Calycosin

Modify Date: 2025-08-21 16:14:25

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
InChIKey ZZAJQOPSWWVMBI-UHFFFAOYSA-N
SMILES COc1ccc(-c2coc3cc(O)ccc3c2=O)cc1O
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

~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

~%

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

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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...

 CalycosinBioassay

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Name: Primary cell-based high-throughput screening assay for identification of compounds th...
Source: Johns Hopkins Ion Channel Center
Target: regulator of G-protein signaling 4 isoform 2 [Homo sapiens]
External Id: JHICC_RGS_Act_HTS
Name: Luminescence-based cell-based primary high throughput screening assay to identify ago...
Source: The Scripps Research Institute Molecular Screening Center
Target: mu-type opioid receptor isoform MOR-1 [Homo sapiens]
External Id: OPRM1-OPRD1_AG_LUMI_1536_1X%ACT PRUN
Name: QFRET-based biochemical primary high throughput screening assay to identify exosite i...
Source: The Scripps Research Institute Molecular Screening Center
Target: disintegrin and metalloproteinase domain-containing protein 17 preproprotein [Homo sapiens]
External Id: ADAM17_INH_QFRET_1536_1X%INH PRUN
Name: Fluorescence-based cell-based primary high throughput screening assay to identify ago...
Source: The Scripps Research Institute Molecular Screening Center
Target: muscarinic acetylcholine receptor M1 [Homo sapiens]
External Id: CHRM1_AG_FLUO8_1536_1X%ACT PRUN
Name: uHTS identification of small molecule activators of the adaptive arm of the Unfolded ...
Source: Burnham Center for Chemical Genomics
Target: N/A
External Id: BCCG-A405-UPR-XBP1-PrimaryAgonist-Assay
Name: High throughput fluorescence intensity-based biochemical assay to screen for small mo...
Source: University of Pittsburgh Molecular Library Screening Center
Target: furin (paired basic amino acid cleaving enzyme), isoform CRA_a [Homo sapiens]
External Id: MH080376 Biochemical HTS for Inhibitors of the Proprotein Convertase Furin.
Name: Fluorescence polarization to screen for inhibitor that competite the binding of FadD2...
Source: Broad Institute
Target: FATTY-ACID-CoA LIGASE FADD28 (FATTY-ACID-CoA SYNTHETASE)
External Id: 2147-01_Inhibitor_SinglePoint_HTS_Activity
Name: Bursicon-induced LGR2 mediated cAMP production in LGR-2/CRE6x-Luciferase co-transfect...
Source: Broad Institute
Target: N/A
External Id: Bursicon-induced LGR2 mediated cAMP production in LGR-2/CRE6x-Luciferase co-transfected HEK293 cells Inhibition - 7011-01_Antagonist_SinglePoint_HTS_Activity
Name: Cytotoxicity against human PANC1 cells in nutrient deprived medium after 24 hrs
Source: ChEMBL
Target: PANC-1
External Id: CHEMBL928450
Name: Fluorescence-based cell-based primary high throughput screening assay to identify pos...
Source: The Scripps Research Institute Molecular Screening Center
Target: muscarinic acetylcholine receptor M1 [Homo sapiens]
External Id: CHRM1_PAM_FLUO8_1536_1X%ACT PRUN
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 Synonyms

7,5'-dihydroxy-4'-methoxyisoflavone
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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