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DIHYDROMETHYSTICIN

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DIHYDROMETHYSTICIN Basic information

Product Name:
DIHYDROMETHYSTICIN
Synonyms:
  • 6-(2-(1,3-benzodioxol-5-yl)ethyl)-5,6-dihydro-4-methoxy-2h-pyran-2-on(s)
  • 6-dihydro-4-methoxy-6-(3,4-(methylenedioxy)phenethyl)-(s)-2h-pyran-2-on
  • 7,8-dihydromethysticin
  • dhm
  • DIHYDROMETHYLSTICIN
  • 7,8-DIHYDROMETHYLSTICIN
  • 5,6-Dihydro-4-methoxy-6-[2-(1,3-benzodioxol-5-yl)ethyl]-2H-pyran-2-one
  • 6-[2-(1,3-Benzodioxol-5-yl)ethyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one
CAS:
19902-91-1
MF:
C15H16O5
MW:
276.28
Product Categories:
  • Coumarins
Mol File:
19902-91-1.mol
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DIHYDROMETHYSTICIN Chemical Properties

storage temp. 
2-8°C
solubility 
Chloroform (Slightly), Methanol (Slightly), Pyridine (Slightly)
Boiling point:
476.1±45.0 °C(Predicted)
Density 
1.28±0.1 g/cm3(Predicted)
Melting point:
117-118 °C
form 
Solid
color 
White to Off-White
BRN 
91699
Stability:
Hygroscopic
InChIKey
RSIWXFIBHXYNFM-NSHDSACASA-N
LogP
1.810 (est)
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Safety Information

WGK Germany 
3
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DIHYDROMETHYSTICIN Usage And Synthesis

Description

Dihydromethysticin is a kavalactone originally isolated from P. methysticum (kava-kava) that has diverse biological activities, including efflux transporter inhibitory, antinociceptive, and neuroprotective properties. Dihydromethysticin is a P-glycoprotein (P-gp) inhibitor that increases uptake of the P-gp substrate calcein AM by 50% in P388 mouse leukemia cancer cells overexpressing P-gp when used at a concentration of 54.6 μM. Dihydromethysticin (275 mg/kg) has analgesic activity, increasing the latency to tail withdrawal in the tail-flick assay in mice. It also decreases the infarct size in a mouse model of ischemia induced by microbipolar coagulation of the left middle cerebral artery (MCA) when administered at a dose of 10 mg/kg.

Uses

(6S)-6-[2-(1,3-Benzodioxol-5-yl)ethyl]-5,6-dihydro-4-methoxy-2H-pyran-2-one, is used in toxicity studies through in vitro analysis. This complex is found in the roots of kava plant.

Definition

ChEBI: Dihydromethysticin is a member of 2-pyranones and an aromatic ether.

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