15(S)-Hpete

Base Information

• Chemical Name: 15(S)-Hpete
• CAS No.: 70981-96-3
• Molecular Formula: C20H32 O4
• Molecular Weight: 336.4657
• UNII: 7BN3O939P6
• ChEMBL ID: CHEMBL1606580
• DSSTox Substance ID: DTXSID301318203
• Metabolomics Workbench ID: 2640
• Nikkaji Number: J461.011C
• Wikidata: Q27070784
• Mol file: 70981-96-3.mol

Synonyms:14,15-epoxyarachidonic acid;15-HPAA;15-HPEA;15-HPETE;15-hydroperoxy-5,8,11,13-eicosatetraenoic acid;15-hydroperoxy-5,8,11,13-eicosatetraenoic acid, (E,Z,Z,Z)-isomer;15-hydroperoxy-5,8,11,13-eicosatetraenoic acid, (S)-(E,Z,Z,Z)-isomer;15-hydroperoxy-5,8,11,13-eicosatetraenoic acid, (Z,Z,Z,Z)-isomer;15-hydroperoxy-5,8,11,14-eicosatetraenoic acid;15-hydroperoxyarachidonic acid;arachidonic acid 15-hydroperoxide

Chemical Property of 15(S)-Hpete

Chemical Property:

• Vapor Pressure: 6.75E-13mmHg at 25°C
• Boiling Point: 518 °C at 760 mmHg
• Flash Point: 175.6 °C
• PSA: 66.76000
• Density: 1.013 g/cm³
• LogP: 5.68480
• Storage Temp.: ?70°C
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 15
• Exact Mass: 336.23005950
• Heavy Atom Count: 24
• Complexity: 408

Purity/Quality:

99% ^*data from raw suppliers

15(S)-HPETE ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 11
• Safety Statements: 7-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC(C=CC=CCC=CCC=CCCCC(=O)O)OO
• Isomeric SMILES: CCCCC[C@@H](/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O)OO
• Uses: 15(S)-HpETE is a monohydroperoxy polyunsaturated fatty acid (PUFA) produced by the action of 15-lipoxygenase (15-LO) on arachidonic acid. It is either metabolized to 14,15-leukotriene A4 or reduced to 15(S)-HETE by peroxidases. 15(S)-HpETE mediates a number of biological functions including the induction of c-fos and c-jun, and activation of AP-1. 15(S)-HpETE inhibits prostacyclin synthesis in porcine aortic microsomes and bovine endothelial cells, and can cause the suicide inactivation of porcine 12-LO. 15(S)-HPETE is a primary metabolite of arachidonic acid shown to inhibit arachidonic acid induced platelet aggregation.

Technology Process of 15(S)-Hpete

There total 8 articles about 15(S)-Hpete 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: 92.0%

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → (5Z,8Z,11Z,13E)-15(S)-hydroperoxyeicosa-5,8,11,13-tetraenoic acid (70981-96-3)

Guidance literature:

With ammonium sulfate; soybean lipoxygenase;

DOI:10.1021/jm00385a005

Reference yield: 82.0%

methyl 15(S)-hydroperoxy-5(Z),8(Z),11(Z),13(E)-eicosatetraenoate (77026-90-5) → (5Z,8Z,11Z,13E)-15(S)-hydroperoxyeicosa-5,8,11,13-tetraenoic acid (70981-96-3)

Guidance literature:

With lithium hydroxide; 2,6-di-tert-butyl-4-methyl-phenol; dihydrogen peroxide; In tetrahydrofuran; water; 1.) 0 deg C, 10 min, 2.) r.t., 1 day;

DOI:10.1021/jo00106a037

Reference yield:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → (5Z,8Z,11Z,13E)-15(S)-hydroperoxyeicosa-5,8,11,13-tetraenoic acid (70981-96-3) + icomucret (54845-95-3,73945-47-8,83603-31-0)

Guidance literature:

With soybean lipoxygenase type I-B; at 20 ℃; pH=7.4; pH-value; Enzymatic reaction;

DOI:10.1016/j.chemphyslip.2014.09.005

upstream raw materials:

all cis 5,8,11,14-eicosatetraenoic acid

methyl 15(S)-hydroperoxy-5(Z),8(Z),11(Z),13(E)-eicosatetraenoate

15(S)-[(1-methoxy-1-methylethyl)dioxy]-5(Z),8(Z),11(Z),13(E)-eicosatetraenoic acid

methyl 15(S)-[(1-methoxy-1-methylethyl)dioxy]-5(Z),8(Z),11(Z),13(E)-eicosatetraenoate

Downstream raw materials:

13(R)-hydroxy-14(S),15(S)-epoxy-5(Z),8(Z),11(Z)-eicosatrienoic acid

8(R),15(S),5Z,9,11,13E-diHETE

8(S),15(S),5Z,9,11,13E-diHETE

(5Z,8Z,11Z,13E)-15-oxo-5,8,11,13-eicosatetraenoic acid

Refernces

• 1、 Boonprab, Kangsadan,Matsui, Kenji,Akakabe, Yoshihiko,Yotsukura, Norishige,Kajiwara, Tadahiko. "Hydroperoxy-arachidonic acid mediated n-hexanal and (Z)-3- and (E)-2-nonenal formation in Laminaria angustata". . p. 669 - 678. Retrieved 2003.
• 2、 Harrison, Paul,Jackson, Mark,Jones, Shaun,Kronig, Christel,Lennon, Ian C.,Simmonds, Shaun,Conrow, Raymond E.. "Manufacture of (5Z,8Z,11Z,13E)(15S)-15-hydroxyeicosa-5,8,11,13-tetraenoic acid sodium salt for clinical trials". experimental part. p. 301 - 304. Retrieved 2011/09/20.
• 3、 Jacquot, Cyril,McGinley, Chris M.,Plata, Erik,Holman, Theodore R.,Van Der Donk, Wilfred A.. "Synthesis of 11-thialinoleic acid and 14-thialinoleic acid, inhibitors of soybean and human lipoxygenases". supporting information; experimental part. p. 4242 - 4252. Retrieved 2009/02/07.