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Elemicin

$52

  • Brand : BIOFRON

  • Catalogue Number : BD-D1245

  • Specification : 95%(HPLC)

  • CAS number : 487-11-6

  • Formula : C12H16O3

  • Molecular Weight : 208.3

  • Volume : 0.2ML

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Catalogue Number

BD-D1245

Analysis Method

HPLC,NMR,MS

Specification

95%(HPLC)

Storage

-20℃

Molecular Weight

208.3

Appearance

Powder

Botanical Source

Structure Type

Simple Phenylpropanoids

Category

SMILES

COC1=CC(=CC(=C1OC)OC)CC=C

Synonyms

IUPAC Name

Applications

Density

1.011 g/cm3

Solubility

DMSO : ≥ 250 mg/mL (1200.48 mM)
*"≥" means soluble, but saturation unknown.

Flash Point

92.6ºC

Boiling Point

279.8ºC at 760 mmHg

Melting Point

InChl

InChI=1S/C12H16O3/c1-5-6-9-7-10(13-2)12(15-4)11(8-9)14-3/h5,7-8H,1,6H2,2-4H3

InChl Key

BPLQKQKXWHCZSS-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2909300000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:487-11-6) 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

31504590

Abstract

High doses of nutmeg (seeds from Myristica fragrans Houtt.) can be abused as a psychoactive drug due to phenylpropene ingredients. During controlled abstinence, e.g., in forensic psychiatric clinics, nutmeg abuse has to be distinguished from an ingestion of other spices having phenylpropene ingredients (e.g., black pepper or garden lovage) or unintentional low-dose nutmeg intake. The aim of this study was to develop an evaluation model for the estimation of time point and amount of nutmeg abuse and differentiation from ingestion of other spices or low doses of nutmeg based on the gas chromatographic-mass spectrometric (GC-MS) analysis of urine samples. A total of 3 volunteers ingested 1.5 g of freshly ground nutmeg. No symptoms were reported. Urine samples were collected for up to 3 days. In addition, 18 blank samples from volunteers with regular diet and 2 authentic samples from forensic psychiatry patients with supposed nutmeg abuse were analyzed. All samples were analyzed by GC-MS in full scan mode. Metabolites of the nutmeg ingredients safrole, myristicin and elemicin were identified via a library search. For semi-quantitative estimations, the area ratios of the analytes to the internal standard (MDMA-d5) were normalized to the creatinine concentration. Up to 8 different metabolites were detected for at least 18 hours after intake of 1.5 g of nutmeg. In the two authentic samples, the normalized area ratios of those metabolites were 0.5-14 times the maximum reached in the intake study. Two additional metabolites could be detected in authentic samples. Probably due to ingestion of other spices, 5 of the 8 metabolites after intake of 1.5 g of nutmeg were detected in blank urine samples as well. The intake of high doses of nutmeg can be differentiated from the ingestion of other spices or low doses of nutmeg via standard GC-MS analysis of urine and application of the proposed evaluation model.

Title

Detection of Nutmeg Abuse by Gas Chromatography-Mass Spectrometric Screening of Urine

Author

Merja A Neukamm 1 2, Hannes M Schwelm 1 2, Simon Vieser 1 2, Nadine Schiesel 1 2, Volker Auwarter 1 2

Publish date

2020 Jan 7

PMID

31271289

Abstract

Elemicin, an alkenylbenzene constituent of natural oils of several plant species, is widely distributed in food, dietary supplements, and medicinal plants. 1′-Hydroxylation is known to cause metabolic activation of alkenylbenzenes leading to their potential toxicity. The aim of this study was to explore the relationship between elemicin metabolism and its toxicity through comparing the metabolic maps between elemicin and 1′-hydroxyelemicin. Elemicin was transformed into a reactive metabolite of 1′-hydroxyelemicin, which was subsequently conjugated with cysteine (Cys) and N-acetylcysteine (NAC). Administration of NAC could significantly ameliorate the elemicin- and 1′-hydroxyelemicin-induced cytotoxicity of HepG2 cells, while depletion of Cys with diethyl maleate (DEM) increased cytotoxicity. Recombinant human CYP screening and CYP inhibition experiments revealed that multiple CYPs, notably CYP1A1, CYP1A2, and CYP3A4, were responsible for the metabolic activation of elemicin. This study revealed that metabolic activation plays a critical role in elemicin cytotoxicity.

KEYWORDS

1′-hydroxyelemicin; cytotoxicity; elemicin; metabolic activation.

Title

Role of Metabolic Activation in Elemicin-Induced Cellular Toxicity

Author

Yi-Kun Wang 1 2, Xiao-Nan Yang 1 3, Xu Zhu 1 2, Xue-Rong Xiao 1, Xiu-Wei Yang 4, Hong-Bo Qin 1, Frank J Gonzalez 5, Fei Li 1

Publish date

2019 Jul 24

PMID

28273402

Abstract

The essential oil from the leaves of Peperomia borbonensis from Reunion Island was obtained by hydrodistillation and characterized using GC-FID, GC/MS and NMR. The main components were myristicin (39.5%) and elemicin (26.6%). The essential oil (EO) of Peperomia borbonensis and its major compounds (myristicin and elemicin), pure or in a mixture, were evaluated for their insecticidal activity against Bactrocera cucurbitae (Diptera: Tephritidae) using a filter paper impregnated bioassay. The concentrations necessary to kill 50% (LC50 ) and 90% (LC90 ) of the flies in three hours were determined. The LC50 value was 0.23 ± 0.009 mg/cm2 and the LC90 value was 0.34 ± 0.015 mg/cm2 for the EO. The median lethal time (LT50 ) was determined to compare the toxicity of EO and the major constituents. The EO was the most potent insecticide (LT50 = 98 ± 2 min), followed by the mixture of myristicin and elemicin (1.4:1) (LT50 = 127 ± 2 min) indicating that the efficiency of the EO is potentiated by minor compounds and emphasizing one of the major assets of EOs against pure molecules.

KEYWORDS

Bactrocera cucurbitae; Peperomia borbonensis; Elemicin; Essential oil; Insecticidal activities; Myristicin.

Title

Insecticidal Activity of the Leaf Essential Oil of Peperomia borbonensis Miq. (Piperaceae) and Its Major Components against the Melon Fly Bactrocera cucurbitae (Diptera: Tephritidae)

Author

Emmanuelle Dorla 1, Anne Gauvin-Bialecki 1, Zoe Deuscher 1, Agathe Allibert 2, Isabelle Grondin 1, Jean-Philippe Deguine 2, Philippe Laurent 1

Publish date

2017 Jun;