Tanshinone IIA

Product Name: Tanshinone IIA
CAS No.: 568-72-9
Chemical Name: Tanshinone IIA
Synonyms: Tanshinone 2A;tanshiones;SweetOrange;Tanshine II;Tanshinone B;ANSHINONE ⅡA;Tanshionesiia;TANSHINONE A;2A tanshinone;ATanshinoneⅡA
CBNumber: CB5705548
Molecular Formula: C19H18O3
Formula Weight: 294.34
MOL File: 568-72-9.mol

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Tanshinone IIA Property

Melting point:: 196.0 to 200.0 °C
Boiling point:: 480.7±44.0 °C(Predicted)
Density: 1.209±0.06 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: methanol: soluble5mg/mL, clear, red-orange to red
form: powder, red
color: Orange
Stability:: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
InChIKey: HYXITZLLTYIPOF-UHFFFAOYSA-N
LogP: 4.925 (est)
CAS DataBase Reference: 568-72-9(CAS DataBase Reference)

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Safety

Safety Statements: 24/25
WGK Germany: 3
RTECS: SF8282695
HS Code: 29321900
Hazardous Substances Data: 568-72-9(Hazardous Substances Data)

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: PHL89320
Product name: Tanshinone IIA
Purity: phyproof? Reference Substance
Packaging: 10MG
Price: $229
Updated: 2024/03/01

Sigma-Aldrich

Product number: 1643339
Product name: Tanshinone IIA
Purity: United States Pharmacopeia (USP) Reference Standard
Packaging: 20mg
Price: $263
Updated: 2024/03/01

Sigma-Aldrich

Product number: 51704
Product name: Tanshinone IIA
Purity: analytical standard
Packaging: 10mg
Price: $173
Updated: 2022/05/15

TCI Chemical

Product number: T2987
Product name: Tanshinone IIA
Purity: >97.0%(HPLC)
Packaging: 10mg
Price: $145
Updated: 2024/03/01

TCI Chemical

Product number: T2987
Product name: Tanshinone IIA
Purity: >97.0%(HPLC)
Packaging: 50mg
Price: $494
Updated: 2024/03/01

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Tanshinone IIA Chemical Properties,Usage,Production

Description

Tanshinone IIA mainly exists in the roots of Salvia miltiorrhiza Bge. Traditional Chinese medicine Danshen, slightly cold and bitter, is often used for activating blood circulation and eliminating stasis in Chinese medicine. It can also promote blood circulation, open the energy channels, calm the heart, cool the blood, relieve swelling, remove twinge in the heart and stomach, and remove carbuncle and erysipelas. It is classified as high grade in Shen Nong’s Herbal Classic. It has been used as a traditional Chinese medicine in clinical practice for thousands of years. And it is not only recorded in the leading medical works through the ages but also in CP and USP.

Description

Tanshinone IIA (TSA) is a major lipophilic component of extracts from the root of S. miltiorrhiza, used widely in Chinese herbal medicine. It has anti-inflammatory activity, inhibiting production of TNF-α, IL-1β, IL-6, NO, INFγ, and expression of iNOS, and IL-12. It blocks human aortic smooth muscle cell migration, inhibits MMP-9 activity, and interferes with PI3K/Akt and ERK1/2 signaling pathways. It is cytotoxic to various cancer cells including A549 lung cancer cells and leukemia cells.Reduction of TSA by NAD(P)H:quinone oxidoreductase (NQO1) generates an unstable intermediate resulting in reactive oxygenase species-mediated apoptotic cell death.

Chemical Properties

Orange powder

Physical properties

Appearance: brick-red crystalline powder. Melting point: 209–210?°C. Solubility: absorbs moisture easily, very soluble in hot water, slightly soluble in methanol or ethanol, and practically insoluble in chloroform

History

The study of the chemical composition of Salvia miltiorrhiza began in the 1930s. Japanese scholars first extracted three kinds of liposoluble components from Danshen. They are tanshinones I, II, and III.

