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CALYCOSIN

Definition Pharmaceutical Properties

Product Name: CALYCOSIN
CAS No.: 20575-57-9
Chemical Name: CALYCOSIN
Synonyms: Clycosin;CALYCOSIN;Calycosin-RM;CALYCOSIN(SH);Astraisoflavone;Calycosin 20575-57-9;Calycosin (Cyclosin);3'-HYDROXYFORMONONETIN;Calycosin >=98% (HPLC);Balofloxacin Impurity 8
CBNumber: CB4182878
Molecular Formula: C16H12O5
Formula Weight: 284.26
MOL File: 20575-57-9.mol

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CALYCOSIN Property

Melting point:: 245～247℃
Boiling point:: 536.8±50.0 °C(Predicted)
Density: 1.420±0.06 g/cm3(Predicted)
storage temp.: Sealed in dry,2-8°C
solubility: methanol: soluble1mg/mL, clear, colorless
pka: 6.94±0.20(Predicted)
form: powder
color: white to light yellow
InChI: InChI=1S/C16H12O5/c1-20-14-5-2-9(6-13(14)18)12-8-21-15-7-10(17)3-4-11(15)16(12)19/h2-8,17-18H,1H3
InChIKey: ZZAJQOPSWWVMBI-UHFFFAOYSA-N
SMILES: C1OC2=CC(O)=CC=C2C(=O)C=1C1=CC=C(OC)C(O)=C1

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Safety

Hazard Codes: T
Risk Statements: 25
Safety Statements: 45
RIDADR: UN 3462 6.1 / PGIII
WGK Germany: 3
HS Code: 2932996560
Hazardous Substances Data: 20575-57-9(Hazardous Substances Data)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word: Danger
Hazard statements: H301Toxic if swalloed
Precautionary statements: P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: PHL82491
Product name: Calycosin
Purity: phyproof? Reference Substance
Packaging: 10mg
Price: $587
Updated: 2025/07/31

Sigma-Aldrich

Product number: 1087472
Product name: Calycosin
Purity: United States Pharmacopeia (USP) Reference Standard
Packaging: 50mg
Price: $310
Updated: 2025/07/31

TCI Chemical

Product number: C4061
Product name: Calycosin
Packaging: 50MG
Price: $201
Updated: 2025/07/31

Cayman Chemical

Product number: 25091
Product name: Calycosin
Purity: ≥98%
Packaging: 5mg
Price: $81
Updated: 2024/03/01

Cayman Chemical

Product number: 25091
Product name: Calycosin
Purity: ≥98%
Packaging: 10mg
Price: $152
Updated: 2024/03/01

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CALYCOSIN Chemical Properties,Usage,Production

Definition

Calycosin is an O-methylated isoflavone. It can be isolated from Astragalus membranaceus Bge. var. mongholicus and Trifolium pratense L. Calycosin is a member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone which is substituted by an additional hydroxy group at the 3' position and a methoxy group at the 4' position. It has a role as a metabolite and an antioxidant. It is a member of 7-hydroxyisoflavones and a member of 4'-methoxyisoflavones. It derives from an isoflavone. It is a conjugate acid of a calycosin(1-).

Pharmaceutical Properties

The potential pharmaceutical properties of calycosin in the treatment of tumors, inflammation, stroke, and cardiovascular diseases have gained increasing attention in the recent years. The literature survey showed that calycosin exhibits promising effects for the treatment of several diseases and that these effects may be due to its isoflavonoid and phytoestrogenic properties. The effects of calycosin most likely result from its interaction with the ER receptors on the cell membrane and the modulation of the MAPK signaling pathway.
Through its effect on this pathway, calycosin can regulate several cell activities, such as apoptosis and angiogenesis, which enables its therapeutic functions.

Chemical Properties

White crystals, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from the rhizome of Astragalus membranaceus.

Uses

Calycosin is a known antioxidant that prevent redox imbalance in organisms. Also, it possesses anti-tumor, anti-inflammation and osteogenic properties; Useful as a therapeutic reagent for bone loss-associated diseases.

Definition

ChEBI: Calycosin is a member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone which is substituted by an additional hydroxy group at the 3' position and a methoxy group at the 4' position. It has a role as a metabolite and an antioxidant. It is a member of 7-hydroxyisoflavones and a member of 4'-methoxyisoflavones. It is functionally related to an isoflavone. It is a conjugate acid of a calycosin(1-).

Biological Activity

Isoflavone and phytoestrogen isolated froma traditional Chinese medicinal herb. Calycosin induces angiogenesis in HUVEC and promotes proliferation of estrogen-receptor positive cells in vivo and in vitro. Also functions as a vasorelaxant on r at thoracic aorta.

