22348-96-5

Basic information

• Product Name: methyl 3-oxodecanoate
• Synonyms: 3-Ketocapric acid methyl ester;3-Oxodecanoic acid methyl ester;Decanoic acid, 3-oxo-, methyl ester;Einecs 244-928-6
• CAS NO: 22348-96-5
• Molecular Formula: C₁₁H₂₀O₃
• Molecular Weight: 200.27
• EINECS: 244-928-6
• Product Categories: Mixed Fatty Acids;Fatty Acid Derivatives & Lipids;Glycerols
• Mol File: 22348-96-5.mol

Chemical Properties

• Boiling Point: 92-98°C/0.5mm
• Flash Point: 98.5 °C
• Appearance: colorless to slight yellow liquid
• Density: 0.95 g/cm³
• Vapor Pressure: 0.0282mmHg at 25°C
• Refractive Index: 1.433
• Storage Temp.: Refrigerator
• CAS DataBase Reference: methyl 3-oxodecanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-oxodecanoate(22348-96-5)
• EPA Substance Registry System: methyl 3-oxodecanoate(22348-96-5)

Safety Data

• Hazardous Substances Data: 22348-96-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Methyl 3-oxodecanoate is used as a key intermediate in the synthesis of various organic compounds for different industries. Its reactivity and functional groups allow it to participate in a wide range of chemical reactions, making it a valuable building block for creating new molecules and materials.
Used in Fragrance Industry:
Methyl 3-oxodecanoate is used as a fragrance ingredient in the perfumery and cosmetics industry. Its unique scent profile and stability contribute to the creation of various fragrances, enhancing the sensory experience of products.
Used in Pharmaceutical Industry:
Methyl 3-oxodecanoate is used as a starting material or intermediate in the synthesis of pharmaceutical compounds. Its versatility in organic synthesis allows for the development of new drugs and active pharmaceutical ingredients.
Used in Flavor Industry:
Methyl 3-oxodecanoate is used as a flavoring agent in the food and beverage industry. Its distinct taste and aroma characteristics can be utilized to create unique flavor profiles, enhancing the overall taste experience of various products.
Used in Agrochemical Industry:
Methyl 3-oxodecanoate is used as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its role in creating these compounds contributes to the development of effective solutions for crop protection and management.

InChI:InChI=1/C11H20O3/c1-3-4-5-6-7-8-10(12)9-11(13)14-2/h3-9H2,1-2H3

Upstream product

• 67-56-1 methanol 
• 103576-44-9 2,2-dimethyl-5-octanoyl-1,3-dioxane-4,6-dione 
• 124-12-9 caprylnitrile 
• 96-32-2 bromoacetic acid methyl ester 
• 821-55-6 2-Nonanone 
• 616-38-6 carbonic acid dimethyl ester 
• 13283-92-6 β-ketodecanoic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 66696-81-9 5-(1-hydroxyoctylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 124-07-2 Octanoic acid 
• 38330-80-2 monomethyl monopotassium malonate 
• 2033-24-1 cycl-isopropylidene malonate 
• 111-64-8 n-octanoic acid chloride 
• 79-20-9 acetic acid methyl ester 

Downstream Products

• 5561-87-5 3-hydroxydecanoic acid 
• 2503-80-2 4-hydroxy-2-heptylquinoline 
• 19526-23-9 3-(S)-hydroxydecanoic acid 
• 56618-58-7 methyl (R)-3-hydroxydecanoate 
• 66997-66-8 (S)-methyl 3-hydroxydecanoate 
• 821-55-6 2-Nonanone 
• 13283-92-6 β-ketodecanoic acid 
• 147795-40-2 N-(3-oxodecanoyl)-L-homoserine lactone 
• 206359-73-1 (S)-2-(Trityl-amino)-propionic acid (S)-1-((2S,3S)-3-decyl-4-oxo-oxetan-2-ylmethyl)-octyl ester 
• 40522-46-1 2-heptyl-quinolin-4(1H)-one 
• 1309782-10-2 C₄₅H₆₀N₄O₉ 
• 1309782-00-0 C₄₈H₆₁N₅O₁₀ 
• 1309782-11-3 C₄₈H₆₁N₅O₁₀ 
• 1309781-88-1 C₃₄H₄₉N₅O₁₀ 

Relevant articles and documents

Synthesis and biological activity of methylated derivatives of the Pseudomonas metabolites HHQ, HQNO and PQS

Selectively methylated analogues of naturally occurring 2-heptyl-4(1H)-quinolones, which are alkaloids common within the Rutaceae family and moreover are associated with quorum sensing and virulence of the human pathogen Pseudomonas aeruginosa, have been prepared. While the synthesis by direct methylation was successful for 3-unsubstituted 2-heptyl-4(1H)-quinolones, methylated derivatives of the Pseudomonas quinolone signal (PQS) were synthesized from 3-iodinated quinolones by methylation and iodine–metal exchange/oxidation. The two N- and O-methylated derivatives of the PQS showed strong quorum sensing activity comparable to that of PQS itself. Staphylococcus aureus, another pathogenic bacterium often co-occurring with P. aeruginosa especially in the lung of cystic fibrosis patients, was inhibited in planktonic growth and cellular respiration by the 4-O-methylated derivatives of HQNO and HHQ, respectively.

