100896-35-3

Basic information

• Product Name: 8-hydroperoxyeicosatetraenoic acid
• Synonyms: 8-hydroperoxyeicosatetraenoic acid
• CAS NO: 100896-35-3
• Molecular Formula: C20H32 O4
• Molecular Weight: 336.47
• Mol File: 100896-35-3.mol

Chemical Properties

• Boiling Point: 502.5°Cat760mmHg
• Flash Point: 169.1°C
• Appearance: /
• Density: 1.013g/cm³
• Vapor Pressure: 3.35E-12mmHg at 25°C
• Refractive Index: 1.512
• CAS DataBase Reference: 8-hydroperoxyeicosatetraenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 8-hydroperoxyeicosatetraenoic acid(100896-35-3)
• EPA Substance Registry System: 8-hydroperoxyeicosatetraenoic acid(100896-35-3)

Safety Data

• Hazardous Substances Data: 100896-35-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H32O4/c1-2-3-4-5-6-7-8-9-10-13-16-19(24-23)17-14-11-12-15-18-20(21)22/h6-7,9-11,13-14,16,19,23H,2-5,8,12,15,17-18H2,1H3,(H,21,22)/b7-6-,10-9-,14-11+,16-13-/t19-/m0/s1

Upstream product

• 96349-33-6 (5Z,8Z)-9-[2-Bromo-3-((Z)-oct-2-enyl)-cyclopropyl]-nona-5,8-dienoic acid 
• 96349-29-0 [2-Bromo-3-(5,5-dimethyl-[1,3]dioxan-2-yl)-cyclopropyl]-acetaldehyde 
• 96349-27-8 2-[2-Bromo-3-(5,5-dimethyl-[1,3]dioxan-2-yl)-cyclopropyl]-ethanol 
• 74765-98-3 2-[2-Bromo-3-((Z)-oct-2-enyl)-cyclopropyl]-5,5-dimethyl-[1,3]dioxane 
• 74766-00-0 2-Bromo-3-((Z)-oct-2-enyl)-cyclopropanecarbaldehyde 
• 4762-26-9 hexyltriphenylphosphonium bromide 
• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 96349-26-7 7-Bromo-2-ethoxy-3-oxa-bicyclo[4.1.0]heptane 

Downstream Products

• 13345-50-1 prostaglandin A₂ 

Relevant articles and documents

BIOSYNTHESIS OF 8-R-HPETE AND PRECLAVULONE-A FROM ARACHIDONATE IN SEVERAL SPECIES OF CARIBBEAN CORAL. A WIDESPREAD ROUTE TO MARINE PROSTANOIDS.

The Caribbean coral species Plexaura homomalla, Plexaura nina, Plexaura flexuosa, Pseudopterogorgia americana, Muriceopsis flavida, and Eunicea asperula have all been found to convert arachidonate to 8-R-HPETE (4) and preclavulone-A (3) demonstrating that this route to marine prostanoids is widespread among such coral.

General Synthesis of Polyunsaturated Fatty Acid Hydroperoxides Involving a Novel Vinylcyclopropyl Bromide Ring Opening

A variety of 18- and 20-carbon polyunsaturated fatty acid hydroperoxides were synthesized via an orbital symmetry controlled ring opening of vinylcyclopropyl bromides.Six 20-carbon vinylcyclopropyl bromides (20-25) were synthesized by a route starting from 2-ethoxy-Δ3,5-dihydropyran (3) and an 18-carbon vinylcyclopropyl bromide by a route starting from propargyl alcohol.All six vinylcyclopropyl bromides underwent facile Ag+-asisted ring opening in the presence of excess H2O2 to form the target fatty acid hydroperoxide isomers in good yields.In most cases the products were produced with stereochemical control.The product hydroperoxides formed in this ring-opening reaction are consistent with a mechanism involving the formation of a pentadienyl cation intermediate.A minor product found in the reaction of vinylcyclopropyl bromide 26 provides evidence that homoallylic participation by alkenyl substituents can change the course of the electrocyclic ring opening.

Unified Mechanism for Polyunsaturated Fatty Acid Autooxidation. Competition of Peroxy Radical Hydrogen Atom Abstraction, β-Scission, and Cyclization

The autooxidation of linoleic (18:2) and arachidonic (20:4) acids with several cosubstrates was investigated.Cumene, tetralin, 1,4-cyclohexadiene, and 9,10-dihydroanthracene in benzene were used as cosubstrates for the oxidation of linoleic acid.The distribution of products, trans,cis diene hydroperoxides and trans,trans diene hydroperoxides, was dependent on the ability of cosubstrates to donate hydrogen atoms to linoleate peroxy radicals.Arachidonic acid was oxidized in mixtures of benzene/1,4-cyclohexadiene with linoleic acid internal standard.Product distribution of six hydroperoxyeicosatetraenoic acids (HPETE) derived from arachidonic acid was established at different concentrations of 1,4-cyclohexadiene in the solvent mixture.A kinetic expression is derived that is useful in describing polyunsaturated fatty acid oxidation product mixtures.By the use of this kinetic derivation, the rate of cyclization of peroxy free radicals derived from arachidonic acid was determined.