Synthesis

1131-94-8

68-12-2

108-46-3

20575-57-9

1. Resorcinol (3 mmol) and 3-hydroxy-4-methoxyphenylacetic acid (3 mmol) were dissolved in freshly distilled boron trifluoride ethyl ether solution (2 mL), heated to 85-90 °C and stirred magnetically for 6-10 hours (monitored by TLC until the raw material essentially disappears). Upon completion of the reaction, cooled to 10 °C, N,N-dimethylformamide (5 mL) was added slowly and dropwise to give mixture I. The reaction was carried out in the presence of N,N-dimethylformamide (5 mL). 2. Preparation of Vilsmeier-Haack reagent: N,N-dimethylformamide (8.1 mL) was cooled to 10 °C, phosphorus pentachloride (5 mmol) was added in batches, followed by heating to 55 °C and magnetic stirring for 1 h to give a light red or yellow mixture II. 3. Within 30 minutes, mixture II was added to mixture I in batches and stirred at room temperature for 3 hours. Subsequently, the reaction solution was poured into methanolized hydrochloric acid (0.1 mol/L, 30 mL), heated to 70 °C, kept at a constant temperature for 50 min, and then left to stand. 4. The reaction solution was concentrated by distillation under reduced pressure, washed with 150 mL of water and subsequently extracted with ethyl acetate (150 mL × 3 times). The organic phase was washed with water (150 mL x 2 times) and dried by rotary evaporation (filtered over a large amount of ethyl acetate extract to remove some impurities). 5. Some of the pigments were precipitated by suspension in a small amount of ethanol, centrifuged and filtered, and crystallized with hot ethanol, the operation being carried out under nitrogen protection. 6. Finally, the target product gross isoflavones (1.6 mmol) was obtained in 50-60% yield by silica gel column chromatography using methanol: dichloromethane = 1:35 as the unfolding agent.

in vivo

Calycosin (1-4 mg/kg, i.p., daily, 20 days) inhibits the protein expression of ERα in OVX mice at the doses of 1 mg/kg^[2].
Calycosin (7.5-30 mg/kg, i.g., daily, 3 days) has a neuroprotective effect against cerebral ischemia/reperfusion injury in adult male Sprague-Dawley rats^[3].

Animal Model:	Adult Male Sprague-Dawley Rats^[3]
Dosage:	7.5-30 mg/kg
Administration:	i.g. daily, 3 days
Result:	Improved neurological deficit and infarct volum. Reduced the content of malondialdehyde (MDA), protein carbonyl and reactive oxygen species (ROS). Increased the activities of superoxide dismutase (SOD), catalase and glutathione peroxidase (GSH-Px) in a dose-dependent manner. Inhibited the expression of 4-Hydroxy-2-nonenal (4-HNE).

References

[1] Patent: CN106749453, 2017, A. Location in patent: Paragraph 0091-0096

CALYCOSIN Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from CALYCOSIN manufacturers

Hebei Chuanghai Biotechnology Co., Ltd

Product: CALYCOSIN 20575-57-9
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 20 mt
Release date: 2024-11-07

Hebei Zhuanglai Chemical Trading Co.,Ltd

Product: Calycosin 20575-57-9
Price: US $10.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 20ton
Release date: 2024-06-07

Hebei Dangtong Import and export Co LTD

Product: CALYCOSIN 20575-57-9
Price: US $510.00-470.00/Grams
Min. Order: 10Grams
Purity: 99.99%
Supply Ability: 100Tons
Release date: 2023-03-21

20575-57-9, CALYCOSINRelated Search:

Verbascoside CALYCOSIN 7-O-GLUCOSIDE CALYCOSIN 5-HYDROXYDEQUELIN Isoflavone PSEUDOBAPTIGENIN-7-GLUCOSIDE 4H-1-Benzopyran-4-one, 3-(3,4-dimethoxyphenyl)-7-methoxy- 6-HYDROXY-7-METHOXY-3',4'-METHYLENEDIOXYISOFLAVONE OROBOL 7,4'-DIMETHYL ETHER PSEUDOBAPTIGENIN 3',4'-DIMETHOXY-7-HYDROXYISOFLAVONE PRATENSEIN FUJIKINETIN Calycosin-O-β-D-glucopyranoside CALYCOSIN(RG) AKOS 212-61 DEMETHYLACICERONE POMIFERIN-3',4'-DIMETHYL ETHER

CALYCOSIN

7,3'-DIHYDROXY-4'-METHOXYISOFLAVONE

3'-HYDROXYFORMONONETIN

3',7-DIHYDROXY-4'-METHOXYISOFLAVONE

3-(3-Hydroxy-4-methoxyphenyl)-7-hydroxy-4H-1-benzopyran-4-one

7-Hydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one

Astraisoflavone

Clycosin

CALYCOSIN(SH)

Calycosin 20575-57-9

7-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1-benzopyran-4-one

Calycosin, 98%, from Astragalus membranaceus Bunge

7-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one

Calycosin (Cyclosin)

4H-1-Benzopyran-4-one, 7-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-

Calycosin >=98% (HPLC)

3',7-Dihydroxy-4'-methoxy-isoflavone7-hydroxy-3-(3-hydroxy-4-methoxyphenyl)chromen-4-one

7,3'-dihydroxy-4'-methoxyisoflavanon-2-ene

7,5'-dihydroxy-4'-methoxyisoflavone

7-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-

7-Hydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one4H-1-Benzopyran-4-one

7-Hydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one[Cyclosin]

Calycosin-RM

Balofloxacin Impurity 8

Calycosin, 10 mM in DMSO

20575-57-9

C16H12O5

chemical reagent

pharmaceutical intermediate

phytochemical

reference standards from Chinese medicinal herbs (TCM).

standardized herbal extract

reference substance

Iso-Flavones

The group of Astralosides