| Identification | Back Directory | [Name]
DIHYDROMETHYSTICIN | [CAS]
19902-91-1 | [Synonyms]
dhm
Nsc112159
PseudoMethysticin
DIHYDROMETHYSTICIN
DIHYDROMETHYLSTICIN
7,8-dihydromethysticin
7,8-DIHYDROMETHYLSTICIN
Methysticin, 7,8-dihydro-
Dihydromethysticin ((+)-Dihydromethysticin)
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
6-dihydro-4-methoxy-6-(3,4-(methylenedioxy)phenethyl)-(s)-2h-pyran-2-on
6-(2-(1,3-benzodioxol-5-yl)ethyl)-5,6-dihydro-4-methoxy-2h-pyran-2-on(s)
(6S)-6-[2-(1,3-Benzodioxol-5-yl)ethyl]-5,6-dihydro-4-Methoxy-2H-pyran-2-one
2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-[3,4-(methylenedioxy)phenethyl]-, (S)-
2H-Pyran-2-one, 6-[2-(1,3-benzodioxol-5-yl)ethyl]-5,6-dihydro-4-methoxy-, (S)-
2H-Pyran-2-one, 6-[2-(1,3-benzodioxol-5-yl)ethyl]-5,6-dihydro-4-methoxy-, (6S)- | [Molecular Formula]
C15H16O5 | [MDL Number]
MFCD00221731 | [MOL File]
19902-91-1.mol | [Molecular Weight]
276.28 |
| Chemical Properties | Back Directory | [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) | [form ]
neat | [Melting point ]
117-118 °C | [color ]
White to Off-White | [BRN ]
91699 | [Stability:]
Hygroscopic | [Major Application]
food and beverages | [InChI]
InChI=1S/C15H16O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h3,5-6,8,11H,2,4,7,9H2,1H3/t11-/m0/s1 | [InChIKey]
RSIWXFIBHXYNFM-NSHDSACASA-N | [SMILES]
C1(=O)O[C@@H](CCC2=CC=C3OCOC3=C2)CC(OC)=C1 | [LogP]
1.810 (est) |
| Hazard Information | Back Directory | [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. | [Chemical Properties]
White crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from the rhizome of Pipermethysticum Forst. | [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. | [IC 50]
CYP3 | [storage]
4°C, protect from light | [References]
[1] D. D. JAMIESON P. H D. THE ANTINOCICEPTIVE ACTIONS OF KAVA COMPONENTS IN MICE[J]. Clinical and Experimental Pharmacology and Physiology, 1990, 17 7: 495-507. DOI: 10.1111/j.1440-1681.1990.tb01349.x
[2] CORD BACKHAUΒ Josef K. Extract of kava (Piper methysticum) and its methysticin constituents protect brain tissue against ischemic damage in rodents[J]. European journal of pharmacology, 1992, 215 2: Pages 265-269. DOI: 10.1016/0014-2999(92)90037-5
[3] JOHANNA WEISS. Extracts and kavalactones of Piper methysticum G. Forst (kava-kava) inhibit P-glycoprotein in vitro.[J]. Drug Metabolism and Disposition, 2005, 33 11: 1580-1583. DOI: 10.1124/dmd.105.005892 |
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