Application of the Tethered Biginelli reaction for enantioselective synthesis of batzelladine alkaloids. Absolute configuration of the tricyclic guanidine portion of batzelladine B

Tethered Biginelli condensation of enantioenriched hexahydropyrrolopyrimidines 8 with β-ketoesters provides efficient asymmetric access to tricyclic guanidines 9 having a syn relationship of the angular C2a and C8a hydrogens. This reaction was employed to realize the first practical enantioselective access to this fragment of batzelladine alkaloids B (2) and E (5). The efficiency of this strategy is illustrated in the synthesis of the dextrorotatory enantiomer of batzelladine B methanolysis product 10 in 10 steps and 25% overall yield from 2-nonanone and methyl acetoacetate. The asymmetric synthesis of 1.0 establishes that the absolute configuration of the tricyclic portion of batzelladine B (2) is 25aR,28S,30R. The 4-methyl-7-alkyl-1,2,2a,3,4,5,6,7,8,8a-decahydro-5,6,8b- triazaacenaphthalene-3-carboxylic acid subunit, e.g., 29, of batzelladine alkaloids A (1), D (4), F (6), and G was also prepared for the first time by catalytic hydrogenation of tricyclic guanidines 26 having the 2a,8a-anti stereochemistry.

IN VITRO METHOD FOR DETECTION OF INFECTIONS CAUSED BY PSEUDOMONAS AERUGINOSA

In vitro method for detection of infections caused by pseudomonas aeruginosa. The present invention relates to compounds of general Formula (I) and to their use as haptens. Moreover, the present invention also refers to conjugates comprising the haptens of the invention and to their use for obtaining antibodies. Finally, the invention also relates to an in vitro method for the detection of infections caused by Pseudomonas aeruginosa by means of the identification and/or quantification of the main signaling molecules from the pqs quorum sensing system.

COMPOUND FOR USE AGAINST PATHOGENIC NEISSERIA AND HAEMOPHILUS SPECIES AND MORAXELLA CATARRHALIS

The present invention relates to a compound, which can be used in the prevention and treatment of infections with pathogenic Neisseria species, in particular N. gonorrhoeae and N. meningitidis (the gonococcus and the meningococcus, respectively), and other pathogenic bacteria (e.g. Haemophilus species or Moraxella catarrhalis ), and which can be used for disinfecting a substrate from said bacteria. Moreover, the present invention relates to a corresponding pharmaceutical composition comprising said compound.

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.

An Unsaturated Quinolone N-Oxide of Pseudomonas aeruginosa Modulates Growth and Virulence of Staphylococcus aureus

The pathogen Pseudomonas aeruginosa produces over 50 different quinolones, 16 of which belong to the class of 2-alkyl-4-quinolone N-oxides (AQNOs) with various chain lengths and degrees of saturation. We present the first synthesis of a previously proposed unsaturated compound that is confirmed to be present in culture extracts of P. aeruginosa, and its structure is shown to be trans-Δ1-2-(non-1-enyl)-4-quinolone N-oxide. This compound is the most active agent against S. aureus, including MRSA strains, by more than one order of magnitude whereas its cis isomer is inactive. At lower concentrations, the compound induces small-colony variants of S. aureus, reduces the virulence by inhibiting hemolysis, and inhibits nitrate reductase activity under anaerobic conditions. These studies suggest that this unsaturated AQNO is one of the major agents that are used by P. aeruginosa to modulate competing bacterial species.

COMPOUNDS FOR USE AS AN ANTI-BACTERIAL OR ANTI-FUNGAL AGENT AND AS A ZINC SENSOR

The present invention relates to a compound, which can be used as an anti-bacterial and/or an anti-fungal agent as well as a zinc sensor. Moreover, the present invention relates to a pharmaceutical composition comprising said compound and methods for treating bacterial or fungal infections in mammals.

The requirements at the C-3 position of alkylquinolones for signalling in Pseudomonas aeruginosa

The 'perfect storm' of increasing bacterial antibiotic resistance and a decline in the discovery of new antibiotics, has made it necessary to search for new and innovative strategies to treat bacterial infections. Interruption of bacterial cell-to-cell communication signalling (Quorum Sensing), thus neutralizing virulence in pathogenic bacteria, is a growing area. 2-Alkyl-4-quinolones, HHQ and PQS, play a key role in the quorum sensing circuitry of P. aeruginosa. We report a new set of isosteres of 2-heptyl-6-nitroquinolin-4-one, with alterations at C-3, and evaluate the key structural requirements for agonistic and antagonistic activity in Pseudomonas aeruginosa.

Isolation of the antibiotic pseudopyronine B and SAR evaluation of C3/C6 alkyl analogs

Natural products are an abundant source of structurally diverse compounds with antibacterial activity that can be used to develop new and potent antibiotics. One such class of natural products is the pseudopyronines. Here we present the isolation of pseudopyronine B (2) from a Pseudomonas species found in garden soil in Western North Carolina, and SAR evaluation of C3 and C6 alkyl analogs of the natural product for antibacterial activity against Gram-positive and Gram-negative bacteria. We found a direct relationship between antibacterial activity and C3/C6 alkyl chain length. For inhibition of Gram-positive bacteria, alkyl chain lengths between 6 and 7 carbons were found to be the most active (IC50?=?0.04–3.8?μg/mL) whereas short alkyl chain analogs showed modest activity against Gram-negative bacteria (IC50?=?223–304?μg/mL). This demonstrates the potential for this class of natural products to be optimized for selective activity against either Gram-positive or Gram-negative bacteria.

MACROCYCLIC BROAD SPECTRUM ANTIBIOTICS

Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of bacterial type 1 signal peptidase (SpsB), an essential protein in bacteria. Pharmaceutical compositions and methods for treatment using the compounds described herein are also provided.