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Acacetin

$143

  • Brand : BIOFRON

  • Catalogue Number : BF-A2002

  • Specification : 98%

  • CAS number : 480-44-4

  • Formula : C16H12O5

  • Molecular Weight : 284.26

  • PUBCHEM ID : 5280442

  • Volume : 20mg

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Catalogue Number

BF-A2002

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

284.26

Appearance

Brown needle crystal

Botanical Source

Mentha canadensis,Cirsium japonicum,Eleutherococcus senticosus,Aquilaria sinensis,Carthamus tinctorius

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

SMILES

COC1=CC=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)O)O

Synonyms

Linarigenin/5,7-Dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one/5,7-Dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one/Acacetin/5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one/5,7-Dihydroxy-4'-methoxyflavone/Apigenin-4'-methyl Ether/4'-O-Methylapigenin/Buddleoflavonol/4'-Methoxyapigenin/4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-methoxyphenyl)-/Apigenin 4'-methyl ether

IUPAC Name

5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one

Density

1.4±0.1 g/cm3

Solubility

DMF

Flash Point

198.3±23.6 °C

Boiling Point

518.6±50.0 °C at 760 mmHg

Melting Point

260-265 °C(lit.)

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2941900000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:480-44-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31142008

Abstract

To probe the effect of 3′,8″-dimerization on antioxidant flavonoids, acacetin and its 3′,8″-dimer isoginkgetin were comparatively analyzed using three antioxidant assays, namely, the ·O2- scavenging assay, the Cu2+ reducing assay, and the 2,2′-azino bis(3-ethylbenzothiazolin-6-sulfonic acid) radical scavenging assay. In these assays, acacetin had consistently higher IC50 values than isoginkgetin. Subsequently, the acacetin was incubated with 4-methoxy-2,2,6,6-tetramethylpiperidine-1-oxy radicals (4-methoxy-TEMPO) and then analyzed by ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UHPLC-ESI-Q-TOF-MS) technology. The results of the UHPLC-ESI-Q-TOF-MS analysis suggested the presence of a dimer with m/z 565, 550, 413, 389, 374, 345, 330, and 283 peaks. By comparison, standard isoginkgetin yielded peaks at m/z 565, 533, 518, 489, 401, 389, 374, and 151 in the mass spectra. Based on these experimental data, MS interpretation, and the relevant literature, we concluded that isoginkgetin had higher electron transfer potential than its monomer because of the 3′,8″-dimerization. Additionally, acacetin can produce a dimer during its antioxidant process; however, the dimer is not isoginkgetin.

KEYWORDS

3′,8″-dimerization; acacetin; antioxidant; isoginkgetin; radical adduct formation

Title

3',8″-Dimerization Enhances the Antioxidant Capacity of Flavonoids: Evidence from Acacetin and Isoginkgetin.

Author

Li X1,2, Ouyang X3,4, Cai R5,6, Chen D7,8.

Publish date

2019 May 28

PMID

31066474

Abstract

Aacacetin, a plant flavone has shown antitumor efficacy recently. However, its associated mechanisms are poorly known. We hypothesized that the muscarinic M3 receptor (M3 R), which is highly expressed in some cancer tissue, is related to the antitumor effect of acacetin in head and neck squamous cell carcinoma (HNSCC) cells. Our results showed that 12.5- to 200-μM acacetin inhibited cell viability in dose- and time-dependent manners in HNSCC cells, but a relative higher concentration was needed for oral adenoid cystic carcinoma cells. M3 R expression level was higher in HNSCC cells than that in adenoid cystic carcinoma cells. Flow cytometry and electron microscopy confirmed acacetin-induced cell apoptosis in 22B cells, a HNSCC cell line. Acacetin promoted mitochondrial cytochrome c release and caspase 9, 3 processing. Knocking down of M3 R expression by specific siRNA significantly prevented the acacetin-induced cell viability damage, cell apoptosis, and caspase 3 activation. Besides, M3 R was also involved in acacetin-induced elevation of reactive oxygen species and intracellular calcium ([Ca2+ ]i ). These data indicate that acacetin-induced cell apoptosis in HNSCC cells may through M3 R related calcium signaling and caspase 3 activation. Acacetin is a potent natural antitumor reagent especially for the tumor cells, which highly expressed M3 R.

© 2019 John Wiley & Sons, Ltd.

KEYWORDS

acacetin; caspase; cell apoptosis; head and neck squamous cell carcinoma; muscarinic M3 receptor

Title

Acacetin-induced cell apoptosis in head and neck squamous cell carcinoma cells: Evidence for the role of muscarinic M3 receptor.

Author

Sun F1,2, Li D1, Wang C1, Peng C1, Zheng H3, Wang X1.

Publish date

2019 May

PMID

31025561

Abstract

Acacetin, a dietary component, is abundant in acacia honey and has superior anticancer activities. To date, no research on the metabolism of acacetin has been reported. In the current research, an online detection strategy of ultra-high-performance liquid chromatography connected to a quadrupole time-of-flight mass spectrometer (UHPLC-Q-TOF-MS/MS) was utilized for metabolite identification in vivo (rat plasma, bile, urine, and feces) and in vitro (rat liver microsomes). A total of 31 metabolites were structurally characterized in rats, and 25 metabolites were detected in rat liver microsomes, among which, 4 metabolites were compared with standards. Oxidation, the loss of CH2, reduction, hydrolysis, glucuronide conjugation, sulfate conjugation, methylation, and N-acetylation were the main metabolic pathways of acacetin. This study is the first to characterize acacetin metabolites in vivo and in vitro, and the results of this study offer novel and valuable evidence for a comprehensive understanding of the safety and efficacy of acacetin.

KEYWORDS

UHPLC-Q-TOF-MS/MS; acacetin; in vivo and in vitro; metabolism

Title

A Systematic Study of the Metabolites of Dietary Acacetin in Vivo and in Vitro Based on UHPLC-Q-TOF-MS/MS Analysis.

Author

Yin J1, Ma Y2, Liang C1, Gao J2, Wang H1, Zhang L1.

Publish date

2019 May 15


Description :

1) Natural acacetin was a 4.0-fold and 5.5-fold more potent inhibitor of BACE-1 than oleanolic acid and maslinic acid, respectively.[1]2) Acacetin significantly suppressed the photoreceptor collapse. [1]3) Acacetin significantly reduces the Aβ levels by interfering with human APP proteolytic processing and BACE-1 expression. [1]4) Acacetin inhibited the generation of the APP-CTF by affecting APP cleavage. [1]5) Acacetin prolongs lifespan of significantly in the dose dependent manner. Acacetin(25 uM) had the greatest effect on longevity, extending mean lifespan significantly by 27.31% at 25 uM concentration