2575-01-1

Usage

Uses

Used in Pharmaceutical Industry:
9-keto-2-decenoic acid is used as an anti-inflammatory and immunomodulatory agent for its potential therapeutic applications in treating autoimmune diseases and other inflammatory conditions.
Used in Antimicrobial Applications:
9-keto-2-decenoic acid is used as an anti-bacterial and anti-fungal agent for its potential to treat infections caused by various microorganisms.
Used in Antioxidant Applications:
9-keto-2-decenoic acid is used as an antioxidant for its potential to protect the body from oxidative stress and related cellular damage.
Further study of 9-keto-2-decenoic acid may lead to the development of new treatments for a variety of health conditions.

Upstream product

• 2575-06-6 Decen-(2^c+t)-on-⁽⁹⁾-saeure-⁽¹⁾-methylester 
• 65127-45-9 (Z)-9-Oxo-dec-2-enoic acid ethyl ester 
• 2104-05-4 2-mercapto-4-(4'-methoxyphenyl)thiazole 
• 96181-65-6 Decen-(2^c+t)-on-⁽⁹⁾-saeure-⁽¹⁾-aethylenketal 
• 872-01-5 trans-Nonen-8-in-carbonsaeure, Dec-9-in-trans-2-ensaeure 
• 57221-88-2 ethyl 9-oxo-trans-2-decenoate 
• 36219-80-4 7-oxo-octanal 
• 66130-90-3 diethyl <<(trimethylsilyl)oxy>carbonyl>methanephosphonate 
• 3695-28-1 5-iodo-2-pentanone ethylene ketal 
• 64196-68-5 (Z)-4-acetoxy-2-buten-1-ol 
• 1189-64-6 (E)-9-Oxo-2-decanoic acid methyl ester 
• 65946-59-0 (trimethylsilyl)ketene bis(trimethylsilyl) acetal 
• 57221-86-0 6-(2-methyl-1,3-dioxolan-2-yl)-hexanal 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 1189-64-6 (E)-9-Oxo-2-decanoic acid methyl ester 
• 91882-58-5 9-hydroxy-(E)-2-decenoic acid 
• 83944-98-3 (S,E)-(+)-9-hydroxydec-2E-enoic acid 
• 4448-33-3 (E)-(+/-)-9-Hydroxy-2-decensaeure 
• 90973-03-8 Decen-(2^t)-on-⁽⁹⁾-saeure-⁽¹⁾-chlorid 
• 1422-26-0 9-oxodecanoic acid 
• 757219-33-3 2E-nonene-1,9-dioic acid 
• 334-48-5 1-decanoic acid 
• 3208-05-7 decane-1,9-diol 

Relevant academic research and scientific papers

INSECT PHEROMONES AND THEIR ANALOGS. IV. THE SYNTHESIS OF THE SEX ATTRACTANT OF THE HONEY BEE Apis mellifera

A new and convenient method for the synthesis of 9-oxodec-2E-enoic acid (I) from the readily accessible octa-2E,7-dienyl acetate is proposed.From the latter compound by a series of transformations (oxidation of the terminal double bond to a ketone, saponification, hydrogenation, and oxidation with Corey's reagent) 7-oxooctanal is obtained, and this is condensed by the Knoevenagel reaction with malonic acid to give compound (I) with a yield of 69percent.

New approach to the synthesis of 9-oxo-2E-decenoic acid, a multifunctional pheromone of queen honeybee, from the telomer of butadiene and water

A new approach was proposed for the synthesis of 9-oxo-2E-decenoic acid, a multifunctional pheromone of queen honeybee (Apis mellifera L.), starting from the available telomer of butadiene and water (2E,7-octadien-1-ol) using in the key steps partial ozonolysis of the corresponding carbonyl compound, selective oxidation of the conjugated aldehyde into a carboxylic acid, and alkylation of acetoacetic ester to introduce the oxo group.

A two-step synthesis of the 'Queen substance' of the honey bee

A synthesis of the 'queen substance' was accomplished in two steps from readily available starting materials. The key step was a novel one-pot reduction of 7-oxooctanoic acid to 7-oxooctanal followed by condensation with malonic acid.

