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Kavain (+/-) - 10mM in DMSO, high purity , CAS No.500-64-1
a biologically active component of kava that blocks various cationic voltage-gated channels
Basic Description
Synonyms
Kawain | kavain | (+)-Kavain | 500-64-1 | Gonosan | L-KAWAIN | Kavain, dl- | Kawaih | D-Kawain | DTXSID5033595 | W1ES06373M | NSC 112162 | NSC-112162 | (+)-KAWAIN | (R)-(+)-Kavain | CHEBI:6117 | 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-styryl-, (+)- | DTXCID3013595 | (R)-5,6-Dihydro-4-methox
Specifications & Purity
10mM in DMSO
Storage Temp
Store at -80°C
Shipped In
Ice chest + Ice pads
This product requires cold chain shipping. Ground and other economy services are not available.
Product Description
Kavain (+/-), a lipophilic kavapyrone, has been originally extracted from|Piper methysticum|. This compound has been shown to significantly antagonize dopamine depletion in murine striatal neurons. Additional studies report that Kavain (+/-) impairs vascular smooth muscle contraction via inhibition of Ca|+|channels, causing relaxation in precontracted murine ileum, airways, and aortic rings. Furthermore, at high concentrations, this agent has been noted to display neurotoxic characteristics.
Taxonomic Classification
Kingdom
Organic compounds
Superclass
Phenylpropanoids and polyketides
Class
Kavalactones
Subclass
Not available
Intermediate Tree Nodes
Not available
Direct Parent
Kavalactones
Alternative Parents
Styrenes Dihydropyranones Vinylogous esters Enoate esters Lactones Oxacyclic compounds Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
Molecular Framework
Aromatic heteromonocyclic compounds
Substituents
Kavalactone - Styrene - Dihydropyranone - Monocyclic benzene moiety - Pyran - Benzenoid - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Vinylogous ester - Lactone - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organoheterocyclic compound - Oxacycle - Carbonyl group - Hydrocarbon derivative - Organooxygen compound - Organic oxide - Organic oxygen compound - Aromatic heteromonocyclic compound
Description
This compound belongs to the class of organic compounds known as kavalactones. These are lactones, which is structurally characterized by a benzene ring and a pyranone moiety, linked to each other to form a 4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one skeleton.
External Descriptors
Polyketides - alpha-Pyrones
Data sources
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Associated Targets(Human)
Associated Targets(non-human)
Mechanisms of Action
Mechanism of Action
Action Type
target ID
Target Name
Target Type
Target Organism
Binding Site Name
References
Names and Identifiers
IUPAC Name
(2R)-4-methoxy-2-[(E)-2-phenylethenyl]-2,3-dihydropyran-6-one
INCHI
InChI=1S/C14H14O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-8,10,12H,9H2,1H3/b8-7+/t12-/m0/s1
InChIKey
XEAQIWGXBXCYFX-GUOLPTJISA-N
Smiles
COC1=CC(=O)OC(C1)C=CC2=CC=CC=C2
Isomeric SMILES
COC1=CC(=O)O[C@H](C1)/C=C/C2=CC=CC=C2
WGK Germany
3
RTECS
UQ0518000
Molecular Weight
230.3
Beilstein
177877
Reaxy-Rn
84886
Reaxys-RN_link_address
https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=84886&ln=
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
Chemical and Physical Properties
Refractive Index
n20D1.57
Boil Point(°C)
432.64° C at 760 mmHg (Predicted)
Melt Point(°C)
105.5° C
Molecular Weight
230.260 g/mol
XLogP3
2.500
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
3
Exact Mass
230.094 Da
Monoisotopic Mass
230.094 Da
Topological Polar Surface Area
35.500 Ų
Heavy Atom Count
17
Formal Charge
0
Complexity
324.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
1
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
1
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
1
Covalently-Bonded Unit Count
1
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