9(S)-Hete

Base Information

• Chemical Name: 9(S)-Hete
• CAS No.: 107656-13-3
• Molecular Formula: C20H32O3
• Molecular Weight: 320.47
• DSSTox Substance ID: DTXSID801185384
• Nikkaji Number: J852.254E
• Wikidata: Q27116108
• Metabolomics Workbench ID: 2648
• Mol file: 107656-13-3.mol

Synonyms:9(S)-HETE;107656-13-3;9S-HETE;(5Z,7E,9S,11Z,14Z)-9-hydroxyicosa-5,7,11,14-tetraenoic acid;9S-hydroxy-5Z,7E,11Z,14Z-eicosatetraenoic acid;(5Z,7E,11Z,14Z)-(9S)-9-Hydroxyeicosa-5,7,11,14-tetraenoic acid;(5Z,7E,11Z,14Z)-(9S)-9-Hydroxyicosa-5,7,11,14-tetraenoic acid;BML1-B05;CHEBI:34495;9(S)-hydroxyeicosatetraenoic acid;DTXSID801185384;LMFA03060027;AKOS040755806;NCGC00161239-01;PD020975;SR-01000946920;J-001994;SR-01000946920-1;Q27116108;(S)-(Z,E,Z,Z)-9-hydroxyeicosa-5,7,11,14-tetraenoic acid;(S)-(Z,E,Z,Z)-9-hydroxyicosa-5,7,11,14-tetraenoic acid;9(S)-hydroxy-5(Z),7(E),11(Z),14(Z)-eicosatetraenoic acid;(5Z,7E,9S,11Z,14Z)-9-Hydroxy-5,7,11,14-eicosatetraenoic acid;(5Z,7E,9S,11Z,14Z)-9-hydroxyeicosa-5,7,11,14-tetraenoic acid

Chemical Property of 9(S)-Hete

Chemical Property:

• Vapor Pressure: 1.48E-11mmHg at 25°C
• Boiling Point: 487.7°C at 760 mmHg
• PKA: 4.73±0.10(Predicted)
• Flash Point: 262.8°C
• PSA: 57.53000
• Density: 0.984g/cm³
• LogP: 5.18750
• 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

9(S)-HETE ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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\C[C@@H](/C=C/C=C\CCCC(=O)O)O

Technology Process of 9(S)-Hete

There total 17 articles about 9(S)-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:

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、 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 2001.
• 2、 Adams, Julian,Rokach, Joshua. "SYNTHESIS OF +/- 8- and 9-HETES". . p. 35 - 38. Retrieved 2007/10/02.