(9Z,11E,13S)-13-hydroxyoctadeca-9,11-dienoic acid

Base Information

• Chemical Name: (9Z,11E,13S)-13-hydroxyoctadeca-9,11-dienoic acid
• CAS No.: 29623-28-7
• Deprecated CAS: 148555-75-3
• Molecular Formula: C18H32 O3
• Molecular Weight: 296.45
• Hs Code.: 2918199090
• UNII: U2DA27TT5J,53CYY2A5PM
• DSSTox Substance ID: DTXSID201017286
• Nikkaji Number: J425.680H
• Wikipedia: 13-Hydroxyoctadecadienoic_acid
• Wikidata: Q21099640
• NCI Thesaurus Code: C131741
• Metabolomics Workbench ID: 2264
• ChEMBL ID: CHEMBL451721
• Mol file: 29623-28-7.mol

Synonyms:13-HODD;13-HODE;13-hydroxy-9,11-octadecadienoic acid;13-hydroxy-9,11-octadecadienoic acid, (E,E)-isomer;13-hydroxy-9,11-octadecadienoic acid, (E,Z)-isomer;13-hydroxy-9,11-octadecadienoic acid, (R)-(E,Z)-isomer;13-hydroxy-9,11-octadecadienoic acid, (S)-(E,Z)-isomer;13-hydroxy-9,11-octadecadienoic acid, (Z,E)-isomer;13-hydroxyoctadecadienoic acid;13-LOX

Chemical Property of (9Z,11E,13S)-13-hydroxyoctadeca-9,11-dienoic acid

Chemical Property:

• Boiling Point: 422.7°Cat760mmHg
• Flash Point: 223.6°C
• PSA: 57.53000
• Density: 0.97g/cm³
• LogP: 4.85530
• Storage Temp.: −20°C
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 14
• Exact Mass: 296.23514488
• Heavy Atom Count: 21
• Complexity: 295

Purity/Quality:

99% ^*data from raw suppliers

13(S)-HODE ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F
• Statements: 11
• Safety Statements: 7-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC=CCCCCCCCC(=O)O)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/C=C\CCCCCCCC(=O)O)O
• Uses: 13(S)-HODE is an inhibitor of tumor cell adhesion in endothelium tissue. 13(S)-HODE is also used to activate GPR132 which may affect autoimmune function and lymph organ size.

Technology Process of (9Z,11E,13S)-13-hydroxyoctadeca-9,11-dienoic acid

There total 73 articles about (9Z,11E,13S)-13-hydroxyoctadeca-9,11-dienoic 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: 100.0%

methyl coriolate (6410-93-1,10075-08-8,10219-70-2,23324-72-3,24058-13-7,26474-38-4,28392-55-4,57884-99-8,96393-37-2,114297-07-3,109837-85-6) → (R,S)-coriolic acid (10219-69-9,29623-28-7,29899-88-5,32819-31-1,73804-64-5,81445-95-6,114297-05-1,114818-04-1,114818-05-2,127911-29-9,128821-19-2,5204-88-6,149341-86-6,18104-45-5)

Guidance literature:

With lithium hydroxide; In water; isopropyl alcohol; for 1.5h; Ambient temperature;

Reference yield: 95.0%

(E)-13-hydroxyoctadec-9-yn-11-enoic acid (105857-40-7) → (R,S)-coriolic acid (10219-69-9,29623-28-7,29899-88-5,32819-31-1,73804-64-5,81445-95-6,114297-05-1,114818-04-1,114818-05-2,127911-29-9,128821-19-2,5204-88-6,149341-86-6,18104-45-5)

Guidance literature:

With quinoline; hydrogen; palladium on calcium fluoride poisoned with lead; In ethanol; under 760 Torr;

DOI:10.1021/jo00372a011

Reference yield: 94.0%

(9Z,11E)-13-hydroperoxyoctadeca-9,11-dienoic acid (5502-90-9,7324-21-2,28529-44-4,33964-75-9,40878-62-4,63121-48-2,73036-16-5,90760-91-1,90760-92-2,97672-38-3,104832-62-4,123410-62-8,126873-57-2,23017-93-8,18320-18-8) → (R,S)-coriolic acid (10219-69-9,29623-28-7,29899-88-5,32819-31-1,73804-64-5,81445-95-6,114297-05-1,114818-04-1,114818-05-2,127911-29-9,128821-19-2,5204-88-6,149341-86-6,18104-45-5)

Guidance literature:

With sodium tetrahydroborate; In methanol; for 0.166667h; Ambient temperature;

DOI:10.1248/cpb.41.1863

upstream raw materials:

12-13-monoepoxy-9-octadecenoic acid

linoleic acid

methyl coriolate

(9Z,11E)-13-hydroperoxyoctadeca-9,11-dienoic acid

Downstream raw materials:

methyl coriolate

(R)-δ-decalactone

(S)-(-)-tetrahydro-6-pentyl-2H-pyran-2-one

(10E)-9-hydroxy-13-oxo-10-octadecenoic acid

Refernces

• 1、 Hershelman, Dillon,Kahler, Kirsten M.,Price, Morgan J.,Lu, Iris,Fu,Plumeri, Patricia A.,Karaisz, Fred,Bassett, Natasha F.,Findeis, Peter M.,Clapp, Charles H.. "Oxygenation reactions catalyzed by the F557V mutant of soybean lipoxygenase-1: Evidence for two orientations of substrate binding". . . Retrieved 2019/09/10.
• 2、 Grechkin, Alexander N.,Ogorodnikova, Anna V.,Egorova, Alevtina M.,Mukhitova, Fakhima K.,Ilyina, Tatiana M.,Khairutdinov, Bulat I.. "Allene Oxide Synthase Pathway in Cereal Roots: Detection of Novel Oxylipin Graminoxins". . p. 336 - 343. Retrieved 2018/06/04.