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Dihydrokavain

$572

  • Brand : BIOFRON

  • Catalogue Number : BD-P0233

  • Specification : 98.0%(HPLC)

  • CAS number : 587-63-3

  • Formula : C14H16O3

  • Molecular Weight : 232.28

  • PUBCHEM ID : 10220256

  • Volume : 25mg

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Catalogue Number

BD-P0233

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

-20℃

Molecular Weight

232.28

Appearance

White crystalline powder

Botanical Source

PipermethysticumForst/Root of Piper methysticum and Aniba gigantifolia

Structure Type

Other Compounds

Category

Standards;Natural Pytochemical;API

SMILES

COC1=CC(=O)OC(C1)CCC2=CC=CC=C2

Synonyms

2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-(2-phenylethyl)-/4-Methoxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one/Dihydrokavain/dihydrokawain/2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6- (2-phenylethyl)-, (S)-/(6S)-4-Methoxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one/5,6-Dihydro-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one/2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-(2-phenylethyl)-, (6S)-

IUPAC Name

(2S)-4-methoxy-2-(2-phenylethyl)-2,3-dihydropyran-6-one

Applications

Dihydrokavain is one of the six major kavalactones found in the kava plant; appears to contribute significantly to the anxiolytic effects of kava, based on a study in chicks.

Density

1.1±0.1 g/cm3

Solubility

Ethyl Acetate; Chloroform

Flash Point

175.6±23.3 °C

Boiling Point

413.6±45.0 °C at 760 mmHg

Melting Point

56-60ºC

InChl

InChI=1S/C14H16O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-6,10,12H,7-9H2,1H3

InChl Key

VOOYTQRREPYRIW-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:587-63-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

30739078

Abstract

Due to the widespread occurrence and spread of anthelmintic resistance, there is a need to develop new drugs against resistant parasitic nematodes of livestock animals. The Nobel Prize-winning discovery and development of the anti-parasitic drugs avermectin and artemisinin has renewed the interest in exploring natural products as anthelmintics. In the present study, we screened 7500 plant extracts for in vitro-activity against the barber’s pole worm, Haemonchus contortus, a highly significant pathogen of ruminants. The anthelmintic extracts from two plants, Cryptocarya novoguineensis and Piper methysticum, were fractionated by high-performance liquid chromatography (HPLC). Subsequently, compounds were purified from fractions with significant biological activity. Four α-pyrones, namely goniothalamin (GNT), dihydrokavain (DHK), desmethoxyyangonin (DMY) and yangonin (YGN), were purified from fractions from the two plants, GNT from C. novoguineensis, and DHK, DMY and YGN (= kavalactones) from P. methysticum. The three kavalactones induced a lethal, eviscerated (Evi) phenotype in treated exsheathed third-stage larvae (xL3s), and DMY and YGN had moderate potencies (IC50 values of 31.7 ± 0.23 μM and 23.7 ± 2.05 μM, respectively) at inhibiting the development of xL3s to fourth-stage larvae (L4s). Although GNT had limited potency (IC50 of 200-300 μM) at inhibiting L4 development, it was the only compound that reduced L4 motility (IC50 of 6.25-12.50 μM). The compounds purified from each plant affected H. contortus in an irreversible manner. These findings suggest that structure-activity relationship studies of α-pyrones should be pursued to assess their potential as anthelmintics.

Copyright © 2019 The Authors. Published by Elsevier Ltd.. All rights reserved.

KEYWORDS

Anthelmintic; Cryptocarya novoguineensis; Haemonchus contortus; Natural products; Piper methysticum; α-pyrones

Title

Selected α-pyrones from the plants Cryptocarya novoguineensis (Lauraceae) and Piper methysticum (Piperaceae) with activity against Haemonchus contortus in vitro.

Author

Herath HMPD1, Preston S2, Jabbar A1, Garcia-Bustos J1, Addison RS3, Hayes S3, Rali T4, Wang T1, Koehler AV1, Chang BCH1, Hofmann A5, Davis RA6, Gasser RB7.

Publish date

2019 Apr

PMID

29940660

Abstract

Piper methysticum (Kava) is a plant whose roots are used in the preparation of traditional beverages with spiritual, medicinal, and social importance for the Pacific Islanders. Kava is also sold as a herbal supplement or recreational beverage consumed for its mild inebriating effect in Europe and North America. With an ongoing interest in the safety and quality of kava products, it is necessary to develop a validated method for determination of kava chemical composition to ensure confidence in quality assessment. Thus, an high-performance liquid chromatography with ultraviolet detection (HPLC-UV) method was developed, optimized, and validated for determining six major kavalactones and three flavokavains in kava raw materials and finished products based on AOAC single-laboratory validation guidelines. This is the first fully validated analytical method for measuring kavalactones and flavokavains in a single run. The separation of the analytes was achieved in 10 min with an Agilent Poroshell C18 column using gradient separation. The sample was extracted with methanol first and then acetone. The signals were detected at 240 nm and 355 nm. The limit of quantification was under 1.2 µg/mL (0.3 mg/g) for kavalactones and under 0.35 µg/mL (0.01 mg/g) for flavokavains. The Horwitz ratio values described ranged from 0.3 to 1.82. The spike recovery experiments showed an accuracy between 92 and 105% for all analytes. The results of the study demonstrate that the method is fit for the purpose of determining methysticin, dihydromethysticin, kavain, dihydrokavain, yangonin, desmethoxyyangonin, flavokavain A, flavokavain B, and flavokavain C in kava raw material and finished products (dry-filled capsule, liquid phytocaps, and tincture).

Georg Thieme Verlag KG Stuttgart · New York.

Title

Single-Lab Validation for Determination of Kavalactones and Flavokavains in Piper methysticum (Kava).

Author

Liu Y1, Lund JA2, Murch SJ2, Brown PN1.

Publish date

2018 Nov

PMID

29795658

Abstract

Kava is regaining its popularity with detailed characterizations warranted. We developed an ultraperformance liquid chromatography high-resolution tandem mass spectrometry (UPLC-MS/MS) method for major kavalactones (kavain, dihydrokavain, methysticin, dihydromethysticin and desmethoxyyangonin) with excellent selectivity and specificity. The method has been validated for different matrices following the Food and Drug Administration guidance of analytical procedures and methods validation. The scope of this method has been demonstrated by quantifying these kavalactones in two kava products, characterizing their tissue distribution and pharmacokinetics in mice, and detecting their presence in human urines and plasmas upon kava intake. As expected, the abundances of these kavalactones differed significantly in kava products. All of them exhibited a large volume of distribution with extensive tissue affinity and adequate mean residence time (MRT) in mice. This method also successfully quantified these kavalactones in human body fluids upon kava consumption at the recommended human dose. This UPLC-MS/MS method therefore can be used to characterize kava products and its pharmacokinetics in animals and in humans.

Title

A stable isotope dilution tandem mass spectrometry method of major kavalactones and its applications.

Author

Wang Y1, Eans SO2, Stacy HM2, Narayanapillai SC1,3, Sharma A4, Fujioka N5, Haddad L6, McLaughlin J2, Avery BA4, Xing C1,3.

Publish date

2018 May 24