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Kakuol

$300

  • Brand : BIOFRON

  • Catalogue Number : BF-K4003

  • Specification : 98%(HPLC)

  • CAS number : 18607-90-4

  • Formula : C10H10O4

  • Molecular Weight : 194.184

  • PUBCHEM ID : 596894

  • Volume : 25mg

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Catalogue Number

BF-K4003

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

194.184

Appearance

Off-white powder

Botanical Source

Asarum heterotropoides

Structure Type

Phenolics

Category

Standards;Natural Pytochemical;API

SMILES

CCC(=O)C1=CC2=C(C=C1O)OCO2

Synonyms

1-Propanone,1-(6-hydroxy-1,3-benzodioxol-5-yl)/1-(6-hydroxy-1,3-benzodioxol-5-yl)propan-1-one/2-hydroxy-4,5-(methylenedioxy)propiophenone/kakuol/1-(6-Hydroxy-1,3-benzodioxol-5-yl)-1-propanone/1-(6-hydroxy-benzo[1,3]dioxol-5-yl)-propan-1-one/Kakoul/1-Propanone, 1-(6-hydroxy-1,3-benzodioxol-5-yl)-/1-[2-hydroxy-4,5-(methylenedioxy)phenyl]propan-1-one/2-Hydroxy-4,5-methylenedioxypropiophenone

IUPAC Name

1-(6-hydroxy-1,3-benzodioxol-5-yl)propan-1-one

Density

1.3±0.1 g/cm3

Solubility

Ethyl Acetate

Flash Point

143.3±21.4 °C

Boiling Point

352.3±42.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C10H10O4/c1-2-7(11)6-3-9-10(4-8(6)12)14-5-13-9/h3-4,12H,2,5H2,1H3

InChl Key

SLLMHZXMVHNZOR-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#:18607-90-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

23262316

Abstract

Topoisomerases IB are anticancer and antimicrobial targets whose inhibition by several natural and synthetic compounds has been documented over the last three decades. Here we show that kakuol, a natural compound isolated from the rhizomes of Asarum sieboldii, and a derivative analogue are able to inhibit the DNA relaxation mediated by the human enzyme. The analogue is the most efficient one and the inhibitory effect is enhanced upon pre-incubation with the enzyme. Analysis of the different steps of the catalytic cycle indicates that the inhibition occurs at the cleavage level and does not prevent DNA binding. Molecular docking shows that the compound preferentially binds near the active site at the bottom of the catalytic residue Tyr723, providing an atomistic explanation for its inhibitory activity.

Title

A Derivative of the Natural Compound Kakuol Affects DNA Relaxation of Topoisomerase IB Inhibiting the Cleavage Reaction

Author

Silvia Castelli 1 , Sara Vieira, Ilda D'Annessa, Prafulla Katkar, Loana Musso, Sabrina Dallavalle, Alessandro Desideri

Publish date

2013 Feb 1

PMID

31685339

Abstract

In continuation of our program to discover new potential antifungal agents, a series of amide and imine derivatives containing a kakuol moiety were synthesized and characterized by the spectroscopic analysis. By using the mycelium growth rate method, the target compounds were evaluated systematically for antifungal activities in vitro against four plant pathogenic fungi, and structure-activity relationships (SAR) were derived. Compounds 7d, 7e, 7h, 7i and 7r showed obvious inhibitory activity against the corresponding tested fungi at 50 μg/mL. Especially, compounds 7e and 7r displayed more potent antifungal activity against B. cinerea than that of thiabendazole (a positive control). Moreover, compound 7e also exhibited good activity against A. alternata with EC50 values of 11.0 µg/mL, and the value was slightly superior to that of thiabendazole (EC50 = 14.9 µg/mL). SAR analysis showed that the ether group was a highly sensitive structural moiety to the activity and the type as well as position of substituents on benzene ring could make some effects on the activity.

Title

Design, Synthesis and Antifungal Activity of Amide and Imine Derivatives Containing a Kakuol Moiety

Author

Guoqing Sui 1 , Dan Xu 2 , Tianlong Luo 1 , Huihui Guo 1 , Gang Sheng 1 , Dongrui Yin 1 , Li Ren 1 , Hongdong Hao 3 , Wenming Zhou 4

Publish date

2020 Jan 1

PMID

15846774

Abstract

An antifungal substance active against Colletotrichum orbiculare (Berk & Mont) Arx was isolated from the methanol extracts of Asarum sieboldii (Miq) Maek rhizomes. High-resolution MS, NMR and UV spectral data confirmed that the antifungal substance is kakuol, 2-hydroxy-4,5-methylenedioxypropiophenone. Colletotrichum orbiculare was most sensitive to kakuol, with MIC of 10 microg ml(-1). Kakuol also completely inhibited the mycelial growth of Botrytis cinerea Pers ex Fr and Cladosporium cucumerinum Ellis & Arthur at 50 microg ml(-1) and 30 microg ml(-1), respectively. However, no antimicrobial activity was found against yeast and bacteria even at 100 microg ml(-1). Kakuol exhibited a protective activity against the development of anthracnose disease on cucumber plants. The control efficacy of kakuol against the anthracnose disease was in general somewhat less than that of the commercial fungicide chlorothalonil. This is the first report to demonstrate in vitro and in vivo antifungal activity of kakuol against C. orbiculare infection.
2005 Society of Chemical Industry

Title

Isolation and Antifungal Activity of Kakuol, a Propiophenone Derivative From Asarum Sieboldii Rhizome

Author

Jung Yeop Lee 1 , Surk Sik Moon, Byung Kook Hwang

Publish date

2005 Aug


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