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Tanshinone IIA (Dan Shen ketone)

Alias: Tan IIA; Dan Shen ketone
Cat No.:V1986 Purity: ≥98%
Tanshinone IIA (Tan IIA;Dan Shen ketone),derived from phenanthrene-quinone, which is isolated from Salvia miltiorrhiza BUNGE.
Tanshinone IIA (Dan Shen ketone)
Tanshinone IIA (Dan Shen ketone) Chemical Structure CAS No.: 568-72-9
Product category: VEGFR
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
25mg
50mg
100mg
250mg
500mg
Other Sizes

Other Forms of Tanshinone IIA (Dan Shen ketone):

  • Sinomenine (Cucoline)
Official Supplier of:
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Top Publications Citing lnvivochem Products
Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Tanshinone IIA (Tan IIA; Dan Shen ketone), derived from phenanthrene-quinone, which is isolated from Salvia miltiorrhiza BUNGE. In these countries, it is traditionally used in herbal medicine to treat arthritis and rheumatism. Its ability to relieve other types of pain is restricted, though. Sinomenine is a derivative of morphinan that is connected to non-opioid cough suppressants like dextromethorphan and opioids like levorphanol.

Biological Activity I Assay Protocols (From Reference)
Targets
VEGF/VEGFR2
ln Vitro
Tanshinone IIA (Tanshinone B) is the most prevalent diterpene quinone in Danshen, where Salviae miltiorrhizae Radix is a commonly prescribed traditional herbal remedy used to treat inflammatory and cardiovascular conditions. Heart myocytes are shielded from oxidative stress-induced apoptosis by tanshinone IIA. The prevention of lipid peroxidation, enhanced scavenging of oxygen free radicals, and upregulation of the Bcl-2/Bax ratio all contribute to the in vivo protection.[1] It has recently been shown that tanshinone IIA can cause apoptosis and cell death in a range of tumor types.[2]
ln Vivo
LD50: Rats 25g/kg (i.g.) [3]
Animal Protocol
Male ICR mice (25–30 g)[4]
10 or 20 mg/kg
P.o.
References

[1]. Eur J Pharmacol . 2007 Jul 30;568(1-3):213-21.

[2]. Int J Cancer . 2005 Sep 20;116(5):799-807.

[3]. Brain Res Bull . 2012 Sep 1;88(6):581-8.

[3]. 2014,5, 1528-1532

Additional Infomation
1,6,6-trimethyl-8,9-dihydro-7H-naphtho[1,2-g]benzofuran-10,11-dione is an abietane diterpenoid.
Tanshinone IIA has been reported in Salvia miltiorrhiza, Salvia glutinosa, and other organisms with data available.
See also: Salvia Miltiorrhiza Root (part of).
Mechanism of Action
Doxorubicin, one of the original anthracyclines, remains among the most effective anticancer drugs ever developed. Clinical use of doxorubicin is, however, greatly limited by its serious adverse cardiac effects that may ultimately lead to cardiomyopathy and heart failure. Tanshinone IIA is the main effective component of Salvia miltiorrhiza known as 'Danshen' in traditional Chinese medicine for treating cardiovascular disorders. The objective of this study was set to evaluate the protective effect of tanshinone IIA on doxorubicin-induced cardiomyocyte apoptosis, and to explore its intracellular mechanism(s). Primary cultured neonatal rat cardiomyocytes were treated with the vehicle, doxorubicin (1 uM), tanshinone IIA (0.1, 0.3, 1 and 3 uM), or tanshinone IIA plus doxorubicin. /The authors/ found that tanshinone IIA (1 and 3 uM) inhibited doxorubicin-induced reactive oxygen species generation, reduced the quantity of cleaved caspase-3 and cytosol cytochrome c, and increased BcL-x(L) expression, resulting in protecting cardiomyocytes from doxorubicin-induced apoptosis. In addition, Akt phosphorylation was enhanced by tanshinone IIA treatment in cardiomyocytes. The wortmannin (100 nM), LY294002 (10 nM), and siRNA transfection for Akt significantly reduced tanshinone IIA-induced protective effect. These findings suggest that tanshinone IIA protects cardiomyocytes from doxorubicin-induced apoptosis in part through Akt-signaling pathways, which may potentially protect the heart from the severe toxicity of doxorubicin.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C19H18O3
Molecular Weight
294.3444
Exact Mass
294.125
CAS #
568-72-9
Related CAS #
568-72-9
PubChem CID
164676
Appearance
Pink to red solid
Density
1.2±0.1 g/cm3
Boiling Point
480.7±44.0 °C at 760 mmHg
Melting Point
205-207ºC
Flash Point
236.4±21.1 °C
Vapour Pressure
0.0±1.2 mmHg at 25°C
Index of Refraction
1.588
LogP
5.47
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
0
Heavy Atom Count
22
Complexity
509
Defined Atom Stereocenter Count
0
SMILES
O1C([H])=C(C([H])([H])[H])C2C(C(C3=C(C1=2)C([H])=C([H])C1=C3C([H])([H])C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H])=O)=O
InChi Key
HYXITZLLTYIPOF-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H18O3/c1-10-9-22-18-12-6-7-13-11(5-4-8-19(13,2)3)15(12)17(21)16(20)14(10)18/h6-7,9H,4-5,8H2,1-3H3
Chemical Name
1,6,6-trimethyl-8,9-dihydro-7H-naphtho[1,2-g][1]benzofuran-10,11-dione
Synonyms
Tan IIA; Dan Shen ketone
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product is not stable in solution, please use freshly prepared working solution for optimal results.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: > 10 mM
Water: NA
Ethanol: NA
Solubility (In Vivo)
5% DMSO+30% PEG 300+2% Tween 80+ddH2O: 0.2mg/mL (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.3974 mL 16.9872 mL 33.9743 mL
5 mM 0.6795 mL 3.3974 mL 6.7949 mL
10 mM 0.3397 mL 1.6987 mL 3.3974 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Biological Data
  • Inhibition of human MCF-7 breast cancer cell growth by tanshinone IIA. Int J Cancer . 2005 Sep 20;116(5):799-807.
  • Inhibition of human MCF-7 breast cancer cell colony formation by tanshinone IIA. Int J Cancer . 2005 Sep 20;116(5):799-807.
  • Inhibition of tumor growth in nude mice xenografted with human breast IDC by tanshinone IIA. Int J Cancer . 2005 Sep 20;116(5):799-807.
  • Increase of caspase-3 protein expression by tanshinone IIA. Int J Cancer . 2005 Sep 20;116(5):799-807.
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