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Eugenol acetate

$52

  • Brand : BIOFRON

  • Catalogue Number : BD-D1251

  • Specification : 97%(HPLC)

  • CAS number : 93-28-7

  • Formula : C12H14O3

  • Molecular Weight : 206.24

  • Volume : 0.1ML

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Catalogue Number

BD-D1251

Analysis Method

HPLC,NMR,MS

Specification

97%(HPLC)

Storage

2-8°C

Molecular Weight

206.24

Appearance

liquid

Botanical Source

Structure Type

Simple Phenylpropanoids

Category

SMILES

Synonyms

IUPAC Name

Applications

Density

1.1±0.1 g/cm3

Solubility

Flash Point

106.8±18.6 °C

Boiling Point

268.0±28.0 °C at 760 mmHg

Melting Point

26°C

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2915390000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:93-28-7) 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

29026308

Abstract

Metastatic melanoma is an aggressive cancer with increasing incidence and limited therapies in advanced stages. Systemic neutrophilia or abundant neutrophils in the tumor contribute toward its worst prognosis, and the interplay of cancer and the immune system has been shown in tumor development and metastasis. We recently showed the in vivo efficacy of poly(ε-caprolactone) lipid-core nanocapsule (LNC) or LNC loaded with acetyleugenol (AcE-LNC) to treat B16F10-induced melanoma in mice. In this study, we investigated whether LNC or AcE-LNC toxicity could involve modifications on crosstalk of melanoma cells and neutrophils. Therefore, melanoma cells (B16F10) were pretreated with vehicle, LNC, AcE or AcE-LNC for 24 h, washed and, further, cocultured for 18 h with peritoneal neutrophils obtained from C57Bl/6 mice. Melanoma cells were able to internalize the LNC or AcE-LNC after 2 h of incubation. LNC or AcE-LNC pretreatments did not cause melanoma cells death, but led melanoma cells to be more susceptible to death in serum deprivation or hypoxia or in the presence of neutrophils. Interestingly, the production of reactive oxygen species (ROS), which causes cell death, was increased by neutrophils in the presence of LNC- and AcE-LNC-pretreated melanoma cells. LNC or AcE-LNC treatments reduced the concentration of transforming growth factor-β (TGF-β) in the supernatant of melanoma cells, a known factor secreted by cancer cells to induce pro-tumoral actions of neutrophils in the tumor microenvironment. In addition, we found reduced levels of pro-tumoral chemical mediators VEGF, arginase-1, interleukin-10 (IL-10) and matrix metalloproteinase-9 (MMP-9) in the supernatant of LNC or AcE-LNC-pretreated melanoma cells and cocultured with neutrophils. Overall, our data show that the uptake of LNC or AcE-LNC by melanoma cells affects intracellular mechanisms leading to more susceptibility to death and also signals higher neutrophil antitumoral activity.

KEYWORDS

LNC; acetyleugenol; apoptosis; coculture; hypoxia; intravital microscopy; serum deprivation; tumor microenvironment.

Title

Role of poly(ε-caprolactone) lipid-core nanocapsules on melanoma-neutrophil crosstalk

Author

Carine C Drewes 1, Aline de Cs Alves 2 3, Cristina B Hebeda 1, Isabela Copetti 2 3, Silvana Sandri 1, Mayara K Uchiyama 4, Koiti Araki 4, Silvia S Guterres 2, Adriana R Pohlmann 2 3, Sandra H Farsky 1

Publish date

2017 Sep 27;

PMID

27452957

Abstract

The study evaluated the efficiency of eugenyl acetate (EA), a phytochemical in clove essential oil, against clinical isolates of Candida albicans, Candida parapsilosis, Candida tropicalis, and Candida glabrata. Minimum inhibitory concentrations (MIC) of EA against Candida isolates were in the range between 0.1% and 0.4% (v/v). Spot assay further confirmed the susceptibility of Candida isolates to the compound upon treatment with respective 1 × MIC. Growth profile measured in time kill study evidence that the compound at 1 × MIC and 1/2 × MIC retarded the growth of Candida cells, divulging the fungicidal activity. Light microscopic observation demonstrated that upon treated with EA, rough cell morphology, cell damage, and fragmented patterns were observed in C. albicans, C. parapsilosis, C. tropicalis, and C. glabrata. Furthermore, unusual morphological changes of the organism were observed in scanning electron microscopic study. Therefore, it is validated that the compound could cause cell damage resulting in the cell death of Candida clinical isolates. Eventually, the compound at sub-MIC (0.0125% v/v) significantly inhibited serum-induced germ tube formation by C. albicans. Eugenyl acetate inhibited biofilm forming ability of the organisms as well as reduced the adherence of Candida cells to HaCaT keratinocytes cells. In addition, upon treatment with EA, the phagocytic activity of macrophages was increased significantly against C. albicans (P < 0.05). The results demonstrated the potential of EA as a valuable phytochemical to fight against emerging Candida infections.

KEYWORDS

Biofilm formation; Candida albicans; Candida glabrata; Candida parapsilosis; Candida tropicalis; Cell damage; Eugenyl acetate; Phagocytic activity; antifungal activity.

Title

Antifungal potential of eugenyl acetate against clinical isolates of Candida species

Author

Khadar Syed Musthafa 1, Jutharat Hmoteh 2, Benjamas Thamjarungwong 3, Supayang Piyawan Voravuthikunchai 4

Publish date

2016 Oct

PMID

27382998

Abstract

The production of compounds via enzymatic esterification has great scientific and technological interest due to the several inconveniences related to acid catalysis, mainly by these systems do not fit to the concept of “green chemistry”. Besides, natural products as clove oil present compounds with excellent biological potential. Bioactives compounds are often toxic at high doses. The evaluation of lethality in a less complex animal organism can be used to a monitoring simple and rapid, helping the identification of compounds with potential insecticide activity against larvae of insect vector of diseases. In this sense, the toxicity against Artemia salina of clove essential oil and its derivative eugenyl acetate obtained by enzymatic esterification using Novozym 435 as biocatalyst was evaluated. The conversion of eugenyl acetate synthesis was 95.6%. The results about the evaluation of toxicity against the microcrustacean Artemia salina demonstrated that both oil (LC50= 0.5993 µg.mL-1) and ester (LC50= 0.1178 µg.mL-1) presented high toxic potential, being the eugenyl acetate almost 5 times more toxic than clove essential oil. The results reported here shows the potential of employing clove oil and eugenyl acetate in insecticide formulations.

Title

Toxicity of clove essential oil and its ester eugenyl acetate against Artemia salina

Author

R L Cansian 1, A B Vanin 1, T Orlando 1, S P Piazza 1, B M S Puton 1, R I Cardoso 1, I L Goncalves 1, T C Honaiser 1, N Paroul 1, D Oliveira 2

Publish date

2017 Mar-Apr