9-hydroxy-5Z,7E,11Z,14Z-eicosatetraenoic acid

Base Information

• Chemical Name: 9-hydroxy-5Z,7E,11Z,14Z-eicosatetraenoic acid
• CAS No.: 79495-85-5
• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.472
• European Community (EC) Number: 632-823-1
• DSSTox Substance ID: DTXSID001347447
• Metabolomics Workbench ID: 2697
• Wikidata: Q27140147
• Mol file: 79495-85-5.mol

Synonyms:9-HETE;79495-85-5;9-hydroxy-5Z,7E,11Z,14Z-eicosatetraenoic acid;(5Z,7E,11Z,14Z)-9-hydroxyicosa-5,7,11,14-tetraenoic acid;(+/-)-9-HETE;5,7,11,14-Eicosatetraenoicacid, 9-hydroxy-, (5Z,7E,11Z,14Z)-;(+/-)-9-Hydroxy-(5Z,7E,11Z,14Z)-eicosatetraenoic acid;(+/-)9-HETE;70968-92-2;SCHEMBL7718113;CHEBI:72786;KATOYYZUTNAWSA-OIZRIKEUSA-N;(??)9-HETE;DTXSID001347447;LMFA03060089;MFCD00065824;AKOS040755337;HY-113943A;9-hydroxyeicosa-5,7,11,14-tetraenoic acid;CS-0138488;SR-01000946918;9-hydroxy-(5Z,7E,11Z,14Z)-icosatetraenoic acid;SR-01000946918-1;Q27140147;9-hydroxy-5(Z),7(E),11(Z),14(Z)-eicosatetraenoic acid;(5Z,7E,11Z,14Z)-9-Hydroxy-5,7,11,14-eicosatetraenoic acid;5,7,11,14-Eicosatetraenoic acid, 9-hydroxy-, (5Z,7E,11Z,14Z)-;(+/-)-9-Hydroxy-(5Z,7E,11Z,14Z)-eicosatetraenoic acid, ~100 mug/mL in ethanol, ~98%

Chemical Property of 9-hydroxy-5Z,7E,11Z,14Z-eicosatetraenoic acid

Chemical Property:

• Vapor Pressure: 1.48E-11mmHg at 25°C
• Refractive Index: 1.513
• Boiling Point: 487.7°C at 760 mmHg
• Flash Point: 262.8°C
• PSA: 57.53000
• Density: 0.984g/cm³
• 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:

98% ^*data from raw suppliers

(+/-)-9-HETE ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36-7

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC=CCC(C=CC=CCCCC(=O)O)O
• Isomeric SMILES: CCCCC/C=C\C/C=C\CC(/C=C/C=C\CCCC(=O)O)O
• Uses: (+/-)-9-HETE is a metabolite of arachidonic acid found to be a major product of lipid peroxidation in atherosclerotis.

Technology Process of 9-hydroxy-5Z,7E,11Z,14Z-eicosatetraenoic acid

There total 19 articles about 9-hydroxy-5Z,7E,11Z,14Z-eicosatetraenoic 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:

dodeca-3,6-diyn-1-ol (65090-68-8) → +/-9-HETE (70968-92-2,107656-13-3,79495-85-5,107656-14-4)

Guidance literature:

Multi-step reaction with 14 steps

1: paralleled the route described for diazo-ketone 6

2: 2

3: NaBH₄/CeCl₃ / propan-2-ol; H₂O / 0 °C

4: pyridine / -10 °C

5: imidazole / dimethylformamide / 0 °C

6: H₂ / Lindlar / hexane; pyridine

7: 80percent AcOH / tetrahydrofuran; H₂O

8: 95 percent / CBr₄(Ph₂PCH₂)2 / CH₂Cl₂ / 0 °C

9: 50 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -40 deg C to RT, overnight

