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Dehydrodiisoeugenol

$143

  • Brand : BIOFRON

  • Catalogue Number : BF-D2031

  • Specification : 98%

  • CAS number : 2680-81-1

  • Formula : C20H22O4

  • Molecular Weight : 326.39

  • PUBCHEM ID : 5379033

  • Volume : 20mg

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Catalogue Number

BF-D2031

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

326.39

Appearance

White flake crystal

Botanical Source

Myristica fragrans,Schisandra chinensis,Litsea lancifolia,Kadsura coccinea

Structure Type

Lignanoids

Category

Standards;Natural Pytochemical;API

SMILES

CC=CC1=CC2=C(C(=C1)OC)OC(C2C)C3=CC(=C(C=C3)O)OC

Synonyms

Isoeugenol,dehydrodi/DEHRODIISOEUGENOL/Phenol, 4-[2,3-dihydro-7-methoxy-3-methyl-5-[(1E)-1-propen-1-yl]-2-benzofuranyl]-2-methoxy-/Diisoeugenol,dehydro/dehydrodiisoeugenol/2-Methoxy-4-{7-methoxy-3-methyl-5-[(1E)-1-propen-1-yl]-2,3-dihydro-1-benzofuran-2-yl}phenol

IUPAC Name

2-methoxy-4-[7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydro-1-benzofuran-2-yl]phenol

Density

1.2±0.1 g/cm3

Solubility

Methanol; Acetontrile; DMSO

Flash Point

227.2±28.7 °C

Boiling Point

452.0±45.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C20H22O4/c1-5-6-13-9-15-12(2)19(24-20(15)18(10-13)23-4)14-7-8-16(21)17(11-14)22-3/h5-12,19,21H,1-4H3/b6-5-

InChl Key

ITDOFWOJEDZPCF-WAYWQWQTSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:2680-81-1) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

925912

Abstract

The ethanol-water extract of Aristolochia taliscana Hook and Arn (Aristolochiaceae) yielded a compound which was identified as dehydrodiisoeugenol by means of elemental analysis, IR, UV, NMR, and mass spectra, and direct comparison with a synthetic sample.

Title

Dehydrodiisoeugenol: A Naturally Occurring Lignan From Aristolochia Taliscana (Aristolochiaceae)

Author

F Ionescu, S D Jolad, J R Cole

Publish date

1977

PMID

15639233

Abstract

o-Methoxyphenols such as eugenol and isoeugenol exhibit anti-oxidant and anti-inflammatory activities, but at higher concentrations act as oxidants and potent allergens. We recently demonstrated the eugenol dimer bis-eugenol to be an efficient inhibitor of lipopolysaccharide (LPS)-induced inflammatory cytokine expression in macrophages without cytotoxicity. This result suggested that dimer compound of o-methoxyphenols may possess anti-inflammatory activity. Thus, we further synthesized dehydrodiisoeugenol and alpha-diisoeugenol from isoeugenols, and investigated whether these dimers could inhibit LPS-stimulated nuclear factor kappa B (NF-kappaB) activation and cyclooxygenase (COX)-2 gene expression, both of which are closely involved in inflammation and mutagenesis. The expression of the COX-2 gene was strongly inhibited by dehydrodiisoeugenol in RAW264.7 murine macrophages stimulated with LPS. In contrast, isoeugenol and alpha-diisoeugenol did not inhibit it. Dehydrodiisoeugenol also significantly inhibited LPS-stimulated phosphorylation-dependent proteolysis of inhibitor kappaB-alpha and transcriptional activity of NF-kappaB in the cells. These findings suggest that dehydrodiisoeugenol acts as a potent anti-inflammatory agent.

Title

Dehydrodiisoeugenol, an Isoeugenol Dimer, Inhibits Lipopolysaccharide-Stimulated Nuclear Factor Kappa B Activation and cyclooxygenase-2 Expression in Macrophages

Author

Yukio Murakami 1 , Masao Shoji, Atsushi Hirata, Shoji Tanaka, Ichiro Yokoe, Seiichiro Fujisawa

Publish date

2005 Feb 15

PMID

28806569

Abstract

Dehydrodiisoeugenol (DDIE), a representative and major benzofuran-type neolignan in Myristica fragrans Houtt., shows anti-inflammatory and anti-bacterial actions. In order to better understand its pharmacological properties, xenobiotic metabolomics was used to determine the metabolic map of DDIE and its influence on endogenous metabolites. Total thirteen metabolites of DDIE were identified through in vivo and in vitro metabolism, and seven of them were reported for the first time in the present study. The identity of DDIE metabolites was achieved by comparison of the MS/MS fragmentation pattern with DDIE using ultra-performance chromatography electrospray ionization quadrupole time-of-flight mass spectrometry (UPLC-ESI- QTOFMS). Demethylation and ring-opening reaction were the major metabolic pathways for in vivo metabolism of DDIE. Recombinant cytochrome P450s (CYPs) screening revealed that CYP1A1 is a primary enzyme contributing to the formation of metabolites D1-D4. More importantly, the levels of two endogenous metabolites 2,8-dihydroxyquinoline and its glucuronide were significantly elevated in mouse urine after DDIE exposure, which explains in part its modulatory effects on gut microbiota. Taken together, these data contribute to the understanding of the disposition and pharmacological activities of DDIE in vivo.

KEYWORDS

Dehydrodiisoeugenol; Metabolic profiling; UPLC-ESI-QTOFMS; Xenobiotic metabolomics.

Title

Metabolic Profiling of Dehydrodiisoeugenol Using Xenobiotic Metabolomics

Author

Qian-Qian Lv 1 , Xiao-Nan Yang 2 , Dong-Mei Yan 3 , Wei-Qing Liang 4 , Hong-Ning Liu 5 , Xiu-Wei Yang 6 , Fei Li 7

Publish date

2017 Oct 25


Description :

Dehydrodiisoeugenol is isolated from Myristica fragrans Houtt, shows anti-inflammatory and anti-bacterial actions[1]. Dehydrodiisoeugenol inhibits LPS- stimulated NF-κB activation and cyclooxygenase (COX)-2 gene expression in murine macrophages[2].