73347-43-0

Basic information

• Product Name: 11(R)-HETE
• Synonyms: 11R-HYDROXY-5Z,8Z,12E,14Z-EICOSATETRAENOIC ACID;11(R)-HETE;11(R)-hydroxy-(5Z,8Z,12E,14Z)-*eicosatetraenoic A;11(R)-HYDROXY-(5Z,8Z,12E,14Z)-*EICOSATET RAENOIC ACI;(5E,8Z,11R,12Z,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoic acid;GCZRCCHPLVMMJE-WXMXURGXSA-N
• CAS NO: 73347-43-0
• Molecular Formula: C20H32O3
• Molecular Weight: 320.47
• Mol File: 73347-43-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 487.7°C at 760 mmHg
• Flash Point: 14 °C
• Appearance: /
• Density: 0.984g/cm³
• Vapor Pressure: 1.48E-11mmHg at 25°C
• Refractive Index: 1.513
• Storage Temp.: -20°C
• CAS DataBase Reference: 11(R)-HETE(CAS DataBase Reference)
• NIST Chemistry Reference: 11(R)-HETE(73347-43-0)
• EPA Substance Registry System: 11(R)-HETE(73347-43-0)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 7-16
• Hazardous Substances Data: 73347-43-0(Hazardous Substances Data)

Usage

Definition

ChEBI: An optically active form of 11-HETE having 11(R)-configuration.

InChI:InChI=1/C20H32O3/c1-2-3-4-5-7-10-13-16-19(21)17-14-11-8-6-9-12-15-18-20(22)23/h6-7,9-11,13-14,16,19,21H,2-5,8,12,15,17-18H2,1H3,(H,22,23)/b9-6+,10-7-,14-11-,16-13-/t19-/m0/s1

Upstream product

• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 79060-22-3 1,2-O-isopropylidene-3E,5Z-undecadien-1,2R-diol 
• 79060-18-7 tert-Butyl-dimethyl-((2E,4Z)-(R)-1-prop-2-ynyl-deca-2,4-dienyloxy)-silane 
• 79060-17-6 methyl 5-bromo-5,6-heptadienoate 
• 79060-19-8 (5E,7Z)-(R)-Trideca-5,7-dien-1-yn-4-ol 
• 4757-80-6 (S,E)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)acrylaldehyde 
• 60106-53-8 n-hexyltriphenylphosphonium iodide 
• 79083-18-4 (5Z,8Z,12E,14Z)-(R)-11-Hydroxy-icosa-5,8,12,14-tetraenoic acid methyl ester 
• 79060-16-5 (12E,14Z)-(R)-11-(tert-Butyl-dimethyl-silanyloxy)-icosa-12,14-diene-5,8-diynoic acid methyl ester 
• 79060-15-4 (5Z,8Z,12E,14Z)-(R)-11-(tert-Butyl-dimethyl-silanyloxy)-icosa-5,8,12,14-tetraenoic acid methyl ester 

Relevant articles and documents

Stereospecific Total Synthesis of 11(R)-HETE (2), Lipoxygenation Product of Arachidonic Acid via the Prostaglandin Pathway

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Crystal structure of a lipoxygenase in complex with substrate: The arachidonic acid-binding site of 8R-lipoxygenase

Lipoxygenases (LOX) play critical roles in mammalian biology in the generation of potent lipid mediators of the inflammatory response; consequently, they are targets for the development of isoform-specific inhibitors. The regio- and stereo-specificity of the oxygenation of polyunsaturated fatty acids by the enzymes is understood in terms of the chemistry, but structural observation of the enzyme-substrate interactions is lacking. Although several LOX crystal structures are available, heretofore the rapid oxygenation of bound substrate has precluded capture of the enzyme-substrate complex, leaving a gap between chemical and structural insights. In this report, we describe the 2.0 ? resolution structure of 8R-LOX in complex with arachidonic acid obtained under anaerobic conditions. Subtle rearrangements, primarily in the side chains of three amino acids, allow binding of arachidonic acid in a catalytically competent conformation. Accompanying experimental work supports a model in which both substrate tethering and cavity depth contribute to positioning the appropriate carbon at the catalytic machinery.

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