Shipping to United States We Offer Worldwide Shipping
Login Wishlist

Zingerone

$38

  • Brand : BIOFRON

  • Catalogue Number : AV-P12182

  • Specification : 98%

  • CAS number : 122-48-5

  • Formula : C11H14O3

  • Molecular Weight : 194.23

  • PUBCHEM ID : 31211

  • Volume : 25mg

Available on backorder

Quantity
Checkout Bulk Order?

Catalogue Number

AV-P12182

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

194.23

Appearance

Colorless columnar crystal

Botanical Source

Zingiber officinale Rosc.

Structure Type

Simple Phenolic Compounds

Category

Standards;Natural Pytochemical;API

SMILES

CC(=O)CCC1=CC(=C(C=C1)O)OC

Synonyms

Vanillyl acetone/4-(4-Hydroxy-3-methoxyphenyl)-2-butanone/4-(4-hydroxy-3-methoxyphenyl)butan-2-one//Zingiberone/2-Butanone, 4-(4-hydroxy-3-methoxyphenyl)-/Vanillylacetone/3-Methoxy-4-hydroxybenzylacetone/2-Butanone, 4- (4-hydroxy-3-methoxyphenyl)-/Zingberone/zingerone

IUPAC Name

4-(4-hydroxy-3-methoxyphenyl)butan-2-one

Applications

Zingerone (Vanillylacetone) is a nontoxic methoxyphenol isolated from Zingiber officinale, with potent anti-inflammatory, antidiabetic, antilipolytic, antidiarrhoeic, antispasmodic and anti-tumor[3] properties[1]. Zingerone alleviates oxidative stress and inflammation, down-regulates NF-κB mediated signaling pathways[2]. Zingerone acts as an anti-mitotic agent, and inhibits the growth of neuroblastoma cells[3].

Density

1.1±0.1 g/cm3

Solubility

Methanol; DMSO

Flash Point

123.7±17.2 °C

Boiling Point

323.0±27.0 °C at 760 mmHg

Melting Point

40-41 °C(lit.)

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:122-48-5) 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

30235818

Abstract

Cancer cells undergo uncontrolled proliferation resulting from aberrant activity of various cell-cycle proteins. Therefore, despite recent advances in intensive chemotherapy, it is difficult to cure cancer completely. Recently, cell-cycle regulators became attractive targets in cancer therapy. Zingerone, a phenolic compound isolated from ginger, is a nontoxic and inexpensive compound with varied pharmacological activities. In this study, the therapeutic effect of zingerone as an anti-mitotic agent in human neuroblastoma cells was investigated. Following treatment of BE(2)-M17 cells with zingerone, we performed a 3-(4,5-dimethylthiazol-2-yl)-2,5- diphenyltetrazolium bromide (MTT) assay and colony-formation assay to evaluate cellular proliferation, in addition to immunofluorescence cytochemistry and flow cytometry to examine the mitotic cells. The association of gene expression with tumor stage and survival was analyzed. Furthermore, to examine the anti-cancer effect of zingerone, we applied a BALB/c mouse-tumor model using a BALB/c-derived adenocarcinoma cell line. In human neuroblastoma cells, zingerone inhibited cellular viability and survival. Moreover, the number of mitotic cells, particularly those in prometaphase, increased in zingerone-treated neuroblastoma cells. Regarding specific molecular mechanisms, zingerone decreased cyclin D1 expression and induced the cleavage of caspase-3 and poly (ADP-ribose) polymerase 1 (PARP-1). The decrease in cyclin D1 and increase in histone H3 phosphorylated (p)-Ser10 were confirmed by immunohistochemistry in tumor tissues administered with zingerone. These results suggest that zingerone induces mitotic arrest followed by inhibition of growth of neuroblastoma cells. Collectively, zingerone may be a potential therapeutic drug for human cancers, including neuroblastoma.

KEYWORDS

apoptosis; cyclin D1; mitosis arrest; tumor progression; zingerone.

