76835-64-8

Basic information

• Product Name: methyl 3-oxododecanoate
• Synonyms: methyl 3-oxododecanoate;3-Ketolauric acid methyl ester;3-Oxododecanoic acid methyl ester;3-Oxolauric acid methyl ester;FHTQHJAYSZFNSI-UHFFFAOYSA-N
• CAS NO: 76835-64-8
• Molecular Formula: C₁₃H₂₄O₃
• Molecular Weight: 228.32786
• EINECS: 278-561-8
• Mol File: 76835-64-8.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 271.7°C at 760 mmHg
• Flash Point: 110.4°C
• Appearance: /
• Density: 0.936g/cm³
• Vapor Pressure: 0.00634mmHg at 25°C
• Refractive Index: 1.438
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: methyl 3-oxododecanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-oxododecanoate(76835-64-8)
• EPA Substance Registry System: methyl 3-oxododecanoate(76835-64-8)

Safety Data

• Hazardous Substances Data: 76835-64-8(Hazardous Substances Data)

Usage

Description

Methyl 3-oxododecanoate, also known as methyl 3-keto-dodecanoate, is a chemical compound with the molecular formula C13H24O3. It is a derivative of a fatty acid ester, specifically a methyl ester of 3-oxododecanoic acid. This organic compound is characterized by the presence of a carbonyl group (C=O) and a carboxyl group (COOH) in its structure, which makes it a versatile building block in organic synthesis.

Uses

Used in Organic Synthesis:
Methyl 3-oxododecanoate is used as a synthetic intermediate for the preparation of various organic compounds. Its reactivity and functional groups make it a valuable precursor in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in the Tethered Biginelli Reaction:
In the field of organic chemistry, methyl 3-oxododecanoate is specifically used in the tethered Biginelli reaction for the enantioselective synthesis of batzelladine alkaloids. Batzelladine alkaloids are a class of natural products with diverse biological activities, including anticancer, antiviral, and anti-inflammatory properties. The tethered Biginelli reaction is a multicomponent reaction that allows for the efficient and selective synthesis of these complex molecules, leveraging the unique reactivity of methyl 3-oxododecanoate as a key intermediate.

InChI:InChI=1/C13H24O3/c1-3-4-5-6-7-8-9-10-12(14)11-13(15)16-2/h3-11H2,1-2H3

Upstream product

• 13195-93-2 Ethyl decanoylacetoacetate 
• 124-41-4 sodium methylate 
• 67-56-1 methanol 
• 61058-75-1 3-oxo-dodecanoic acid 
• 182359-65-5 5-decanoyl-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 112-12-9 methyl nonyl ketone 
• 616-38-6 carbonic acid dimethyl ester 
• 112-31-2 caprinaldehyde 
• 6832-16-2 methyl diazoacetate 
• 111-83-1 1-bromo-octane 
• 105-45-3 acetoacetic acid methyl ester 
• 429675-23-0 5-(1-hydroxydecylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 112-13-0 n-decanoyl chloride 

Downstream Products

• 1883-13-2 3-hydroxydodecanoic acid 
• 56618-58-7 methyl (R)-3-hydroxydecanoate 
• 66997-66-8 (S)-methyl 3-hydroxydecanoate 
• 72864-23-4 β-hydroxydodecanoic acid methyl ester 
• 28254-78-6 (3R)-(-)-3-Hydroxydodecanoic acid 
• 76835-66-0 (R)-β-hydroxydodecanoic acid methyl ester 
• 66997-68-0 (S)-methyl 3-hydroxydodecanoate 
• 45162-48-9 (3S)-3-hydroxydodecanoic acid 
• 168982-69-2 N-(3-oxododecanoyl)-L-homoserine lactone 
• 596104-55-1 3-oxo-N-(2-oxocyclohexyl)dodecanamide 
• 862587-60-8 2-(2-nonyl-[1,3]dioxolan-2-yl)-N-(2-oxo-cyclohexyl)-acetamide 
• 157459-92-2 (R)-3-((2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-dodecanoic acid 
• 157459-93-3 (R)-3-((2R,3R,4S,5S,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-dodecanoic acid methyl ester 
• 1255649-56-9 methyl (E)-3-(p-toluenesulfonyloxy)-2-dodecenoate 

Relevant articles and documents

Profiling structural diversity and activity of 2-alkyl-4(1H)-quinoloneN-oxides ofPseudomonasandBurkholderia

We synthesized all major saturated and unsaturated 2-alkyl-4(1H)-quinoloneN-oxides ofPseudomonasandBurkholderia, quantified their native production levels and characterized their antibiotic activities against competingStaphylococcus aureus. We demonstrate that quinolone core methylation and position of unsaturation in the alkyl-chain dictate antibiotic potency which supports the proposed mechanism of action.

Quinolones modulate ghrelin receptor signaling: Potential for a novel small molecule scaffold in the treatment of cachexia

Cachexia is a metabolic wasting disorder characterized by progressive weight loss, muscle atrophy, fatigue, weakness, and appetite loss. Cachexia is associated with almost all major chronic illnesses including cancer, heart failure, obstructive pulmonary disease, and kidney disease and significantly impedes treatment outcome and therapy tolerance, reducing physical function and increasing mortality. Current cachexia treatments are limited and new pharmacological strategies are needed. Agonists for the growth hormone secretagogue (GHS-R1a), or ghrelin receptor, prospectively regulate the central regulation of appetite and growth hormone secretion, and therefore have tremendous potential as cachexia therapeutics. Non-peptide GHS-R1a agonists are of particular interest, especially given the high gastrointestinal degradation of peptide-based structures, including that of the endogenous ligand, ghrelin, which has a half-life of only 30 min. However, few compounds have been reported in the literature as non-peptide GHS-R1a agonists. In this paper, we investigate the in vitro potential of quinolone compounds to modulate the GHS-R1a in both transfected human cells and mouse hypothalamic cells. These chemically synthesized compounds demonstrate a promising potential as GHS-R1a agonists, shown by an increased intracellular calcium influx. Further studies are now warranted to substantiate and exploit the potential of these novel quinolone-based compounds as orexigenic therapeutics in conditions of cachexia and other metabolic and eating disorders.

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.