Uses

Tanshinone IIA is a derivative of Tanshinone and acts as a potential inhibitor of tumor growth in vivo. Also maintains vasodilating activity in vivo.

Uses

antineoplastic, bone resorption inhibitor, antiproliferative, apoptosis inducer

Definition

ChEBI: 1,6,6-trimethyl-8,9-dihydro-7H-naphtho[1,2-g]benzofuran-10,11-dione is an abietane diterpenoid.

Synthesis Reference(s)

Journal of the American Chemical Society, 111, p. 1522, 1989 DOI: 10.1021/ja00186a070

Biochem/physiol Actions

Phenanthrenequinone constituent of Chinese medicinal herb Danshen (Salvia miltiorrhiza). Anti-inflammatory. Antioxidant. Cytotoxic against a variety of cell lines, inlcuding human glioma cells.

Pharmacology

Long-term researches show that tanshinone exhibits a variety of pharmacological effects, such as the protection of the cardiovascular system, anti-infective effects, and antioxidant effects. As for the domestic pharmacological study of tanshinone IIA, it was first started in the Shanghai Institute of Chinese Medicine. Professor Ding Guangsheng discussed the cardiovascular effects of tanshinone IIA.?He found that intraperitoneal injection of tanshinone IIA sodium sulfonate (200?mg/kg) significantly prolonged the survival time of mice under hypoxia atmosphere, and an increase in cardiac output was observed in a dog under anesthesia with a one-time intravenous injection of 20? mg/kg . In recent years, the mechanism of tanshinone IIA is increasingly brought to further research. Tanshinone IIA can increase the activity of superoxide dismutase (SOD) and interfere with the pathological process of many diseases, especially in cardiovascular diseases. It can attenuate the damages from the reactive oxygen species to vascular endothelial cells, lower the risk of atherosclerosis, and reduce the formation of atheromatous plaque. tumor cells and the expression of various genes connected with the proliferation, differentiation, and apoptosis of tumor cells. It may also have something to do with the inhibition of telomerase activity in tumor cells, changes in antigen expression on tumor cell surface, etc.

Clinical Use

Tanshinone IIA is a diterpenoid quinone liposoluble ingredient of high content, and its chemical structure is the most representative in Danshen. In addition to tanshinone IIA sodium sulfonate, there are a variety of preparations of Salvia common ketone used clinically, such as tanshinone tablets, tanshinone capsules, tanshinone injection, Danshen Shuxin capsule, compound Danshen soft capsules, and compound Danshen particles.

Cytotoxicity

IC50 (μg/mL): 0.59 (A549), 0.81 (TOV-21G) and 1.9 (MIAPaCa-2), NS (MV-3)(Chang et al. 2013; Fronza et al. 2011).
IC50 (μg/mL): 2.97 (HeLa), 2.71 (KB-3-1),>2.94 (NCI-H460), 2.62 (PC3), 2.94(MCF-7), 1.62 (K562)(Wu et al. 2014)

References

1) Kang et al. (2000), Inhibition of interleukin-12 and interferon-gamma production in immune cells by tanshinones from Salvia miltiorrhiza; Immunopharmacology, 49 355 2) Sung et al. (1999), Tanshinone IIA, an ingredient of Salvia miltiorrhiza BUNGE, induces apoptosis in human leukemia cell lines through the activation of caspase-3; Exp. Mol. Med., 31 174 3) Park et al. (1999), Suppression of AP-1 Activity by Tanshinone and Cancer Cell Growth Inhibition; Bull. Korean Chem. Soc., 20 925

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Raw materials

Preparation Products

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View Lastest Price from Tanshinone IIA manufacturers

Hebei Mujin Biotechnology Co.,Ltd

Product: Tanshinone IIA 568-72-9
Price: US $0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 50000KG/month
Release date: 2023-08-28

