10-hydroxy-10-[(2S,3S)-3-oct-2-enyloxiran-2-yl]deca-5,8-dienoic acid

Base Information

• Chemical Name: 10-hydroxy-10-[(2S,3S)-3-oct-2-enyloxiran-2-yl]deca-5,8-dienoic acid
• CAS No.: 94161-10-1
• Molecular Formula: C₂₀H₃₂O₄
• Molecular Weight: 336.472
• DSSTox Substance ID: DTXSID70390602
• Mol file: 94161-10-1.mol

Synonyms:10-hydroxy-11,12-epoxyeicosa-5,8,14-trienoic acid;EPHETA;erythro-hepoxilin B3;hepoxilin B;hepoxilin B3;threo-hepoxilin B3

Chemical Property of 10-hydroxy-10-[(2S,3S)-3-oct-2-enyloxiran-2-yl]deca-5,8-dienoic acid

Chemical Property:

• Boiling Point: 503.0±50.0 °C(Predicted)
• PKA: 4.75±0.10(Predicted)
• PSA: 70.06000
• Density: 1.046±0.06 g/cm3(Predicted)
• LogP: 4.39870
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 14
• Exact Mass: 336.23005950
• Heavy Atom Count: 24
• Complexity: 425

Purity/Quality:

98%Min ^*data from raw suppliers

HepoxilinB ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC1C(O1)C(C=CCC=CCCCC(=O)O)O
• Isomeric SMILES: CCCCCC=CC[C@H]1[C@@H](O1)C(C=CCC=CCCCC(=O)O)O
• Uses: Hepoxilin B is a major eicosanoid produced in the human epidermis and is incorporated onto phospholipids in psoriatic lesions of human epidermis fragments and epidermal cells.

Technology Process of 10-hydroxy-10-[(2S,3S)-3-oct-2-enyloxiran-2-yl]deca-5,8-dienoic acid

There total 67 articles about 10-hydroxy-10-[(2S,3S)-3-oct-2-enyloxiran-2-yl]deca-5,8-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: 91.0%

(5Z,8Z,14Z; 10R,11S,12R)-methyl 10-hydroxy-11,12-epoxyeicosa-5,8,14-trienoate (89461-47-2) → 10(R),11(S),12(S)-hepoxilin B3 (94161-10-1)

Guidance literature:

With lithium hydroxide; In methanol; water; at 23 ℃; for 1.5h;

DOI:10.1016/S0040-4020(01)89921-X

Reference yield: 78.0%

Methyl (10S,11R,12S)-10-hydroxy-11,12,-epoxyeicosa-5(Z),8(Z),14(Z)-trienoate (89408-74-2) → 10(S),11(S),12(S)-hepoxilin B3 (94161-10-1)

Guidance literature:

With lithium hydroxide; In methanol; water; at 23 ℃; for 1.5h;

DOI:10.1016/S0040-4020(01)89921-X

Reference yield:

10(R),11(R),12(R)-hepoxilin B3 methyl ester (160080-80-8) → 10(R),11(R),12(R)-hepoxilin B3 (94161-10-1)

Guidance literature:

With sodium hydroxide; In methanol; at 23 ℃; for 4h;

DOI:10.1016/S0040-4039(00)73491-5

upstream raw materials:

(5Z,8Z,14Z; 10R,11S,12R)-methyl 10-hydroxy-11,12-epoxyeicosa-5,8,14-trienoate

hexylidenetriphenylphosphoran

Methyl (10S,11R,12S)-10-hydroxy-11,12,-epoxyeicosa-5(Z),8(Z),14(Z)-trienoate

(3aR,7S,7aS)-7-Hydroxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

Refernces

• 1、 Nilsson,Ivanov,Oliw. "LC-MS/MS analysis of epoxyalcohols and epoxides of arachidonic acid and their oxygenation by recombinant CYP4F8 and CYP4F22". experimental part. p. 64 - 71. Retrieved 2011/02/21.