| Identification | More | [Name]
Acacetin | [CAS]
480-44-4 | [Synonyms]
5,7-DIHYDROXY-4'-METHOXYFLAVONE
ACACETIN
LINARIGENIN
METHYL-4'-APIGENIN
5,7-dihydroxy-2-(4-methoxyphenyl)-4h-1-benzopyran-4-on
5,7-dihydroxy-4’-methoxy-flavon
5,7-dioxy-4’-methoxyflavone
acacetine
apisenin4’-methylether
buddleoflavonol
5,7-dihydroxy-2-(4-methoxyphenyl)-4-benzopyrone
Abietic
ACACETIN(METHYL-4'-APIGENIN)(RG)
5,7-DIHYDROXY-2-(4-METHOXYPHENOL)-1-BENZOPYRAN-4-ONE
1-BENZOPYRAN-4-ONE,5,7-DIHYDROXY-2-(4-METHOXYPHENOL)-
ACACETIN hplc
ACACETIN WITH HPLC
4'-O-Methylapigenin
5,7-Dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one
Linarisenin | [EINECS(EC#)]
207-552-3 | [Molecular Formula]
C16H12O5 | [MDL Number]
MFCD00016936 | [Molecular Weight]
284.26 | [MOL File]
480-44-4.mol |
| Chemical Properties | Back Directory | [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 ]
13,13 | [BRN ]
277879 | [Major Application]
metabolomics
vitamins, nutraceuticals, and natural products | [InChI]
1S/C16H12O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-8,17-18H,1H3 | [InChIKey]
DANYIYRPLHHOCZ-UHFFFAOYSA-N | [SMILES]
COc1ccc(cc1)C2=CC(=O)c3c(O)cc(O)cc3O2 || COc1ccc(cc1)C2=CC(=O)c3c(O)cc(O)cc3O2 | [LogP]
2.443 (est) | [CAS DataBase Reference]
480-44-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P280-P305+P351+P338-P337+P313-P261 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
DJ3002000
| [F ]
3-8-10 | [HS Code ]
29329990 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [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.1,2 | [Chemical Properties]
Yellow Solid | [Uses]
VEGF expression inhibitor and tumor angiogenesis. A flavonoid with antiaggregatory activity in human blood. | [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. | [References]
[1] SYLWIA ZIELI?SKA Adam M. Phytochemistry and bioactivity of aromatic and medicinal plants from the genus Agastache (Lamiaceae)[J]. Phytochemistry Reviews, 2014, 13 2: 391-416. DOI: 10.1007/s11101-014-9349-1
[2] SARAVANA KUMAR JAGANATHAN M M. Antiproliferative effects of honey and of its polyphenols: a review.[J]. Journal of Biomedicine and Biotechnology, 2009, 2009: 830616. DOI: 10.1155/2009/830616 |
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