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HomeProduct name listAcacetin

Acacetin

Synonym(s):4′-Methylapigenin;5,7-Dihydroxy-4′-methoxyflavone;Apigenin 4′-methyl ether;Buddleoflavonol;Linarigenin

  • CAS NO.:480-44-4
  • Empirical Formula: C16H12O5
  • Molecular Weight: 284.26
  • MDL number: MFCD00016936
  • EINECS: 207-552-3
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-12-10 11:33:04
Acacetin Structural

What is Acacetin?

Description

Acacetin is an O-methylated flavone found in various plants. It is reported to demonstrate spasmolytic, antinociceptive, anti-inflammatory, and antioxidant activity in various research models.

Chemical properties

Yellow Solid

The Uses of Acacetin

VEGF expression inhibitor and tumor angiogenesis. A flavonoid with antiaggregatory activity in human blood.

What are the applications of Application

Acacetin is a flavonoid with anti-peroxidative and anti-inflammatory properties

Definition

ChEBI: A monomethoxyflavone that is the 4'-methyl ether derivative of apigenin.

Synthesis Reference(s)

Tetrahedron Letters, 31, p. 6497, 1990 DOI: 10.1016/S0040-4039(00)97100-4

General Description

Acacetin belongs to the category of naturally occurring plant pigments called flavonoids found in vascular plants. It was first reported to be extracted from the leaves of Robinia pseuducacia. It has been used as an active component of traditional Chinese medicine Xuelianhua.

Biochem/physiol Actions

Acacetin has been noted to exhibit anti-peroxidative, anti-inflammatory, and anti-plasmodial properties. It has been posited to prevent the proliferation of Hep G2 cells, thereby causing cell apoptosis and subsequent anti-cancer action. It has antiarrhythmic properties and can be used in the treatment of Atrial fibrillation.

Enzyme inhibitor

This naturally occurring flavone (FW = 286.27 g/mol; CAS 480-44-4), also known as 5,7-dihydroxy-4’-methoxyflavone and 7-O-methylapigenin, and systematically named as 5,7-dihydroxy-2-(4-methoxyphenyl)-chromen-4- one, from the black locust Robinia pseudoacacia is the aglycon of linarin and acaciin and is biosynthesized by apigenin 4'-O-methyltransferase from S-adenosyl-methionine and 5,7,4’-trihydroxyflavone (apigenin), yielding Sadenosylhomocysteine and acacetin. The chemical synthesis of acacetin was accomplished by Robert Robinson, who was awarded the 1947 Nobel Prize in Chemistry for his work on alkaloids and organic synthesis. Target(s): glutathione S-transferase; xanthine oxidase, Ki = 0.11 μM; CYP1A; CYP1B1; glutathione-disulfide reductase; DNA topoisomerase I; [myosin light-chain] kinase; and protein-tyrosine kinase, or non-specific protein-tyrosine kinase.

Properties of Acacetin

Melting point: 260-265 °C(lit.)
Boiling point: 346.76°C (rough estimate)
Density  1.2160 (rough estimate)
refractive index  1.6200 (estimate)
storage temp.  2-8°C
solubility  DMSO (Slightly), Methanol (Very Slightly, Heated)
form  Solid
pka 6.51±0.40(Predicted)
color  Light Yellow to Green-Yellow to Dark Yellow
λmax 335nm(EtOH)(lit.)
Merck  14,13
BRN  277879
CAS DataBase Reference 480-44-4(CAS DataBase Reference)

Safety information for Acacetin

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P337+P313:IF eye irritation persists: Get medical advice/attention.

Computed Descriptors for Acacetin

InChIKey DANYIYRPLHHOCZ-UHFFFAOYSA-N

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