491-54-3 Usage
Chemical Properties
Yellow powder
Uses
Kaempferide is a flavonoid that maintains anti-radical and anti-oxidant capabilities, as well as anti-tumour possibilities. Impurity of Icaritin (I163700).
Definition
ChEBI: A monomethoxyflavone that is the 4'-O-methyl derivative of kaempferol.
Biological Activity
the effects of phytoestrogens have been studied in the hypothalamic-pituitary-gonadal axis and various non-gonadal targets. epidemiologic and experimental evidence indicates a protective effect of phytoestrogens also in colorectal cancer. the mechanism through which estrogenic molecules control colorectal cancer tumorigenesis could possibly involve estrogen receptor β, which is the predominantly expressed estrogen receptor subtype in colon mucosa.
in vitro
kaempferide triglycoside proved to inhibit the proliferation of native and estrogen receptor β overexpressing colon cancer cells via a mechanism not mediated by ligand binding dependent estrogen receptor activation. it affected hct8 cell cycle progression through increasing the g0/g1 cell fraction and in estrogen receptor β overexpressing cells increased two antioxidant enzymes [1].
in vivo
the aim of one previous study was to evaluate the effect of kaempferol on tissue lipid peroxidation and antioxidant status in 1,2-dimethyl hydrazine induced colorectal cancer in male wistar rats and to compare its efficacy with irinotecan. this study revealed that kaempferol could be safely used as a chemopreventive agent in colorectal cancer [2].
references
[1] martineti v, tognarini i, azzari c, carbonell sala s, clematis f, dolci m, lanzotti v, tonelli f, brandi ml, curir p. inhibition of in vitro growth and arrest in the g0/g1 phase of hct8 line human colon cancer cells by kaempferide triglycoside from dianthus caryophyllus. phytother res. 2010 sep;24(9):1302-8. [2] nirmala p, ramanathan m. effect of kaempferol on lipid peroxidation and antioxidant status in 1,2-dimethyl hydrazine induced colorectal carcinoma in rats. eur j pharmacol. 2011 mar 1;654(1):75-9.
Check Digit Verification of cas no
The CAS Registry Mumber 491-54-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,9 and 1 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 491-54:
(5*4)+(4*9)+(3*1)+(2*5)+(1*4)=73
73 % 10 = 3
So 491-54-3 is a valid CAS Registry Number.
491-54-3Relevant articles and documents
Flavonol glycosides from Costus spicatus
Da Silva, Bernadete P.,Bernardo, Robson R.,Parente, Jose P.
, p. 87 - 92 (2000)
Two flavonol diglycosides, tamarixetin 3-O-neohesperidoside, kaempferide 3-O-neohesperidoside and the known quercetin 3-O-neohesperidoside, together with six other known flavonoids were isolated from the leaves of Costus spicatus and their structures were elucidated by a combination of spectroscopic and chemical methods. The flavonol diglycosides were evaluated for inhibitory activity of nitric oxide production by activated macrophages (Fig. 1).
Synthesis and Biological Evaluation of 4-Substituted Kaempfer-3-ols
Kim, Sugyeom,Lannigan, Deborah A.,Li, Yu,Lin, Lin,O'Doherty, George A.,Sayasith, Peyton R.,Tarr, Ariel T.,Wright, Eric B.,Yasmin, Sharia
, p. 4279 - 4288 (2020/04/09)
The synthesis of two series of five kaempfer-3-ols was described. The first set all have a C-3 hydroxyl group and the second has a carboxymethoxy ether at the C-3 position. Both series have variable substitution at the C-4 position (i.e., OH, Cl, F, H, OMe). Both kaempferols and carboxymethoxy ethers were evaluated for their ability to inhibit ribosomal s6 kinase (RSK) activity and cancer cell proliferation.
Selective methylation of kaempferol via benzylation and deacetylation of kaempferol acetates
Mei, Qinggang,Wang, Chun,Yuan, Weicheng,Zhang, Guolin
, p. 288 - 293 (2015/03/31)
A strategy for selective mono-, di- and tri-O-methylation of kaempferol, predominantly on the basis of selective benzylation and controllable deacetylation of kaempferol acetates, was developed. From the selective deacetylation and benzylation of kaempferol tetraacetate (1), 3,4′,5,-tri-O-acetylkaempferol (2) and 7-O-benzyl-3,4′5,-tri-O-acetylkaempferol (8) were obtained, respectively. By controllable deacetylation and followed selective or direct methylation of these two intermediates, eight O-methylated kaempferols were prepared with 51-77% total yields from kaempferol.
