19150-71-1

Basic information

• Product Name: octadecyl acetoacetate
• Synonyms: octadecyl acetoacetate;NSC406330;3-Oxobutanoic acid octadecyl ester;Acetoacetic acid octadecyl ester;3-Benzoyl-4-hydroxycouMarin
• CAS NO: 19150-71-1
• Molecular Formula: C₂₂H₄₂O₃
• Molecular Weight: 354.56708
• EINECS: 242-844-4
• Mol File: 19150-71-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 378.4°Cat760mmHg
• Flash Point: 154.8°C
• Appearance: /
• Density: 0.903g/cm³
• Vapor Pressure: 6.3E-06mmHg at 25°C
• Refractive Index: 1.451
• CAS DataBase Reference: octadecyl acetoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: octadecyl acetoacetate(19150-71-1)
• EPA Substance Registry System: octadecyl acetoacetate(19150-71-1)

Safety Data

• Hazardous Substances Data: 19150-71-1(Hazardous Substances Data)

Usage

General Description

Octadecyl acetoacetate is a synthetic chemical compound with the molecular formula C22H42O3. It is derived from acetoacetic acid and octadecanol, and is primarily used as a plasticizer and lubricant in various industrial applications. It is commonly added to polymers, coatings, and adhesives to improve flexibility, durability, and surface smoothness. Octadecyl acetoacetate has low volatility and high thermal stability, making it suitable for use in high-temperature applications. It also has good resistance to chemicals and weathering, making it useful in outdoor and harsh environments. However, it is important to handle this chemical with care and follow proper safety precautions due to its potential health and environmental hazards.

InChI:InChI=1/C22H42O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-25-22(24)20-21(2)23/h3-20H2,1-2H3

Upstream product

• 112-92-5 1-octadecanol 
• 141-97-9 ethyl acetoacetate 
• 105-45-3 acetoacetic acid methyl ester 
• 674-82-8 4-methyleneoxetan-2-one 

Downstream Products

• 20634-52-0 3-amino-crotonic acid octadecyl ester 

Relevant articles and documents

Novel hybrid DHPM-fatty acids: Synthesis and activity against glioma cell growth in vitro

We described the first synthesis of fatty acid 3,4-dihydropyrimidinones (DHPM-fatty acids) using the Biginelli multicomponent reaction. Antiproliferative activity on two glioma cell lines (C6 rat and U-138-MG human) was also reported. The novel DHPM-fatty acids reduced glioma cell viability relative to temozolomide. Hybrid oxo-monastrol-palmitic acid was the most potent, reducing U-138-MG human cell viability by ca. 50% at 10 1/4M. In addition, the DHPM-fatty acids showed a large safety range to neural cells, represented by the organotypic hippocampal culture. These results suggest that the increased lipophilicity of DHPM-fatty acids offer a promising approach to overcoming resistance to chemotherapy and may play an important role in the development of new antitumor drugs.

Synthesis of Fatty Acetoacetates Under Microwave Irradiation Catalysed by Sulfamic Acid in a Solvent-Free System

The 1,3-dicarbonyl compounds are important building blocks to obtain products with various biological activities and technological applications. In this work, we used a simple transesterification method to develop fatty acetoacetates in a solvent-free medium using a green catalyst, sulfamic acid (NH2SO3H), under microwave irradiation. The experimental results demonstrate good yields in a short reaction time (13?min), which makes this method an efficient approach to synthesize fatty acetoacetates from a wide range of saturated, unsaturated, and polyunsaturated long chain fatty alcohols, and ricinoleic derivatives. Experiments of recycling of the catalyst were performed and no decrease in catalytic activity of sulfamic acid was observed.

Nucleophilic acyl substitutions of esters with protic nucleophiles mediated by amphoteric, oxotitanium, and vanadyl species

(Chemical Equation Presented) A diverse array of oxometallic species were examined as catalysts in nucleophilic acyl substitution (NAS) reactions of methyl (or ethyl) esters with protic nucleophiles. Among them, oxotitanium acetylacetonate (TiO(acac)2) and vanadyl chloride (VOCl 2-(THF)x) served as the most efficient and water-tolerant catalysts. Transesterifications of methyl and/or ethyl esters with functionalized (including acid- or base-sensitive) 1° and 2° alcohols can be carried out chemoselectively in refluxed toluene or xylene in a 1:1 substrate stoichiometry using 1 mol % catalyst loading. The resultant products were furnished in 85-100% yields by simple aqueous workup to remove water-soluble catalysts. The new NAS protocol is also amenable to amines and thiols in 74-91% yields, albeit with higher loading (2.5 equiv) of protic nucleophiles. Representative examples of commercial interests such as Padimate O and antioxidant additives for plastics were also examined to demonstrate their practical applications. A 1:1 adduct between TiO(acac)2 and a given 1-octadecanol was identified as (C18H37O) 2Ti(acac)2 and was responsible for its subsequent NAS of methyl esters.