14,15-LEUKOTRIENE D4

Base Information

• Chemical Name: 14,15-LEUKOTRIENE D4
• CAS No.: 75290-64-1
• Molecular Formula: C₂₅H₄₀N₂O₆S
• Molecular Weight: 496.668
• Mol file: 75290-64-1.mol

Synonyms:

Chemical Property of 14,15-LEUKOTRIENE D4

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

EoxinD4 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: 14,15-Leukotriene D4 (14,15-LTD4) is a member of an alternate class of LTs synthesized by a pathway involving the dual actions of 15- and 12-lipoxygenases (15- and 12-LOs) on arachidonic acid via 15-HpETE and 14,15-LTA4 intermediates. 14,15-LTD4 is classified as an eoxin (EXD4), because it is formed mostly by eosinophils. However, mast cells and nasal polyps can synthesize 14,15-LTD4 as well. Little is known about the physiological actions of 14,15-LTD4. It has weak contractile activity on both guinea pig ileum and pulmonary parenchyma in contrast to the effects of 5-LO-derived LTs. However, in an in vitro permeability assay, 14,15-LTD4 can increase vascular permeability of human endothelial cell monolayers, with similar potency to that of 5-LO-derived LTs, resulting in plasma leakage, a hallmark of inflammation.
• Uses: Eoxin D4 is synthesized via the 15-lipoxygenase-1 pathway in human eosinophils. Eoxins are proinflammatory arachidonic acid metabolites produced by mast cells.

Technology Process of 14,15-LEUKOTRIENE D4

There total 3 articles about 14,15-LEUKOTRIENE D4 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:

(14S,15S)-leukotriene A4 methyl ester (75290-58-3) + N-(trifluorocysteinyl)glycine methyl ester (80115-80-6) → leukotriene D4 (75290-64-1)

Guidance literature:

With triethylamine; In methanol;

DOI:10.1021/ja00541a060

Reference yield:

methyl 15(S)-hydroperoxy-5(Z),8(Z),11(Z),13(E)-eicosatetraenoate (77026-90-5) → (5Z,8Z,10E,12E)-(14S,15R)-14-[(S)-2-Amino-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-15-hydroxy-icosa-5,8,10,12-tetraenoic acid (75290-64-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 37 percent / PMP, triflic anhydride / CH₂Cl₂ / 2 h / -78 °C

2: 2.) lithium hydroxyde / 2.) 23 deg C, 4 h, 4:1 dimethyoxyethane-water

With lithium hydroxide; trifluoromethylsulfonic anhydride; 2-isovalerylindane-1,3-dione; In dichloromethane;

DOI:10.1016/S0040-4039(00)87339-6

Reference yield:

N-(trifluoroacetyl)-L-cysteinylglycine methyl ester (75290-62-9) + 14,15-EPETE methyl ester (75290-58-3,80629-44-3,136845-36-8) → (5Z,8Z,10E,12E)-(14S,15R)-14-[(S)-2-Amino-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-15-hydroxy-icosa-5,8,10,12-tetraenoic acid (75290-64-1)

Guidance literature:

With lithium hydroxide; Multistep reaction; 2.) 23 deg C, 4 h, 4:1 dimethyoxyethane-water;

DOI:10.1016/S0040-4039(00)87339-6

upstream raw materials:

N-(trifluoroacetyl)-L-cysteinylglycine methyl ester

14,15-EPETE methyl ester

methyl 15(S)-hydroperoxy-5(Z),8(Z),11(Z),13(E)-eicosatetraenoate

(14S,15S)-leukotriene A₄ methyl ester