10: DCC/py/TFA / benzene; dimethylsulfoxide / 16 h / Ambient temperature

11: NaClO₂ / 2-methyl-propan-2-ol; H₂O

13: 81 percent / n-Bu₄NF / tetrahydrofuran

14: LiOH / 1,2-dimethoxy-ethane; H₂O

With pyridine; 1H-imidazole; lithium hydroxide; sodium chlorite; sodium tetrahydroborate; cerium(III) chloride; CBr₄(Ph₂PCH₂)2; tetrabutyl ammonium fluoride; hydrogen; acetic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; dirhodium tetraacetate; Lindlar's catalyst; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; isopropyl alcohol; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4039(01)91141-4

Reference yield:

1-Diazo-trideca-4,7-diyn-2-one (89682-62-2) → +/-9-HETE (70968-92-2,107656-13-3,79495-85-5,107656-14-4)

Guidance literature:

Multi-step reaction with 13 steps

1: 2

2: NaBH₄/CeCl₃ / propan-2-ol; H₂O / 0 °C

3: pyridine / -10 °C

4: imidazole / dimethylformamide / 0 °C

5: H₂ / Lindlar / hexane; pyridine

6: 80percent AcOH / tetrahydrofuran; H₂O

7: 95 percent / CBr₄(Ph₂PCH₂)2 / CH₂Cl₂ / 0 °C

8: 50 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -40 deg C to RT, overnight

9: DCC/py/TFA / benzene; dimethylsulfoxide / 16 h / Ambient temperature

10: NaClO₂ / 2-methyl-propan-2-ol; H₂O

12: 81 percent / n-Bu₄NF / tetrahydrofuran

13: LiOH / 1,2-dimethoxy-ethane; H₂O

With pyridine; 1H-imidazole; lithium hydroxide; sodium chlorite; sodium tetrahydroborate; cerium(III) chloride; CBr₄(Ph₂PCH₂)2; tetrabutyl ammonium fluoride; hydrogen; acetic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; dirhodium tetraacetate; Lindlar's catalyst; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; isopropyl alcohol; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4039(01)91141-4

Reference yield:

(2Z,4E)-Heptadeca-2,4-diene-8,11-diyne-1,6-diol (89682-65-5) → +/-9-HETE (70968-92-2,107656-13-3,79495-85-5,107656-14-4)

Guidance literature:

Multi-step reaction with 11 steps

1: pyridine / -10 °C

2: imidazole / dimethylformamide / 0 °C

3: H₂ / Lindlar / hexane; pyridine

4: 80percent AcOH / tetrahydrofuran; H₂O

5: 95 percent / CBr₄(Ph₂PCH₂)2 / CH₂Cl₂ / 0 °C

6: 50 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -40 deg C to RT, overnight

7: DCC/py/TFA / benzene; dimethylsulfoxide / 16 h / Ambient temperature

8: NaClO₂ / 2-methyl-propan-2-ol; H₂O

10: 81 percent / n-Bu₄NF / tetrahydrofuran

11: LiOH / 1,2-dimethoxy-ethane; H₂O

With pyridine; 1H-imidazole; lithium hydroxide; sodium chlorite; CBr₄(Ph₂PCH₂)2; tetrabutyl ammonium fluoride; hydrogen; acetic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; Lindlar's catalyst; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4039(01)91141-4

upstream raw materials:

+/-9-HETE Me-ester

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

dodeca-3,6-diyn-1-ol

1-Diazo-trideca-4,7-diyn-2-one

Refernces

• 1、 Beavers, William N.,Serwa, Remigiusz,Shimozu, Yuki,Tallman, Keri A.,Vaught, Melissa,Dalvie, Esha D.,Marnett, Lawrence J.,Porter, Ned A.. "ω-alkynyl lipid surrogates for polyunsaturated fatty acids: Free radical and enzymatic oxidations". . p. 11529 - 11539. Retrieved 2014/10/15.
• 2、 Easton, Christopher J.,Robertson, Thomas A.,Pitt, Michael J.,Rathjen, Deborah A.,Ferrante, Antonio,Poulos, Alfred. "Oxidation of oxa and thia fatty acids and related compounds catalysed by 5- and 15-lipoxygenase". . p. 317 - 322. Retrieved 2007/10/03.