Hebei Mujin Biotechnology Co.,Ltd

Product: Tanshinone IIA 568-72-9
Price: US $0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 50000KG/month
Release date: 2024-08-05

WUHAN FORTUNA CHEMICAL CO., LTD

Product: Tanshinone IIA 568-72-9
Price: US $0.00/KG
Min. Order: 1KG
Purity: 98%min
Supply Ability: 30tons/month
Release date: 2023-02-02

568-72-9, Tanshinone IIARelated Search:

Tanshinone I D-(-)-Salicin Icariin Matrine TanshinoneIIA Salvia Root P.E Tanshinone IIA 20% TanshinoneIIB Sodium Tanshinone IIA 2-FURAN-2-YL-BENZALDEHYDE 2,5-DIMETHYLPHENYLACETONE trimethylcumene 2-(2,5-DIMETHYLPHENYL)ACETALDEHYDE 1-(5,6,7,8-TETRAHYDRO-NAPHTHALEN-1-YL)-ETHANONE Ethanone, 1-(3-furanyl)- (9CI) 1,5-DIMETHYL-1,2,3,4-TETRAHYDRONAPHTHALENE 3-Acetyl-2,4-dimethylfuran DANSHEN TANSHINONE STANDARDS KIT 5MG Tanshinone IIA

AKOS NCG1-0066

3,8,8-TRIMETHYL-8,9,10,11-TETRAHYDROPHENANTHRO[1,2-B]FURAN-1,2-DIONE

TANSHINONE IIA 98+%

Tanshinone IIA, 97%, from Salvia miltiorrhiza Bunge

1,6,6-TRIMETHYL-6,7,8,9-TETRAHYDRO-PHENANTHRO[1,2-B]FURAN-10,11-DIONE

TANSHINONE IIA

TANSHINONES IIA

tanshiones

Tanshionesiia

TANSHINONE IIA 98%

TANSHINONE IIA 98+% HPLC

TANSHION P.E 20%

SweetOrange

TANSHINONE A

Tanshinone 2A

1,6,6-trimethyl-2,7,8,9-tetrahydro-1H-naphtho[1,2-g]benzofuran-10,11-dione

1,6,6-trimethyl-8,9-dihydro-7H-naphtho[1,2-g]benzofuran-10,11-dione

TANSHINONE IIA(P)

Salvia quinone A

Phenanthro[1,2-b]furan-10,11-dione,6,7,8,9-

tetrahydro-1,6,6-trimethyl-

6,7,8,9-Tetrahydro-1,6,6-trimethylphenanthro[1,2-b]furan-10,11-dione

Dan Shen ketone

Sodium Tanshinone IIA Silate

Tanshine II

Stone lotus leaf extract

Tanshinone II A (Salvia quinone A)

Tanshinone IIA (Tanshinone B)

Phenanthro [1, 2-b]furan-10, 11-dione, 6, 7, 8, 9-tetrahydro-1, 6, 6-triMethy

Tanshinone ⅡA, froM Salvia Miltiorrhiza

Tanshinone IIA (20 mg)

Tanshinone B

ANSHINONE ⅡA

Tanshinonel IIA

Tanshinone IIA 568-72-9

Tanshinone IIA, 97%, from Salvia miltiorrhiza

Tanshinone IIa CRS

2A tanshinone

Tanshinone IIA (Dan Shen ketone)

ATanshinoneⅡA

Tanshinone IIA (1643339)

Tanshinone IIA (7CI)

Tanshinone IIA-RM

Abametapir Impurity 26

Salvia Miltiorrhiza Extract, Danshen Root Extract Tanshinone IIA

568-72-9

8568-72-9

C19H18O3

Inhibitors

chemical reagent

pharmaceutical intermediate

phytochemical

reference standards from Chinese medicinal herbs (TCM).

standardized herbal extract

Plant extract

Plant Oils, Toxins, Phenolic Acids & Derivatives

The group of Danshen