2-Arachidonyl glyceryl ether

2-Arachidonyl glyceryl ether
Names
IUPAC name
2-O-[(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetrae-1-yl]glycerol
Systematic IUPAC name
2-{[(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraen-1-yl]oxy}propane-1,3-diol
Other names
2-AGE, 2-arachidonylglyceryl ether, Noladin ether, Noladin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C23H40O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26-23(21-24)22-25/h6-7,9-10,12-13,15-16,23-25H,2-5,8,11,14,17-22H2,1H3/b7-6-,10-9-,13-12-,16-15- checkY
    Key: CUJUUWXZAQHCNC-DOFZRALJSA-N checkY
  • InChI=1/C23H40O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26-23(21-24)22-25/h6-7,9-10,12-13,15-16,23-25H,2-5,8,11,14,17-22H2,1H3/b7-6-,10-9-,13-12-,16-15-
    Key: CUJUUWXZAQHCNC-DOFZRALJBH
  • OCC(OCCCC\C=C/C/C=C\C\C=C/C\C=C/CCCCC)CO
Properties
C23H40O3
Molar mass 364.56 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Arachidonyl glyceryl ether (2-AGE, Noladin ether) is a putative endocannabinoid discovered by Lumír Hanuš and colleagues at the Hebrew University of Jerusalem, Israel. It is an ether formed from the alcohol analog of arachidonic acid and glycerol. Its isolation from porcine brain and its structural elucidation and synthesis were described in 2001.[1]

  1. ^ Hanus, L.; Abu-Lafi, S.; Fride, E.; Breuer, A.; Vogel, Z.; Shalev, D.; Kustanovich, I.; Mechoulam, R. (2001). "2-Arachidonyl glyceryl ether, an endogenous agonist of the cannabinoid CB1 receptor". Proceedings of the National Academy of Sciences. 98 (7): 3662–3665. Bibcode:2001PNAS...98.3662H. doi:10.1073/pnas.061029898. PMC 31108. PMID 11259648.