8S-hydroxy-5Z,9E,11Z,14Z,17Z-eicosapentaenoic acid

Base Information

Chemical Name:8S-hydroxy-5Z,9E,11Z,14Z,17Z-eicosapentaenoic acid
CAS No.:118492-81-2
Molecular Formula:C₂₀H₃₀O₃
Molecular Weight:318.456
Hs Code.:
DSSTox Substance ID:DTXSID001347673
Nikkaji Number:J1.063.345A
Wikidata:Q63395610
Metabolomics Workbench ID:2712
Mol file:118492-81-2.mol

Synonyms:118492-81-2;8(S)-HEPE;8S-hydroxy-5Z,9E,11Z,14Z,17Z-eicosapentaenoic acid;8S-HEPE;(5Z,8S,9E,11Z,14Z,17Z)-8-hydroxyicosa-5,9,11,14,17-pentaenoic acid;8-HEPE;5,9,11,14,17-Eicosapentaenoicacid, 8-hydroxy-, (5Z,8S,9E,11Z,14Z,17Z)-;LMFA03070003;SCHEMBL5928207;DTXSID001347673;AKOS040755652;PD021005;J-003764;Q63395610;(5Z,8S,9E,11Z,14Z,17Z)-8-Hydroxy-5,9,11,14,17-icosapentaenoic acid;8(S)-hydroxy-5(Z),9(E),11(Z),14(Z),17(Z)-eicosapentaenoic acid

Suppliers and Price of 8S-hydroxy-5Z,9E,11Z,14Z,17Z-eicosapentaenoic 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

Cayman Chemical
8(S)-HEPE ≥98%
100μg
$ 450.00

Cayman Chemical
8(S)-HEPE ≥98%
50μg
$ 238.00

Cayman Chemical
8(S)-HEPE ≥98%
25μg
$ 125.00

American Custom Chemicals Corporation
8S-HYDROXY-5Z,9E,11Z,14Z,17Z-EICOSAPENTAENOIC ACID 95.00%
5MG
$ 504.96

AHH
8S-Hydroxy-5Z,9E,11Z,14Z,17Z-eicosapentaenoicacid 98%
0.1g
$ 488.00

Total 8 raw suppliers

Chemical Property of 8S-hydroxy-5Z,9E,11Z,14Z,17Z-eicosapentaenoic acid

Chemical Property:

PSA：57.53000
LogP:4.96350
XLogP3:4.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:13
Exact Mass:318.21949481
Heavy Atom Count:23
Complexity:428

Purity/Quality:

98%min ^*data from raw suppliers

8(S)-HEPE ≥98% ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CCC=CCC=CCC=CC=CC(CC=CCCCC(=O)O)O
Isomeric SMILES:CC/C=C\C/C=C\C/C=C\C=C\[C@H](C/C=C\CCCC(=O)O)O

Technology Process of 8S-hydroxy-5Z,9E,11Z,14Z,17Z-eicosapentaenoic acid

There total 6 articles about 8S-hydroxy-5Z,9E,11Z,14Z,17Z-eicosapentaenoic 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: 90.0%

: (S,5Z,9E,11Z,14Z,17Z)-8-[(tert-butyldimethylsilyl)oxy]icosa-5,9,11,14,17-pentaenoic acid

: 118492-81-2
8(S)-hydroxy-(5Z,9E,11Z,14Z,17Z)-eicosapentaenoic acid

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; aq. phosphate buffer; at 20 ℃; for 4h; pH=5; Cooling with ice;
DOI:10.1055/s-0037-1611976

Reference yield:

: 53046-97-2,167820-65-7,53250-56-9
(Z,Z)-1-hydroxynona-3,6-diene

: 118492-81-2
8(S)-hydroxy-(5Z,9E,11Z,14Z,17Z)-eicosapentaenoic acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 3 h / 20 °C / Cooling with ice

2.1: acetonitrile / 4 h / Reflux

3.1: sodium hexamethyldisilazane / hexane; tetrahydrofuran / 1 h / -78 - 0 °C / Cooling with ice

3.2: 3 h / -78 - 0 °C

3.3: 23 h / 0 °C

4.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 0.42 h / -78 °C

4.2: 0.25 h / 0 °C

5.1: N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -90 - 0 °C / Cooling with ice

5.2: 3 h / 0 °C

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran; aq. phosphate buffer / 4 h / 20 °C / pH 5 / Cooling with ice

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; oxalyl dichloride; tetrabutyl ammonium fluoride; iodine; sodium hexamethyldisilazane; triphenylphosphine; In tetrahydrofuran; aq. phosphate buffer; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile;
DOI:10.1055/s-0037-1611976

Reference yield:

: 120379-74-0
(3Z,6Z)-1-iodo-3,6-nonadien

: 118492-81-2
8(S)-hydroxy-(5Z,9E,11Z,14Z,17Z)-eicosapentaenoic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: acetonitrile / 4 h / Reflux

2.1: sodium hexamethyldisilazane / hexane; tetrahydrofuran / 1 h / -78 - 0 °C / Cooling with ice

2.2: 3 h / -78 - 0 °C

2.3: 23 h / 0 °C

3.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 0.42 h / -78 °C

3.2: 0.25 h / 0 °C

4.1: N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -90 - 0 °C / Cooling with ice

4.2: 3 h / 0 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran; aq. phosphate buffer / 4 h / 20 °C / pH 5 / Cooling with ice

With N,N,N,N,N,N-hexamethylphosphoric triamide; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; In tetrahydrofuran; aq. phosphate buffer; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile;
DOI:10.1055/s-0037-1611976