Calycosin

Modify Date: 2024-01-03 16:18:43

Calycosin Structure
Calycosin structure
 Common Name Calycosin
CAS Number 20575-57-9 Molecular Weight 284.263
Density 1.4±0.1 g/cm3 Boiling Point 536.8±50.0 °C at 760 mmHg
Molecular Formula C16H12O5 Melting Point N/A
MSDS Chinese USA Flash Point 205.7±23.6 °C
Symbol GHS06
GHS06		 Signal Word Danger

 Use of Calycosin


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].

 Names

Name calycosin
Synonym More Synonyms

 Calycosin Biological Activity

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.

 Chemical & Physical Properties

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 of Characters 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

 Safety Information

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

 Synthetic Route

1-(2,4-dihydroxyphenyl)-2-(3-hydroxy-4-methoxyphenyl)ethanone structure

1-(2,4-dihydrox...

CAS#:36754-72-0

Triethyl orthoformate structure

Triethyl orthof...

CAS#:122-51-0

~62%

Calycosin Structure

Calycosin

CAS#: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
Formononetin structure

Formononetin

CAS#:485-72-3

~%

6,7-DIHYDROXY-4'-METHOXYISOFLAVONE structure

6,7-DIHYDROXY-4...

CAS#:897-46-1

7,8-Dihydroxy-4'-methoxy isoflavone (Retusin) structure

7,8-Dihydroxy-4...

CAS#:37816-19-6

Calycosin Structure

Calycosin

CAS#:20575-57-9

Detail
Literature: Journal of Agricultural and Food Chemistry, , vol. 52, # 21 p. 6623 - 6632

 Customs

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%

 Articles9

More Articles
Thermal stability of kudzu root (Pueraria Radix) isoflavones as additives to beef patties.

J. Food Sci. Technol. 52(3) , 1578-85, (2015)

Kudzu root, Pueraria radix, extracts are a rich source of isoflavones. This study investigates the thermal stability of Pueraria radix extracts as a natural nutraceutical supplement in beef patties. T...

Calycosin orchestrates the functions of Danggui Buxue Tang, a Chinese herbal decoction composing of Astragali Radix and Angelica Sinensis Radix: An evaluation by using calycosin-knock out herbal extract.

J. Ethnopharmacol. 168 , 150-7, (2015)

Danggui Buxue Tang (DBT) is a classical Chinese herbal decoction containing two herbs, Astragali Radix (AR) and Angelicae Sinensis Radix (ASR), which serves as dietary supplement for treating women me...

Protective effects of calycosin against CCl4-induced liver injury with activation of FXR and STAT3 in mice.

Pharm. Res. 32(2) , 538-48, (2015)

Investigating the hepatoprotective effect of calycosin against acute liver injury in association with FXR activation and STAT3 phosphorylation.The acute liver injury model was established by intraperi...

 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
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