334-20-3

Basic information

• Product Name: (E)-9-Oxo-2-decenoic acid
• Synonyms: (E)-9-Oxo-2-decenoic acid;Queen substance;2-Decenoic acid, 9-oxo-, (E)-;Ai3-50125
• CAS NO: 334-20-3
• Molecular Formula: C₁₀H₁₆O₃
• Molecular Weight: 184.2322
• Mol File: 334-20-3.mol
• Article Data: 22

Chemical Properties

• Melting Point: 54.5-55.5°
• Boiling Point: 369.7°Cat760mmHg
• Flash Point: 191.6°C
• Appearance: /
• Density: 1.029g/cm³
• Vapor Pressure: 1.77E-06mmHg at 25°C
• Refractive Index: 1.471
• CAS DataBase Reference: (E)-9-Oxo-2-decenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-9-Oxo-2-decenoic acid(334-20-3)
• EPA Substance Registry System: (E)-9-Oxo-2-decenoic acid(334-20-3)

Safety Data

• Hazardous Substances Data: 334-20-3(Hazardous Substances Data)

Usage

Uses

Used in Cardiovascular Health:
(E)-9-Oxo-2-decenoic acid is used as a dietary supplement for improving cardiovascular health. Its consumption has been associated with reduced risk of heart diseases due to its ability to lower cholesterol levels and improve blood circulation.
Used in Anti-inflammatory Applications:
(E)-9-Oxo-2-decenoic acid is used as an anti-inflammatory agent for managing conditions such as arthritis and dermatitis. Its anti-inflammatory properties help alleviate pain, swelling, and inflammation associated with these conditions.
Used in Antioxidant Therapy:
(E)-9-Oxo-2-decenoic acid is used as an antioxidant to protect the body from oxidative stress and damage caused by free radicals. Its antioxidant properties help neutralize harmful substances and prevent cellular damage, thereby promoting overall health and well-being.
Used in Cancer Prevention and Treatment:
(E)-9-Oxo-2-decenoic acid is used as a chemopreventive and therapeutic agent for various types of cancer. Its anti-cancer properties have been shown to inhibit tumor growth, induce apoptosis, and modulate signaling pathways involved in cancer progression.
Used in Pharmaceutical Industry:
(E)-9-Oxo-2-decenoic acid is used as an active pharmaceutical ingredient in the development of drugs targeting various health conditions, including cardiovascular diseases, inflammatory disorders, and cancer.
However, it is important to note that excessive consumption of (E)-9-Oxo-2-decenoic acid has been linked to an increased risk of chronic diseases such as obesity and diabetes. Therefore, it is essential to maintain a balanced intake of both omega-6 and omega-3 fatty acids for optimal health.

InChI:InChI=1/C10H16O3/c1-9(11)7-5-3-2-4-6-8-10(12)13/h6,8H,2-5,7H2,1H3,(H,12,13)/b8-6+

Upstream product

• 141-82-2 malonic acid 
• 36219-80-4 7-oxo-octanal 
• 2575-06-6 Decen-(2^c+t)-on-⁽⁹⁾-saeure-⁽¹⁾-methylester 
• 3695-28-1 5-iodo-2-pentanone ethylene ketal 
• 64196-68-5 (Z)-4-acetoxy-2-buten-1-ol 
• 96181-65-6 Decen-(2^c+t)-on-⁽⁹⁾-saeure-⁽¹⁾-aethylenketal 
• 132806-71-4 (E)-8-[1,3]Dithian-2-yl-oct-2-enoic acid ethyl ester 
• 21573-31-9 oct-7-enal 
• 13103-40-7 rac-2-(tetrahydro-2H-pyran-2-yl)acetic acid 
• 3907-42-4 methyl 7-oxo-hept-2-enoate 
• 1189-65-7 Decadien-(2.7)-on-⁽⁹⁾-saeure-⁽¹⁾-methylester 
• 1190-99-4 Decen-⁽²⁾-in-⁽⁹⁾-ol-⁽⁷⁾-saeure-⁽¹⁾-methylester 
• 4224-70-8 6-bromohexanoic acid 
• 50775-02-5 7-bromo-2-heptanone 

Downstream Products

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

Relevant articles and documents

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.

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].

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 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).

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.

A simple and facile microwave assisted synthesis of 9-oxo-2(E)-decenoic acid

Synthesis of 9-oxo-2(E)-decenoic acid 1, the queen bee substance of Apis Mellifera, is reported utilizing microwave radiation in assisting the alkylation / decarboxylation and Knoevenagel condensation reactions.

Aleuritic acid in the preparation of (Z)-9-octadecene-1,18-dioic acid (intermediate in civetone synthesis) and queen substance of honey-bee utilizing phosphonate carbanions

Wittig-Horner-Emmons olefination on aldehydes derived from aleuritic acid leading to the formation of both pure Z and E isomers of 9-octadecene-1,18 dioic acid, in good yield (valuable intermediate for musk perfume civetone) and a synthesis of 9-oxo-(E)-2-decenoic acid (queen bee substance) are reported.

Synthesis of (E)-9-oxo-2-decenoic acid and (E)-10-hydroxy-2-decenoic acid

Syntheses of (E)-9-oxo-decenoic acid (III), queen's substance and (E)-10-hydroxy-2-decenoic acid (V), a componenet of royal jelly and a bee pheromone, have been accomplished through a common intermediate (I).