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3-[2-(3-Hydroxy-5-methoxyphenyl)ethyl]-6-methoxy-2-(3-methyl-2-butenyl)phenol

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3-[2-(3-Hydroxy-5-methoxyphenyl)ethyl]-6-methoxy-2-(3-methyl-2-butenyl)phenol Basic information

Product Name:
3-[2-(3-Hydroxy-5-methoxyphenyl)ethyl]-6-methoxy-2-(3-methyl-2-butenyl)phenol
Synonyms:
  • 3-[2-(3-Hydroxy-5-methoxyphenyl)ethyl]-6-methoxy-2-(3-methyl-2-butenyl)phenol
  • Canniprene
  • Phenol, 3-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-6-methoxy-2-(3-methyl-2-buten-1-yl)-
CAS:
70677-47-3
MF:
C21H26O4
MW:
342.43
Mol File:
70677-47-3.mol
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3-[2-(3-Hydroxy-5-methoxyphenyl)ethyl]-6-methoxy-2-(3-methyl-2-butenyl)phenol Chemical Properties

Boiling point:
500.3±45.0 °C(Predicted)
Density 
1.128±0.06 g/cm3(Predicted)
pka
9.63±0.10(Predicted)
form 
Solid
color 
White to off-white
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3-[2-(3-Hydroxy-5-methoxyphenyl)ethyl]-6-methoxy-2-(3-methyl-2-butenyl)phenol Usage And Synthesis

Uses

Canniprene, an isoprenylated bibenzyl unique to Cannabis sativa, is a potent inhibitor of 5-lipoxygenase (5-LO) activity (IC50=0.4 μM) and cyclooxygenase/microsomal prostaglandin E2 synthase (PGE2; IC50=10 μM). Canniprene inhibits the production of inflammatory eicosanoids and affects the generation of prostaglandins[1].

IC 50

5-LO: 0.4 μM (IC50); PGE2: 10 μM (IC50)

References

[1] Allegrone G, et al. The Bibenzyl Canniprene Inhibits the Production of Pro-Inflammatory Eicosanoids and Selectively Accumulates in Some Cannabis sativa Strains. J Nat Prod. 2017 Mar 24;80(3):731-734. DOI:10.1021/acs.jnatprod.6b01126

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