Title

Zingerone Suppresses Tumor Development Through Decreasing Cyclin D1 Expression and Inducing Mitotic Arrest

Author

Jae-Sun Choi 1 2 , Jaewook Ryu 3 , Woom-Yee Bae 4 , Aron Park 5 , Seungyoon Nam 6 7 8 , Ja-Eun Kim 9 10 , Joo-Won Jeong 11 12

Publish date

2018 Sep 19

PMID

29117507

Abstract

The epidermis, the outermost layer of the skin, is a stratified epithelium that protects the body from the external environment. Keratinocyte stem cells (KSCs) are involved in epidermis homeostasis by maintaining epidermal integrity through a process of constant regeneration. Ultraviolet B (UVB) radiation is a major inducer of cellular damage in the epidermis. In this study, we investigated the effects of zingerone (a phenolic compound derived from spices) on UVB-induced cellular damage in KSCs. We found that zingerone significantly inhibited cellular senescence of KSCs in response to UVB irradiation. These effects were confirmed by the senescence-associated β-galactosidase and comet assays. Zingerone decreased the production of proinflammatory cytokines such as tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β), and interleukin-6 (IL-6) in UVB-irradiated KSCs. Moreover, UVB-induced expression of p21, a cell cycle arrest-related gene, was reduced by zingerone treatment, whereas zingerone upregulated the expression of proliferation-related genes such as proliferating cell nuclear antigen (PCNA) and vascular endothelial growth factor (VEGF), in addition to anti-senescence-related genes including telomerase reverse transcriptase (TERT), histone deacetylase 1 (HDAC1), and DNA (cytosine-5)-methyltransferase 1 (DNMT1). The UVB-protective effects of zingerone were mediated by inhibition of p42/44 MAPK and p38 MAPK. Therefore, zingerone could potentially be used to protect the epidermis from UVB-induced damage.

KEYWORDS

AP-1; Cellular damage; Keratinocyte stem cells; Ultraviolet B; Zingerone.

Title

Zingerone Protects Keratinocyte Stem Cells From UVB-induced Damage

Author

Jienny Lee 1 , Sae Woong Oh 2 , Seoung Woo Shin 3 , Kyung-Woo Lee 4 , Jae-Youl Cho 5 , Jongsung Lee 6

Publish date

2018 Jan 5

PMID

29367111

Abstract

Diabetes affects a large proportion of population wide across the world and kidney is a main target organ of diabetic complications. Zingerone is a stable active component derived from dry ginger rhizome. We investigated the effect of zingerone on diabetic nephropathy and explored the possible mechanisms. We showed that zingerone decreased the levels of serum insulin, C-peptide and glycosylated hemoglobin A1c. The levels of blood urea nitrogen (BUN), serum creatinine, urinary albumin content and albumin/creatinine ratio (ACR) were reduced by zingerone. Moreover, zingerone attenuated the pathological injuries of kidneys, reduced the surface area of Bowman’s capsule, Bowman’s space, glomerular tuft, and decreased the expression of collagen IV and fibronectin in kidneys in db/db mice. The high levels of triglyceride and cholesterol, and high expression of TNF? and IL-6 were decreased by zingerone. Furthermore, zingerone decreased the level of MDA and increased the content of glutathione (GSH). NADPH oxidase 4 (NOX4) expression was significantly increased in kidneys of db/db mice and in HK-2 cells after exposure to high glucose. Zingerone significantly decreased the expression of NOX4 in vivo and in vitro. Upregualtion of NOX4 significantly inhibited zingerone-induced protective effects against the cytotoxicity of high glucose. Downregulation of NOX4 was responsible for zingerone-exhibited pharmacological activities and reduction of diabetic nephropathy. Overall, zingerone is a promising therapeutic treatment to attenuate diabetic nephropathy.

KEYWORDS

Diabetic nephropathy; Inflammation; NOX4; Oxidative stress; Zingerone.

Title

Zingerone Attenuates Diabetic Nephropathy Through Inhibition of Nicotinamide Adenine Dinucleotide Phosphate Oxidase 4

Author

Yan Cui 1 , Yan Shi 1 , Yan Bao 1 , Shulong Wang 1 , Qiuju Hua 1 , Yun Liu 2

Publish date

2018 Mar