified that this reaction proceeded through hydroxylamines generated by the successive hydrolysis of the oxime in situ. In addition, an environmentally benign method for catalytic transoximation was demonstrated in aqueous medium on a one hundred gram scale and the reaction filtrate containing the catalyst was recovered and reused over 10 times.

A novel and efficient catalytic system including TEMPO/acetaldoxime/InCl3 for aerobic oxidation of primary amines to oximes

A simple and efficient catalytic system including TEMPO/acetaldoxime/InCl3 for aerobic oxidation of primary amines to corresponding oximes by using toluene as the solvent is described. This practical method can use O2 as the economic and green oxidant, tolerate a wide range of substrates, which can afford the target oximes in moderate to excellent yields.