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20575-57-9

20575-57-9 structure
20575-57-9 structure
  • Name: Calycosin
  • Chemical Name: calycosin
  • CAS Number: 20575-57-9
  • Molecular Formula: C16H12O5
  • Molecular Weight: 284.263
  • Catalog: Natural product Flavonoids
  • Create Date: 2018-06-25 00:17:34
  • Modify Date: 2024-01-03 16:18:43
  • Calycosin (Cyclosin) is a natural active compound with anti-oxidative and anti-inflammation activity.IC50 value:Target: in vitro: calycosin had obvious anti-proliferation effects on SKOV3 cells in a dose- and time-dependent manner. calycosin up-regulated the Bax/Bcl-2 ratio and cleaved caspase-3, cleaved caspase-9 expression in a dose-dependent manner. In summary, calycosin might exert anti-growth and induce-apoptosis activity against ovarian cancer SKOV3 cells through activating caspases and Bcl-2 family proteins, therefore presenting as a promising therapeutic agent for the treatment of ovarian cancer [1]. Both calycosin and genistein inhibited proliferation and induced apoptosis in MCF-7 breast cancer cells, especially after treatment with calycosin. Treatment of MCF-7 cells with calycosin or genistein resulted in decreased phosphorylation of Akt, and decreased expression of its downstream target, HOTAIR [2]. incubation of calycosin resulted in enhanced expression ERβ in MCF-7 and T-47D cells, rather than MDA-231 and MDA-435 cells. Moreover, with the upregulation of ERβ, successive changes in downstream signaling pathways were found, including inactivation of insulin-like growth factor 1 receptor (IGF-1R), then stimulation of p38 MAPK and suppression of the serine/threonine kinase (Akt), and finally poly(ADP-ribose) polymerase 1 (PARP-1) cleavage [3].in vivo: calycosin stimulated a dramatic increase in uterine weight and downregulated the level of ERα protein in OVX mice [4].

Name calycosin
Synonyms 7,5'-dihydroxy-4'-methoxyisoflavone
4H-1-Benzopyran-4-one, 7-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-
7,3'-dihydroxy-4'-methoxyisoflavone
7-Hydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one
7-hydroxy-3-(3-hydroxy-4-methoxyphenyl)chromen-4-one
3'-hydroxyformononetin
3',7-Dihydroxy-4'-methoxy-isoflavone
Calycosin
3',7-dihydroxy-4'-methoxyisoflavone
7,3'-dihydroxy-4'-methoxyisoflavanon-2-ene
Description Calycosin (Cyclosin) is a natural active compound with anti-oxidative and anti-inflammation activity.IC50 value:Target: in vitro: calycosin had obvious anti-proliferation effects on SKOV3 cells in a dose- and time-dependent manner. calycosin up-regulated the Bax/Bcl-2 ratio and cleaved caspase-3, cleaved caspase-9 expression in a dose-dependent manner. In summary, calycosin might exert anti-growth and induce-apoptosis activity against ovarian cancer SKOV3 cells through activating caspases and Bcl-2 family proteins, therefore presenting as a promising therapeutic agent for the treatment of ovarian cancer [1]. Both calycosin and genistein inhibited proliferation and induced apoptosis in MCF-7 breast cancer cells, especially after treatment with calycosin. Treatment of MCF-7 cells with calycosin or genistein resulted in decreased phosphorylation of Akt, and decreased expression of its downstream target, HOTAIR [2]. incubation of calycosin resulted in enhanced expression ERβ in MCF-7 and T-47D cells, rather than MDA-231 and MDA-435 cells. Moreover, with the upregulation of ERβ, successive changes in downstream signaling pathways were found, including inactivation of insulin-like growth factor 1 receptor (IGF-1R), then stimulation of p38 MAPK and suppression of the serine/threonine kinase (Akt), and finally poly(ADP-ribose) polymerase 1 (PARP-1) cleavage [3].in vivo: calycosin stimulated a dramatic increase in uterine weight and downregulated the level of ERα protein in OVX mice [4].
Related Catalog
References

[1]. Zhou Y, et al. Calycosin induces apoptosis in human ovarian cancer SKOV3 cells by activating caspases and Bcl-2 family proteins. Tumour Biol. 2015 Feb 12.

[2]. Chen J, et al. Calycosin and genistein induce apoptosis by inactivation of HOTAIR/p-Akt signaling pathway in human breast cancer MCF-7 cells. Cell Physiol Biochem. 2015;35(2):722-8.

[3]. Chen J, et al. Calycosin suppresses breast cancer cell growth via ERβ-dependent regulation of IGF-1R, p38 MAPK and PI3K/Akt pathways. PLoS One. 2014 Mar 11;9(3):e91245.

[4]. Chen J, et al. Calycosin promotes proliferation of estrogen receptor-positive cells via estrogen receptors and ERK1/2 activation in vitro and in vivo. Cancer Lett. 2011 Sep 28;308(2):144-51.

Density 1.4±0.1 g/cm3
Boiling Point 536.8±50.0 °C at 760 mmHg
Molecular Formula C16H12O5
Molecular Weight 284.263
Flash Point 205.7±23.6 °C
Exact Mass 284.068481
PSA 79.90000
LogP 2.41
Appearance white to light yellow
Vapour Pressure 0.0±1.5 mmHg at 25°C
Index of Refraction 1.669
Storage condition 2-8°C
Water Solubility methanol: soluble1mg/mL, clear, colorless
Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301
Precautionary Statements P301 + P310
Hazard Codes T
Risk Phrases 25
Safety Phrases 45
RIDADR UN 3462 6.1 / PGIII
HS Code 2914509090

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20575-57-9 structure

20575-57-9

Literature: Bhandari, Prabha; Crombie, Leslie; Daniels, Peter; Holden, Ian; Bruggen, Nicholas Van; Whiting, Donald A. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992 , # 7 p. 839 - 850

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20575-57-9 structure

20575-57-9

Detail
Literature: Journal of Agricultural and Food Chemistry, , vol. 52, # 21 p. 6623 - 6632
HS Code 2914509090
Summary HS:2914509090 other ketones with other oxygen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%