14531-34-1

Usage

Uses

Used in Flavor and Fragrance Industry:
Methyl 3-oxooctadecanoate is utilized as a flavoring agent in food products for its fruity scent, enhancing the taste and aroma of various culinary creations.
Used in Cosmetics and Perfumery:
In the cosmetics and perfumery industry, methyl 3-oxooctadecanoate serves as a key ingredient in the production of perfumes and other fragranced products, contributing to their distinct and appealing scents.
Used in Organic Synthesis:
Due to its reactivity as a carbonyl compound, methyl 3-oxooctadecanoate is employed in the synthesis of a range of organic compounds, playing a crucial role in chemical research and the development of new materials.
Used in Antimicrobial Applications:
Methyl 3-oxooctadecanoate is recognized for its antimicrobial properties, making it a potential candidate for use in applications requiring the inhibition of microbial growth, such as in certain pharmaceutical or medical products.
Used in Antioxidant Formulations:
Leveraging its antioxidant properties, methyl 3-oxooctadecanoate can be incorporated into formulations designed to protect against oxidative stress, which may be beneficial in various health and industrial applications.

InChI:InChI=1/C19H36O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-18(20)17-19(21)22-2/h3-17H2,1-2H3

Upstream product

• 95806-04-5 2-acetyl-3-oxo-octadecanoic acid ethyl ester 
• 124-41-4 sodium methylate 
• 19218-94-1 1-iodotetradecane 
• 105-45-3 acetoacetic acid methyl ester 
• 38330-80-2 monomethyl monopotassium malonate 
• 112-67-4 n-hexadecanoyl chloride 
• 67-56-1 methanol 
• 57-10-3 1-hexadecylcarboxylic acid 
• 2033-24-1 cycl-isopropylidene malonate 
• 1224514-12-8 C₂₁H₃₈O₃ 
• 103590-58-5 5-Hexadecanoyl-2,2-dimethyl-[1,3]dioxane-4,6-dione 

Downstream Products

• 107649-71-8 2-hydroxyimino-3-oxo-octadecanoic acid methyl ester 
• 17773-30-7 3-hydroxyoctadecanoic acid 
• 16694-29-4 3-oxooctadecanoic acid 
• 2420-36-2 (R)-β-hydroxyoctadecanoic acid methyl ester 
• 14531-45-4 (S)-β-hydroxyoctadecanoic acid methyl ester 
• 13552-09-5 2-aminooctadecan-1,3-diol 
• 1363461-93-1 methyl (R)-3-benzyloxyoctadecanoate 
• 1363461-56-6 (R)-3-(benzyloxy)octadecanoic acid 
• 1584233-97-5 N-acetyl-5-benzylidene-3-hexadecanoyltetramic acid 
• 13031-64-6 (2S,3R)-2-acetylaminooctadecan-1,3-diol 
• 35301-24-7 C2-dihydroceramide 
• 56586-44-8 (2S:3R)-2-benzamino-octadecanediol-(1.3) 

Relevant academic research and scientific papers

Facile synthesis of β-keto esters from methyl acetoacetate and acid chloride: The barium oxide/methanol system

The synthesis of β-keto esters has been performed in good yield by reacting excess methyl acetoacetate with barium oxide, acylating the resulting barium complex with acid chloride, and then cleaving the α-acyl β-keto ester with methanol at a mild temperature. Using this new procedure, various β-keto esters were prepared. Thus, methyl 4-phenyl-3-oxobutanoate, methyl 3-phenyl-3-oxopropionate, methyl 4-cyclohexyl-3-oxobutanoate, and methyl 3-oxooctadecanoate were prepared from methyl acetoacetate and the corresponding acid chloride in 69%, 84%, 67%, and 74% yields, respectively.

Synthesis and antitumoral activity of novel analogues monastrol-fatty acids against glioma cells

Monastrol is a small cell-permeable heterocyclic molecule that is recognized as an inhibitor of mitotic kinesin Eg5. Heterocyclic-fatty acid derivatives are a new class of compounds with a broad range of biological activities. This work describes a comparative study of the in vitro antitumoral activity of a series of new long-chain monastrol analogues against rat glioblastoma cells. The novel analogues C6-substituted monastrol and oxo-monastrol were synthesized via Biginelli multicomponent condensation of fatty β-ketoester in good yields using a simple approach catalyzed by nontoxic and free-metal sulfamic acid. Following synthesis, their in vitro antitumoral activities were investigated. Notably, all analogues tested were active against rat glioblastoma cells. Superior activity was observed by analogues derived from palmitic and stearic fatty acid chains; these compounds were the most potent molecules, showing 13-fold higher potency than monastrol with IC50 values of 5.11 and 6.85 μM, respectively. These compounds could provide promising new lead derivatives for more potent antitumor drugs.

