4-O-Methylhonokiol

4-O-Methylhonokiol

Names
IUPAC name 2-(4-Methoxy-3-prop-2-enylphenyl)-4-prop-2-enylphenol
Other names 3,5′-Diallyl-2′-hydroxy-4-methoxybiphenyl
Identifiers
CAS Number	68592-15-4
ChemSpider	136692
Jmol 3D model	Interactive image
PubChem	155160
InChI InChI=1S/C19H20O2/c1-4-6-14-8-10-18(20)17(12-14)15-9-11-19(21-3)16(13-15)7-5-2/h4-5,8-13,20H,1-2,6-7H2,3H3 Key: OQFHJKZVOALSPV-UHFFFAOYSA-N InChI=1/C19H20O2/c1-4-6-14-8-10-18(20)17(12-14)15-9-11-19(21-3)16(13-15)7-5-2/h4-5,8-13,20H,1-2,6-7H2,3H3 Key: OQFHJKZVOALSPV-UHFFFAOYAP
SMILES COC1=C(C=C(C=C1)C2=C(C=CC(=C2)CC=C)O)CC=C
Properties
Chemical formula	C19H20O2
Molar mass	280.37 g·mol−1
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

4-O-Methylhonokiol is a neolignan, a type of phenolic compounds. It is found in the bark of Magnolia grandiflora and in M. virginiana flowers.

4-O-Methylhonokiol is a potent CB₂ receptor ligand (K_i = 50 nM), showing a unique inverse agonism and partial agonism via different pathways (cAMP and Ca²⁺) and potently inhibits osteoclastogenesis. 4-O-Methylhonokiol further attenuates memory impairment in presenilin 2 mutant mice through reduction of oxidative damage and inactivation of astrocytes and the ERK pathway. The different neuroprotective and anti-Alzheimer Disease effects reported in rodent models may be mediated via CB2 receptors, providing that the compound should be orally bioavailable to the brain. It was shown that 4-O-methylhonokiol activates CB2 receptors and also inhibits the oxygenation of the major endocannabinoid 2-AG via COX-2 in a substrate-selective manner, thus leading to potential synergistic effects at CB receptors. The same study also provided data that this natural product can readily pass the blood–brain barrier, using LC-MS/MS.