Tanshinone IIA

Base Information

• Chemical Name: Tanshinone IIA
• CAS No.: 568-72-9
• Molecular Formula: C19H18O3
• Molecular Weight: 294.35
• Hs Code.: 29321900
• European Community (EC) Number: 692-941-4
• NSC Number: 686519
• UNII: 4GPC9FQG6L
• DSSTox Substance ID: DTXSID60205352
• Nikkaji Number: J12.293I
• Wikidata: Q27187517
• Pharos Ligand ID: PCSV9997Q32D
• Metabolomics Workbench ID: 125216
• ChEMBL ID: CHEMBL187266
• Mol file: 568-72-9.mol

Synonyms:tanshinone;tanshinone I;tanshinone II A;tanshinone II B;tanshinone IIA;tanshinone IIB;TTE-50

Chemical Property of Tanshinone IIA

Chemical Property:

• Appearance/Colour: Cherry crystal
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 205-207 °C
• Refractive Index: 1.603
• Boiling Point: 480.7 °C at 760 mmHg
• Flash Point: 236.4 °C
• PSA: 47.28000
• Density: 1.209 g/cm³
• LogP: 4.24790
• Storage Temp.: 2-8°C
• Solubility.: methanol: soluble5mg/mL, clear, red-orange to red
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 294.125594432
• Heavy Atom Count: 22
• Complexity: 509

Purity/Quality:

Tanshinone IIA 0.3%, ^*data from raw suppliers

Tanshinone IIA ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=COC2=C1C(=O)C(=O)C3=C2C=CC4=C3CCCC4(C)C
• 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. 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.
• 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
• 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. antineoplastic, bone resorption inhibitor, antiproliferative, apoptosis inducer
• 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.

Technology Process of Tanshinone IIA

There total 18 articles about Tanshinone IIA which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

(+/-)-cryptotanshinone (17545-07-2,35825-57-1,4733-35-1) → tanshinone-IIA (568-72-9)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene; at 20 ℃;

DOI:10.1016/S0040-4039(03)00191-6

Reference yield: 91.0%

Cryptotanshinone (35825-57-1,4733-35-1) → tanshinone-IIA (568-72-9)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene; at 25 ℃; for 42h;

DOI:10.1021/jo00131a006

Reference yield: 40.0%

methyl 2-(1-(methoxycarbonyl)-5,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-4-methylfuran-3-carboxylate → tanshinone-IIA (568-72-9)

Guidance literature:

With sodium; In tetrahydrofuran; at 50 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tetlet.2020.152102

upstream raw materials:

6,6-dimethyl-1-vinylcyclohex-1-ene

4,5-dihydro-3-methylbenzo[1,2-b]furan-4,5-dione

Cryptotanshinone

(+/-)-cryptotanshinone

Downstream raw materials:

neosalvianen

C₄₆H₄₂O₇S

C₄₅H₃₉ClO₆

C₄₅H₃₉ClO₆

Refernces

• 1、 Chang, Junbiao,Duan, Yongtao,Hou, Guodong,Huang, He,Qin, Jinling,Song, Chuanjun,Yao, Yongfang,Zhang, Yixin,Zhao, Cui. "Design, synthesis and biological evaluation of tanshinone IIA-based analogues: Potent inhibitors of microtubule formation and angiogenesis". . . Retrieved 2021/08/03.
• 2、 Jiang, Ying-Yan,Li, Qian,Lu, Wei,Cai, Jun-Chao. "Facile and efficient total synthesis of (±)-cryptotanshinone and tanshinone IIA". . p. 2073 - 2075. Retrieved 2007/10/03.