64265-94-7

Basic information

• Product Name: 9-oxo-10,12,15-octadecatrienoic acid
• Synonyms: 9-oxo-10,12,15-octadecatrienoic acid;(10E,12Z,15Z)-9-hydroperoxyoctadeca-10,12,15-trienoic acid
• CAS NO: 64265-94-7
• Molecular Formula: C18H30O4
• Molecular Weight: 310.43
• Mol File: 64265-94-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 462°C at 760 mmHg
• Flash Point: 247.3°C
• Appearance: /
• Density: 0.98g/cm³
• Vapor Pressure: 8.11E-10mmHg at 25°C
• Refractive Index: 1.496
• PKA: 4.78±0.10(Predicted)
• CAS DataBase Reference: 9-oxo-10,12,15-octadecatrienoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 9-oxo-10,12,15-octadecatrienoic acid(64265-94-7)
• EPA Substance Registry System: 9-oxo-10,12,15-octadecatrienoic acid(64265-94-7)

Safety Data

• Hazardous Substances Data: 64265-94-7(Hazardous Substances Data)

Usage

Description

9-oxo-10,12,15-octadecatrienoic acid, also known as a lipid hydroperoxide, is a compound derived from (10E,12Z,15Z)-octadeca-10,12,15-trienoic acid by substituting a hydrogen at position 9 with a hydroperoxy group. This molecule is characterized by its unique structure and functional groups, which may contribute to its potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
9-oxo-10,12,15-octadecatrienoic acid is used as a pharmaceutical compound for its potential therapeutic properties. The hydroperoxy group in its structure may provide antioxidant or anti-inflammatory effects, which could be beneficial in the treatment of various diseases and conditions.
Used in Chemical Research:
In the field of chemical research, 9-oxo-10,12,15-octadecatrienoic acid can be utilized as a starting material or intermediate for the synthesis of more complex molecules with specific biological activities. Its unique structure and functional groups make it an interesting candidate for further exploration and development.
Used in Analytical Chemistry:
9-oxo-10,12,15-octadecatrienoic acid can be employed as a reference compound or standard in analytical chemistry for the identification and quantification of similar lipid hydroperoxides. Its distinct structure and properties can aid in the development of accurate and reliable analytical methods.
Used in Material Science:
The unique properties of 9-oxo-10,12,15-octadecatrienoic acid, such as its hydroperoxy group, may also find applications in material science. It could potentially be used in the development of new materials with specific properties, such as improved stability or reactivity, depending on the desired application.

InChI:InChI=1/C18H28O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h3-4,6,8,11,14H,2,5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b4-3+,8-6+,14-11+

Upstream product

• 463-40-1 (9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid 

Relevant articles and documents

Polyunsaturated C18 fatty acids derivatized with Gly and Ile as an additional tool for studies of the catalytic evolution of fungal 8- and 9-dioxygenases

The fungal linoleate diol synthase (LDS) family contains over twenty characterized 8-, 9-, and 10-dioxygenases (DOX), usually fused to catalytically competent cytochromes P450. Crystal structures are not available, but indirect evidence suggests that linoleic acid enters the active site of 8R-DOX-LDS headfirst and enters 9S-DOX-allene oxide synthase (AOS) with the ω-end (tail) first. Fatty acids derivatized with amino acids can conceivably be used to study oxidation in tail first position by enzymes, which bind natural fatty acids headfirst. The results might reveal catalytic similarities of homologous enzymes. 8R-DOX-5,8-LDS oxidize 18:2n-6-Ile and 18:2n-6-Gly in tail first position to 9S-hydroperoxy metabolites, albeit with less position and stereo specificity than 9S-DOX-AOS. The oxygenation mechanism of 9S-DOX-AOS with antarafacial hydrogen abstraction at C-11 and oxygen insertion at C-9 was also retained. Two homologues, 8R-DOX-7,8-LDS and 8R-DOX-AOS, oxidized 18:2n-6-Ile and 18:2n-6-Gly at C-9, suggesting a conserved feature of 8R-DOX domains. 9R-DOX-AOS, with 54% sequence identity to 9S-DOX-AOS, did not oxidize the derivatized C18 fatty acids. 9Z,12Z-16:2, two carbon shorter than 18:n-6 from the ω-end, was rapidly metabolized to an α-ketol, but 7Z,10Z-16:2 was not a substrate. An unsaturated carbon chain from C-1 to C-8 was apparently more important than the configuration at the ω-end. 8R-DOX-LDS and 9R-DOX-AOS may thus bind 18:2n-6 in the same orientation. The oxidation of 18:2n-6 in straight or reverse head-to-tail positions illustrates evolutionary traits between 8- and 9-DOX domains. Fatty acids derivatized with amino acids provide a complementary tool for the analysis of evolution of enzymes.

Physcomitrella patens has lipoxygenases for both eicosanoid and octadecanoid pathways

Mosses have substantial amounts of long chain C20 polyunsaturated fatty acids, such as arachidonic and eicosapentaenoic acid, in addition to the shorter chain C18 α-linolenic and linoleic acids, which are typical substrates of lipoxygenases in flowering p