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A8206

Sigma-Aldrich

Acacetin

Synonym(s):

4′-Methylapigenin, 5,7-Dihydroxy-4′-methoxyflavone, Apigenin 4′-methyl ether, Buddleoflavonol, Linarigenin

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About This Item

Empirical Formula (Hill Notation):
C16H12O5
CAS Number:
480-44-4
Molecular Weight:
284.26
Beilstein/REAXYS Number:
277879
EC Number:
207-552-3
MDL number:
MFCD00016936
UNSPSC Code:
12352200
PubChem Substance ID:
329770950

mp

260-265 °C (lit.)

storage temp.

2-8°C

SMILES string

COc1ccc(cc1)C2=CC(=O)c3c(O)cc(O)cc3O2

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

InChI key

DANYIYRPLHHOCZ-UHFFFAOYSA-N

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Biochem/physiol Actions

A flavonoid derivative possessing antioxidant properties.[1] Induces cell cycle arrest and apoptosis in a time- and dose-dependent manner in several cancer cell lines in vitro.
Flavonoid with anti-peroxidative and anti-inflammatory properties. Used in traditional Chinese medicine.
Flavonoid with anti-peroxidative and anti-inflammatory properties. Used in traditional Chinese medicine. It has been recognized as an antiproliferative agent on cancer cell lines by inducing apoptosis and blocking cell cycle progression in the G1 phase.

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Description
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Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
014K4091
075H4003
064K4029
043K4087

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M R Cholbi et al.
Experientia, 47(2), 195-199 (1991-02-15)
The antiperoxidative effects of 35 phenolic compounds, most of them belonging to the flavonoid class, were investigated using CCl4-induced peroxidation of rat liver microsomes. This system was rather insensitive to gallic acid, methyl gallate and ellagic acid. Nevertheless it was
Y T Chen et al.
Free radical biology & medicine, 9(1), 19-21 (1990-01-01)
The superoxide anions scavenging activity and antioxidation of seven flavonoids--quercetin, rutin, morin, acacetin, hispidulin, hesperidin, and naringin--were studied. The superoxide anions were generated in a phenazin methosulphate-NADH system and were assayed by reduction of nitroblue tetrazolium. The scavenging activity ranked:
Ya-Ling Hsu et al.
Cancer letters, 212(1), 53-60 (2004-07-13)
In this study, we examined acacetin (5,7-dihydroxy-4'-methoxyflavone), a flavonoid compound, for its effect on proliferation in human non-small cell lung cancer A549 cells. The results first reported that acacetin not only inhibited A549 cell proliferation but also induced apoptosis and
K Zhang et al.
Biochemical pharmacology, 47(11), 2063-2068 (1994-06-01)
Several novel naturally occurring flavonoids and other polyphenols exerted varying degrees of concentration-dependent inhibition on uncharacterized rat liver glutathione S-transferase (EC 2.5.1.18, GST) isoforms. The order of inhibitory potencies of the five most potent polyphenols was tannic acid > 2-hydroxyl
Jidan Liu et al.
Carbohydrate research, 357, 41-46 (2012-06-27)
Apigenin-7-O-β-D-glycosides 1-8 and acacetin-7-O-β-D-glycosides 9-16 were semisynthesized from 4'-O-benzyl apigenin 17 and acacetin 18 by glycosidation and deprotection with the corresponding α-acetylglycosyl bromide, respectively. Compounds 17 and 18 were prepared by iodination followed by base-induced elimination, 4'-O-benzylation, or 4'-O-methylation and
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