12R-Hete

Base Information

• Chemical Name: 12R-Hete
• CAS No.: 82337-46-0
• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.472
• UNII: FD492J7LCU
• DSSTox Substance ID: DTXSID90333410
• Nikkaji Number: J260.110I
• Wikidata: Q27070762
• Pharos Ligand ID: R311KSH7TTMN
• Metabolomics Workbench ID: 2634
• ChEMBL ID: CHEMBL1435825
• Mol file: 82337-46-0.mol

Synonyms:12 S Hydroxyeicosatetraenoic Acid;12-HETE;12-Hydroxy-5,8,10,14-eicosatetraenoic Acid;12-R-HETE;12-S-HETE;12-S-Hydroxyeicosatetraenoic Acid;Acid, 12-S-Hydroxyeicosatetraenoic

Chemical Property of 12R-Hete

Chemical Property:

• PSA: 57.53000
• LogP: 5.18750
• Storage Temp.: -20°C
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 14
• Exact Mass: 320.23514488
• Heavy Atom Count: 23
• Complexity: 392

Purity/Quality:

99% ^*data from raw suppliers

12??R??-Hete 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 12R-Hete

There total 27 articles about 12R-Hete 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: 85.0%

(R)-methyl (5Z,8Z,10Z,14Z)-12-hydroxyeicosa-5,8,10,14-tetraenoate (100428-45-3) → (R)-12-HETE (82337-46-0)

Guidance literature:

With lithium hydroxide; carbon dioxide; In tetrahydrofuran; methanol; at 0 ℃; for 2.5h;

DOI:10.1016/S0040-4020(00)00983-2

Reference yield: 75.0%

Methyl (5Z,8Z,10E,12R,14Z)-12(tert-butyldiphenylsiloxy),5,8,10,14-icosatetraenoate (100428-44-2) → (R)-12-HETE (82337-46-0)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 25 ℃;

DOI:10.1055/s-1989-27425

Reference yield:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → 12-hydroxyeicosatetraenoic acid (54397-83-0,59985-28-3) + (R)-12-HETE (82337-46-0) + 8(S)-hydroxyeicosatetraenoic acid (98462-03-4,79495-84-4) + (8R)-hydroxyeicosatetraenoic acid (105500-09-2,79495-84-4) + (R)-11-hydroxy-eicosa-5,8,12,14-tetraenoic acid (73347-43-0,73804-65-6) + icomucret (54845-95-3,73945-47-8,83603-31-0) + 15(R)-HETE (73945-47-8,83603-31-0) + (S)-11-hydroxy-eicosa-5,8,12,14-tetraenoic acid (54886-50-9,73804-65-6)

Guidance literature:

all cis 5,8,11,14-eicosatetraenoic acid; With 8R-lipoxygenase A₅₈₉M mutant; sodium chloride; calcium chloride; In ethanol; at 20 ℃; pH=8; Enzymatic reaction;

With triphenylphosphine; In methanol; at 20 ℃; for 0.5h; Reagent/catalyst; Kinetics;

DOI:10.1074/jbc.M114.599662

upstream raw materials:

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

(R)-methyl (5Z,8Z,10Z,14Z)-12-hydroxyeicosa-5,8,10,14-tetraenoate

(5Z,8Z,10E)-(R)-12-(tert-Butyl-diphenyl-silanyloxy)-icosa-5,8,10-trien-14-ynoic acid methyl ester

Methyl (5Z,8Z,10E,12R,14Z)-12(tert-butyldiphenylsiloxy),5,8,10,14-icosatetraenoate

Refernces

• 1、 Neau, David B.,Bender, Gunes,Boeglin, William E.,Bartlett, Sue G.,Brash, Alan R.,Newcomer, Marcia E.. "Crystal structure of a lipoxygenase in complex with substrate: The arachidonic acid-binding site of 8R-lipoxygenase". . p. 31905 - 31913. Retrieved 2015/02/19.
• 2、 Rodríguez,Nomen,Spur,Godfroid,Lee. "Total synthesis of 12(R)-HETE, 12(S)-HETE, 2H2-12(R)-HETE and LTB4 from racemic glycidol via hydrolytic kinetic resolution". . p. 25 - 37. Retrieved 2007/10/03.