5,12,19-Trihydroxy-6,8,10,14-eicosatetraenoic acid

Base Information

• Chemical Name: 5,12,19-Trihydroxy-6,8,10,14-eicosatetraenoic acid
• CAS No.: 117605-61-5
• Molecular Formula: C₂₀H₃₂O₅
• Molecular Weight: 352.471
• Mol file: 117605-61-5.mol

Synonyms:19-hydroxy-LTB4;5,12,19-trihydroxy-6,8,10,14-eicosatetraenoic acid

Chemical Property of 5,12,19-Trihydroxy-6,8,10,14-eicosatetraenoic acid

Chemical Property:

• Vapor Pressure: 9.35E-16mmHg at 25°C
• Boiling Point: 577.8°Cat760mmHg
• Flash Point: 317.3°C
• PSA: 97.99000
• Density: 1.096g/cm³
• LogP: 3.12910
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 14
• Exact Mass: 352.22497412
• Heavy Atom Count: 25
• Complexity: 451

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 5,12,19-Trihydroxy-6,8,10,14-eicosatetraenoic acid

There total 28 articles about 5,12,19-Trihydroxy-6,8,10,14-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: 64.0%

ethyl 5(S),19(RS)-dibenzoyloxy-12(R)-hydroxy-icosa-6(Z),8(E),10(E),14(Z)-tetraenoate (134268-90-9,134679-37-1) → 5(S),12(R),19(RS)-trihydroxy-icosa-6(Z),8(E),10(E),14(Z)-tetraenoic acid (195061-89-3,117605-61-5)

Guidance literature:

With potassium carbonate; In methanol; water; for 120h; Ambient temperature;

Reference yield:

C7H10LiO(1-)*Li(1+) → 5(S),12(R),19(RS)-trihydroxy-icosa-6(Z),8(E),10(E),14(Z)-tetraenoic acid (195061-89-3,117605-61-5)

Guidance literature:

Multi-step reaction with 14 steps

1: 1.) HMPT / 1.) THF, 65 grad C, 6 h; 2.) 0 grad C, 0.5 h

2: 74 percent / H₂ / Lindlar cat. / benzene

3: 99 percent / TFA / H₂O / 1 h / 0 °C

4: 86 percent / Pb(OAc)4 / CH₂Cl₂ / 1.25 h / -10 °C

5: 1.) K₂CO₃; 2.) I₂ / 1.)THF, Et₂O, H₂O, 23 h; 2.)CH₂Cl₂, 6 h

6: 84 percent / CeCl₃, NaBH₄ / propan-2-ol / 3.5 h

7: 63 percent / K₂CO₃ / methanol / 4 h / 50 °C

8: 77 percent / (CH₃OPh)Ph₂CCl / pyridine / 0.03 h / 110 °C

9: 1.) Im_.; 2.) HCO₂H / 1.) DMF, 72 h; 2.) H₂O, THF, 1.5 h, 20 grad C

10: 100 percent / CBr₄, DIPHOS / CH₂Cl₂ / 0.83 h / -35 °C

11: 96 percent / acetonitrile / 2 h

12: 1.) BuLi; 2.) HMPT / 1.) THF, -100 grad C; 2.) -100 grad C to r.t.

13: nBu₄NF / tetrahydrofuran

14: K₂CO₃ / methanol

With lead(IV) acetate; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; formic acid; cerium(III) chloride; carbon tetrabromide; temephos; (CH₃OPh)Ph₂CCl; impramine; tetrabutyl ammonium fluoride; hydrogen; iodine; potassium carbonate; trifluoroacetic acid; Lindlar catalyst; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; isopropyl alcohol; acetonitrile; benzene;

DOI:10.1016/0040-4039(88)85249-3

Reference yield:

(4R,5R)-4,5-Bis-((R)-1,8-bis-benzyloxy-non-3-ynyl)-2,2-dimethyl-[1,3]dioxolane → 5(S),12(R),19(RS)-trihydroxy-icosa-6(Z),8(E),10(E),14(Z)-tetraenoic acid (195061-89-3,117605-61-5)

Guidance literature:

Multi-step reaction with 13 steps

1: 74 percent / H₂ / Lindlar cat. / benzene

2: 99 percent / TFA / H₂O / 1 h / 0 °C

3: 86 percent / Pb(OAc)4 / CH₂Cl₂ / 1.25 h / -10 °C

4: 1.) K₂CO₃; 2.) I₂ / 1.)THF, Et₂O, H₂O, 23 h; 2.)CH₂Cl₂, 6 h

5: 84 percent / CeCl₃, NaBH₄ / propan-2-ol / 3.5 h

6: 63 percent / K₂CO₃ / methanol / 4 h / 50 °C

7: 77 percent / (CH₃OPh)Ph₂CCl / pyridine / 0.03 h / 110 °C

8: 1.) Im_.; 2.) HCO₂H / 1.) DMF, 72 h; 2.) H₂O, THF, 1.5 h, 20 grad C

9: 100 percent / CBr₄, DIPHOS / CH₂Cl₂ / 0.83 h / -35 °C

10: 96 percent / acetonitrile / 2 h

11: 1.) BuLi; 2.) HMPT / 1.) THF, -100 grad C; 2.) -100 grad C to r.t.

12: nBu₄NF / tetrahydrofuran

13: K₂CO₃ / methanol

With lead(IV) acetate; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; formic acid; cerium(III) chloride; carbon tetrabromide; temephos; (CH₃OPh)Ph₂CCl; impramine; tetrabutyl ammonium fluoride; hydrogen; iodine; potassium carbonate; trifluoroacetic acid; Lindlar catalyst; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; isopropyl alcohol; acetonitrile; benzene;

DOI:10.1016/0040-4039(88)85249-3

upstream raw materials:

ethyl 5(S),19(RS)-dibenzoyloxy-12(R)-hydroxy-icosa-6(Z),8(E),10(E),14(Z)-tetraenoate

Refernces

• 1、 Le Merrer,Bonnet,Depezay. "Synthesis of 19-hydroxy LTB4, an assumed metabolite of leukotriene B4". . p. 2647 - 2650. Retrieved 2007/10/02.