Asymmetric Reduction of 3-Oxo-octadecanoic Acid with Fermenting Baker's Yeast. An Easy Synthesis of Optically Pure (+)-(2R,3R)-Corynomycolic Acid

Optically pure (+)-corynomycolic acid has been synthesized from methyl acetoacetate by a route including asymmetric reduction of 3-oxo-octadecanoic acid with baker's yeast as a key step.

Evaluation of the antioxidant activities of fatty polyhydroquinolines synthesized by Hantzsch multicomponent reactions

Polyhydroquinolines (PHQs) are the unsymmetrical Hantzsch derivatives of 1,4-dihydropyridines with several biological applications. In this work, new fatty 2- and 3-substituted PHQ derivatives from different fatty acids and fatty alcohol feedstocks were synthesized at good yields via a four-component reaction (4CR). The antioxidant activities of fatty PHQs were investigated using three different antioxidant methods. The experiments showed that the compounds derived from 2-nitrobenzaldehyde and fatty palmitic (C16:0) and oleic (C18:1) chains showed better antioxidant activity. This revealed that combining the ortho NO2 group in the aromatic ring with the insertion of fatty chains in the PHQ core contributed to the antioxidant activity. However, among all the fatty PHQs tested, the fatty 2-substituted compound derived from oleyl alcohol and 2-nitrobenzaldehyde showed the highest antioxidant activity (EC50, 2.11-4.69 μM), which was similar to those of the antioxidant standards butylated hydroxytoluene (EC50, 1.98-6.47 μM) and vitamin E (EC50, 1.19-5.88 μM). In addition, this lipophilic compound showed higher antioxidant activity than the antihypertensive drug nifedipine (EC50, 49.25-126.86 μM). These results indicate that the new fatty PHQs may find novel applications as antioxidant additives.

Preparation of the even-numbered 3-oxo fatty acid nicotinyl esters from C6:0 to C18:0

Here, we report a systematic comparison of different methods for the transesterification of 3-oxo fatty acid alkyl esters to the corresponding nicotinyl esters. A simple method producing the target esters in high yields and purity has been developed. Nicotinyl esters are of interest for mass spectrometry analysis of fatty acids. Also, the hydrophilic head group of nicotinyl esters can be used as the basis for the preparation of liposome-building molecules.

Synthesis of β-ketoesters from renewable resources and Meldrum's acid

β-Ketoesters are valuable building blocks for the synthesis of compounds with different biological activities. In this study, a series of fatty β-ketoesters were obtained from fatty acids and Meldrum's acid using N,N-dicyclohexylcarbodiimide and dimethylaminopyridine. In addition, we demonstrate for the first time the synthesis of new fatty β-ketoesters from oleic (cis-C18:1), elaidic (trans-C18:1), ricinoleic (cis-C18:1, 12-OH), linoleic (cis,cis-C18:2), and linolenic (cis,cis,cis-C18:3) acids in good yields.

Hydroxy fatty acids for the delivery of dideoxynucleosides as anti-HIV agents

A series of α- and β-carboxylated phospholipid prodrugs of dideoxy nucleosides have been synthesized and evaluated against HIV. An increase in biological effect with a factor of 500 has only been observed for the adenine nucleoside, which suggests that this prodrug approach is base specific.

Synthesis and chain-dependent antifungal activity of long-chain 2H-azirine-carboxylate esters related to dysidazirine

Analogues of the antifungal marine natural product (E)-dysidazirine were prepared and evaluated in broth ro-dilution assays against a panel of fungal pathogens. A simple structure-activity relationship was developed which provides insight into the mechanism of action of long-chain 2H-azirine carboxylates.

Dynamic kinetic resolution: An efficient route to anti α-amino- β-hydroxy esters via Ru-SYNPHOS catalyzed hydrogenation

The Ru(II)-catalyzed hydrogenation of α-amino-β-keto esters as their hydrochloride salts affords preparation of the corresponding anti α-amino-β-hydroxy esters under mild conditions with high diastereoselectivities and enantioselectivities via dynamic kinetic resolution.

Enantioselective Hydrogenation of β-Keto Esters using Chiral Diphosphine-Ruthenium Complexes: Optimization for Academic and Industrial Purposes and Synthetic Applications

Enantioselective hydrogenation using chiral complexes between atropisomeric diphosphines and ruthenium is a powerful tool for producing chiral compounds. Using a simple and straightforward in situ catalyst preparation, the conditions were optimized using molecular hydrogen for both academic and industrial purposes. This led to the best conditions and the lowest catalytic ratio required for the pressure used. Hydrogenation of various β-keto esters was efficiently performed at atmospheric and higher pressures, leading to the use of very low catalyst-substrate ratios up to 1/20,000. Asymmetric hydrogenations were used in key-steps towards the total synthesis of corynomycolic acid, Duloxetine and Fluoxetine.