INSECT PHEROMONES AND THEIR ANALOGS. XV. THE SYNTHESIS OF 9-OXODEC-2E-ENOIC ACID - A PHEROMONE OF THE HONEYBEE Apis melliferana

A new effective route to the synthesis of 7-oxooctanal has been found which is based on the ozonolysis of the tetrahydropyran-2-yl ether of 7-methyloct-7-en-1-ol - the product of the coupling of the readily available methallyl chloride and the Grignard reagent from the corresponding ether of 5-bromopentan-1-ol.From the 7-oxooctanal has been obtained 9-oxodec-2E-enoic acid - a pheromone of the honeybee Apis melliferana.

Lithiated anions derived from (alkenyl)pentamethyl phosphoric triamides: Useful synthons for the stereoselective synthesis of 9-oxo- and 10-hydroxy-2(E)-decenoic acids, important components of queen substance and royal jelly of honeybee Apis mellifera

Lithiated anions derived from (alkenyl)pentamethyl phosphoric triamides as homoenolate equivalents are used in the reaction with halogenated acetal and ketal giving regioselectively the γ-alkylation adducts. Chemoselective acidic hydrolysis of the enephosphoramide moiety in the presence of acetal or ketal groups leads to expected carbonyl products, key intermediates in the synthesis of natural compounds. The synthetic potential of the presented strategy is illustrated by stereoselective synthesis of two pheromones namely, 9-oxo-2(E)-decenoic acid 1 from queen substance and 10-hydroxy-2(E)-decenoic acid 2 from royal jelly of honeybee Apis mellifera.

Practical synthesis of (E)-α,β-unsaturated carboxylic acids using a one-pot hydroformylation/decarboxylative Knoevenagel reaction sequence

Combining the regioselective room temperature/ambient pressure hydroformylation and a modification of the Doebner-Knoevenagel reaction allowed for the development of an efficient, one-pot procedure for the synthesis of (E)-α,β-unsaturated carboxylic acids. The reaction proceeds under mild conditions, tolerates a variety of functional groups and gives (E)-α,β-unsaturated carboxylic acids in good yields and with excellent regio-and stereocontrol. The practicability of this process has been demonstrated by a short protecting group-free synthesis of the queen honeybee pheromones 9-ODA[( E)-9-oxodec-2-enoic acid] and 9-HDA[( E)-9-hydroxydec-2-enoic acid].

Synthesis of a multifunctional pheromone of the honeybee Apis mellifera via condensation of 7-oxooctanal with malonic acid

Condensation of 7-oxooctanal with malonic acid in a Doebner reaction produces 9-oxo-2E-decenoic acid (42% yield) and a comparable amount of products from Tishchenko disproportionation of the starting aldehyde (7-oxooctyl-7- oxooctanoate) and re-esterification by acetic acid (7-oxooct-1-ylacetate and 7-oxooctanoic acid).

Composition, method, and apparatus to attract bees

Applicant's invention includes an improved bee attracting composition. Applicant's invention further includes a bee attracting device formed from his improved bee attracting composition. Applicant's bee attracting device can be further coated with a second bee attracting composition. Applicant's invention further includes a method and apparatus for attracting and immobilizing bees using a substrate coated with an adhesive composition upon which Applicant's bee attracting composition is disposed.

Synthesis of 10-hydroxy- and 9-oxo-2E-decenoic acids from oleic acid

A practical synthesis of biologically active 10-hydroxy- and 9-oxo-2E-decenoic acids, components of mandibular gland secretion of honeybee (Apis mellifera L.), is developed using ozonolysis - reduction of oleic acid and 1,9-diacetoxynon-1-ene in the key steps.

Tungsten(0) alkylidene complexes stabilized as pyridinium ylides: New aspects of their synthesis and reactivity

The interaction of dihydropyridines with alkoxycarbene complexes of tungsten has been shown to lead to pyridinium ylid complexes: this transformation has now been applied to the synthesis of a hydroxyl-containing ylid complex by ring-opening of the pentacarbonyl (2-oxacyclopentylidene) tungsten(0) complex and to the synthesis of a series of chiral ylid complexes both from chiral and non-chiral carbene complexes by the use of dihydropyridines and dihydronicotines, respectively. The transfer of the alkylidene moiety of these complexes to nucleophilic olefins will be outlined and discussed. Especially relevant is the interaction of these pyridinium ylid complexes with unsaturated substrates such as dihydropyridines, enamines, and β-alkoxy bis(trimethyl-silyl) ketene acetals. This latter reaction leads to conjugated carboxylic acids, and has been be applied to a new synthesis of a honey bee pheromone, the queen substance.