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

Description

(E)-9-Oxo-2-decenoic acid, also known as linoleic acid, is a significant unsaturated omega-6 fatty acid predominantly found in plants and animals. It is a key constituent of various vegetable oils such as sunflower, safflower, and corn oil. Linoleic acid plays a crucial role in lipid metabolism and serves as an essential precursor for the synthesis of other fatty acids and prostaglandins. It exhibits anti-inflammatory, anti-cancer, and antioxidant properties, making it a vital component for maintaining overall health.

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

• 96181-65-6 Decen-(2^c+t)-on-⁽⁹⁾-saeure-⁽¹⁾-aethylenketal 
• 141-82-2 malonic acid 
• 36219-80-4 7-oxo-octanal 
• 872-01-5 trans-Nonen-8-in-carbonsaeure, Dec-9-in-trans-2-ensaeure 
• 57221-88-2 ethyl 9-oxo-trans-2-decenoate 
• 62026-31-7 [3-(2-methyl-[1,3]dioxolan-2-yl)-propyl]-magnesium chloride 
• 54002-57-2 methyl 2-methylthio-9-oxodecanoate 
• 3664-60-6 7-octene-2-one 
• 2695-47-8 6-Bromo-1-hexene 
• 5009-32-5 non-8-en-2-one 
• 132806-71-4 (E)-8-[1,3]Dithian-2-yl-oct-2-enoic acid ethyl ester 
• 171019-45-7 ethyl (2E)-9-formyloctenoate 
• 171019-44-6 ethyl 9-hydroxy-(E)-2-nonenoate 
• 78633-20-2 6-[1,3]Dithian-2-yl-hexanal 

Downstream Products

• 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 
• 91882-58-5 9-hydroxy-(E)-2-decenoic acid 
• 83944-98-3 (S,E)-(+)-9-hydroxydec-2E-enoic acid 
• 1189-64-6 (E)-9-Oxo-2-decanoic acid methyl ester 

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.

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).