8-Hydroxy-11,12-epoxyeicosa-5,9,14-trienoic acid

Base Information

Chemical Name:8-Hydroxy-11,12-epoxyeicosa-5,9,14-trienoic acid
CAS No.:85589-24-8
Deprecated CAS:96790-35-1
Molecular Formula:C₂₀H₃₂O₄
Molecular Weight:336.472
Hs Code.:
DSSTox Substance ID:DTXSID40950873
Nikkaji Number:J448.579C
Wikipedia:Hepoxilin
Wikidata:Q5731958
Mol file:85589-24-8.mol

Synonyms:8-EH-2;8-hydroxy-11,12-epoxyeicosa-5,9,14-trienoic acid;hepoxilin A;hepoxilin A3;hexophilin A3;HXA3 cpd

Suppliers and Price of 8-Hydroxy-11,12-epoxyeicosa-5,9,14-trienoic acid

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

TRC
HepoxilinA3(MixtureofDiastereomers)
25mg
$ 13750.00

TRC
HepoxilinA3(MixtureofDiastereomers)
10mg
$ 10725.00

Total 2 raw suppliers

Chemical Property of 8-Hydroxy-11,12-epoxyeicosa-5,9,14-trienoic acid

Chemical Property:

Vapor Pressure:2.28E-11mmHg at 25°C
Boiling Point:483.3°Cat760mmHg
Flash Point:162.4°C
PSA：70.06000
Density:1.078g/cm³
LogP:4.39870
XLogP3:4.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:14
Exact Mass:336.23005950
Heavy Atom Count:24
Complexity:425

Purity/Quality:

98%Min ^*data from raw suppliers

HepoxilinA3(MixtureofDiastereomers) ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CCCCCC=CCC1C(O1)C=CC(CC=CCCCC(=O)O)O
Isomeric SMILES:CCCCC/C=C/CC1C(O1)/C=C/C(C/C=C/CCCC(=O)O)O
Uses Hepoxilin A3, is nonclassic eicosanoid hormones involved in inflammation. They are appear to be pro-inflammatory in the skin, but hey are anti-inflammatory agents in human neutrophils. Hepoxilin A3, are potent insulin secretagogues. Hepoxilins are also produced in the brain, under oxidative stress.

Technology Process of 8-Hydroxy-11,12-epoxyeicosa-5,9,14-trienoic acid

There total 10 articles about 8-Hydroxy-11,12-epoxyeicosa-5,9,14-trienoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 96202-86-7
(5Z,9E)-10-[(2R,3R)-((Z)-3-Oct-2-enyl)-oxiranyl]-8-oxo-deca-5,9-dienoic acid methyl ester

: 607685-44-9,96790-35-1
8-hydroxy-11,12(S,S)-epoxyeicosa-5,14(Z),9(E)-trienoic acid

: 85589-24-8,94161-11-2,125226-84-8,125276-40-6,129171-41-1,129171-42-2,96790-35-1
8-hydroxy-11,12(S,S)-epoxyeicosa-5,14(Z),9(E)-trienoic acid

Guidance literature:: With sodium tetrahydroborate; In methanol; at -40 ℃; for 10h;
DOI:10.1016/S0040-4039(01)81539-2

Reference yield:

: 928-90-5
5-hexyl-1-ol

: 85589-24-8,94161-11-2,125226-84-8,125276-40-6,129171-41-1,129171-42-2,96790-35-1
8-hydroxy-11,12(S,S)-epoxyeicosa-5,14(Z),9(E)-trienoic acid

Guidance literature:: Multi-step reaction with 10 steps

1: 76 percent / Jones reagent / 0 °C

2: 1.) C₂H₅MgBr; 2.) CuBr / 1.) THF, 0 deg C; 2.) 0 deg C for 15 min, reflux for 8 h.

4: 89 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 4 h / 23 °C

5: 99 percent / H₂ / Lindlar / tetrahydrofuran / 0.75 h / 23 °C

6: 99 percent / potassium bromide / tetrahydrofuran; aq. acetic acid / 10 h / 0 °C

7: 92 percent / Jones reagens / 1.5 h / 23 °C

8: CHCl₃ / 3 h / Heating

9: 1.) 1N aq.NaOH / 1.) chloroform, 23 grad C, 3 min; 2). benzene, 23 grad C, 10 h.

10: NaBH₄ / methanol / 0.17 h / -40 °C

With sodium hydroxide; sodium tetrahydroborate; jones reagent; Jones Reagens; ethylmagnesium bromide; hydrogen; 3-chloro-benzenecarboperoxoic acid; potassium bromide; copper(I) bromide; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; chloroform; acetic acid;
DOI:10.1016/S0040-4039(01)81539-2

Reference yield:

: 53293-00-8
hex-5-ynoic acid

: 85589-24-8,94161-11-2,125226-84-8,125276-40-6,129171-41-1,129171-42-2,96790-35-1
8-hydroxy-11,12(S,S)-epoxyeicosa-5,14(Z),9(E)-trienoic acid

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) C₂H₅MgBr; 2.) CuBr / 1.) THF, 0 deg C; 2.) 0 deg C for 15 min, reflux for 8 h.

3: 89 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 4 h / 23 °C

4: 99 percent / H₂ / Lindlar / tetrahydrofuran / 0.75 h / 23 °C

5: 99 percent / potassium bromide / tetrahydrofuran; aq. acetic acid / 10 h / 0 °C

6: 92 percent / Jones reagens / 1.5 h / 23 °C

7: CHCl₃ / 3 h / Heating

8: 1.) 1N aq.NaOH / 1.) chloroform, 23 grad C, 3 min; 2). benzene, 23 grad C, 10 h.

9: NaBH₄ / methanol / 0.17 h / -40 °C

With sodium hydroxide; sodium tetrahydroborate; Jones Reagens; ethylmagnesium bromide; hydrogen; 3-chloro-benzenecarboperoxoic acid; potassium bromide; copper(I) bromide; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; chloroform; acetic acid;
DOI:10.1016/S0040-4039(01)81539-2