7,8,17-Trihydroxydocosa-4,9,11,13,15,19-hexaenoic acid

Base Information

• Chemical Name: 7,8,17-Trihydroxydocosa-4,9,11,13,15,19-hexaenoic acid
• CAS No.: 872993-05-0
• Molecular Formula: C22H32O5
• Molecular Weight: 376.493
• DSSTox Substance ID: DTXSID60694000
• NCI Thesaurus Code: C175295
• Mol file: 872993-05-0.mol

Synonyms:7,8,17-trihydroxy-4,9,11,13,15,19-docosahexaenoic acid;aspirin-triggered resolvin D1;AT-RvD1;resolvin D1;RvD1 fatty acid

Chemical Property of 7,8,17-Trihydroxydocosa-4,9,11,13,15,19-hexaenoic acid

Chemical Property:

• PSA: 97.99000
• LogP: 3.46130
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 14
• Exact Mass: 376.22497412
• Heavy Atom Count: 27
• Complexity: 555

Purity/Quality:

99% ^*data from raw suppliers

ResolvinD1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC(C=CC=CC=CC=CC(C(CC=CCCC(=O)O)O)O)O
• Uses: Resolvin D1 is used to protect against hepatic injury and heart failure, specifically in rats. Also used as a means to attenuate the inflammatory reaction.

Technology Process of 7,8,17-Trihydroxydocosa-4,9,11,13,15,19-hexaenoic acid

There total 32 articles about 7,8,17-Trihydroxydocosa-4,9,11,13,15,19-hexaenoic 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: 94.0%

methyl (4Z,7S,8R,9E,11E,13Z,15E,17S,19Z)-7,8,17-trihydroxydocosa-4,9,11,13,15,19-hexaenoate (937738-63-1,937738-64-2) → Resolvin D1 (872993-05-0,528583-91-7)

Guidance literature:

methyl (4Z,7S,8R,9E,11E,13Z,15E,17S,19Z)-7,8,17-trihydroxydocosa-4,9,11,13,15,19-hexaenoate; With water; lithium hydroxide; In methanol; at 0 ℃; Inert atmosphere;

With sodium dihydrogenphosphate; In ethyl acetate; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.10.059

Reference yield:

methyl (4Z,7S,8R,9E,11E,15E,17S,19Z)-7,8,17-trihydroxydocosa-4,9,11,15,19-pentaen-13-ynoate (1415668-79-9) → Resolvin D1 (872993-05-0,528583-91-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: water / methanol / 5 h / 50 °C

2.1: water; lithium hydroxide / methanol / 0 °C / Inert atmosphere

2.2: Inert atmosphere

With water; lithium hydroxide; In methanol;

DOI:10.1016/j.tetlet.2012.10.059

Reference yield:

(S)-3-[(tert-butyldiphenylsilyl)oxy]-1-[(2S,3S)-3-[2-((4-methoxybenzyl)oxy)ethyl]oxiran-2-yl]propan-1-ol → Resolvin D1 (872993-05-0,528583-91-7)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 20 °C

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / aq. phosphate buffer; dichloromethane / 2 h / 20 °C / pH 6.8

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.25 h / -78 °C

3.2: 0.17 h / -78 - 20 °C

4.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 20 °C

5.1: n-butyllithium; diisopropylamine / diethyl ether; hexane; tetrahydrofuran / 0.25 h / -78 °C

5.2: 0.25 h / -78 - 20 °C

6.1: zirconocene dichloride; diisobutylaluminium hydride / hexane; tetrahydrofuran / 1 h / -78 - 20 °C

6.2: 0.33 h / -78 - 20 °C

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

8.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 0 °C

9.1: pyridinium p-toluenesulfonate; methanol / dichloromethane / 3 h / 20 °C

10.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.25 h / -78 °C

10.2: 0.08 h / -78 - 20 °C

11.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 20 °C

11.2: 0.08 h / -78 - 0 °C

12.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide; tert-butylamine / 0.25 h / 20 °C

13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Cooling with ice

14.1: zinc; copper diacetate; silver nitrate / diethyl ether; water; methanol; acetone / 5 h / 20 °C

15.1: methanol; lithium hydroxide / water; tetrahydrofuran / 5 h / 20 °C

With 2,6-dimethylpyridine; methanol; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; zirconocene dichloride; oxalyl dichloride; tetrabutyl ammonium fluoride; copper diacetate; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; silver nitrate; dimethyl sulfoxide; tert-butylamine; diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hydroxide; zinc; In tetrahydrofuran; methanol; aq. phosphate buffer; diethyl ether; hexane; dichloromethane; water; acetone; 3.1: |Swern Oxidation / 3.2: |Swern Oxidation / 10.1: |Swern Oxidation / 10.2: |Swern Oxidation / 12.1: |Sonogashira Cross-Coupling;

DOI:10.1039/C8OB03128B

upstream raw materials:

[(4R,5S)-2,2-Dimethyl-5-((Z)-pent-2-enyl)-[1,3]dioxolan-4-yl]-methanol

C₁₁H₁₉IO₂

(3S,1E,5Z)-1-iodoocta-1,5-diene-3-ol

C₁₃H₂₂O₅

Refernces

• 1、 Rodriguez, Ana R.,Spur, Bernd W.. "Total synthesis of Resolvin D1, a potent anti-inflammatory lipid mediator". . p. 6990 - 6994. Retrieved 2013/01/15.