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568-72-9

Basic Information
CAS No.: 568-72-9
Name: Tanshinone IIA
Article Data: 9
Molecular Structure:
Molecular Structure of 568-72-9 (Tanshinone IIA)
Formula: C19H18O3
Molecular Weight: 294.35
Synonyms: Phenanthro[1,2-b]furan-10,11-dione,6,7,8,9-tetrahydro-1,6,6-trimethyl-;TanshinoneIIA (7CI);1,6,6-Trimethyl-6,7,8,9-tetrahydrophenanthro[1,2-b]furan-10,11-dione;Dan Shenketone;NSC 686518;NSC 686519;Tanshinone B;Tanshinone II;
Density: 1.209 g/cm3
Melting Point: 205-207 °C
Boiling Point: 480.7 °C at 760 mmHg
Flash Point: 236.4 °C
Solubility: Soluble in Alcohol and DMSO
Appearance: Cherry crystal
Safety: 24/25
PSA: 47.28000
LogP: 4.24790
Synthetic route
17545-07-2, 35825-57-1

(+/-)-cryptotanshinone

568-72-9

tanshinone IIA

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene at 20℃;95%
35825-57-1

Cryptotanshinone

568-72-9

tanshinone IIA

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene at 25℃; for 42h;91%

C25H22O4

568-72-9

tanshinone IIA

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In tetrahydrofuran40%

methyl 2-(1-methoxycarbonyl-5,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-4-methylfuran-3- carboxylate

568-72-9

tanshinone IIA

Conditions
ConditionsYield
With sodium In tetrahydrofuran at 50℃; for 1h; Inert atmosphere;40%
18238-29-4

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

113297-21-5

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

A

568-72-9

tanshinone IIA

B

118950-00-8

3,8,8-Trimethyl-8,9,10,11-tetrahydro-phenanthro[4,3-b]furan-4,5-dione

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone 1) neat, ultrasound, 45 deg C, 2h, (or benzene, 12h, reflux), 2) benzene, 12h, reflux; Yield given. Multistep reaction. Yields of byproduct given;
Yield given. Multistep reaction. Yields of byproduct given;
With 2,3-dicyano-5,6-dichloro-p-benzoquinone 1) benzene, reflux, 12h, (or ultrasonification, 45 deg C, 2h), 2) benzene, 12h, reflux; Yield given. Multistep reaction. Yields of byproduct given;
2270-59-9

1-bromo-4-methylpent-3-ene

568-72-9

tanshinone IIA

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 1.) n-BuLi, TMEDA / 1.) hexane, 45 deg C, 30 min, 2.) THF, 55-60 deg C, 20 h
2: 97 percent / AlCl3 / CH2Cl2 / 0.25 h / 0 °C
3: 95 percent / BBr3 / CH2Cl2 / 4 h / -78 - 25 °C
4: 87 percent / DMAP / pyridine / 1.) 0 deg C -> 25 deg C, 1 h, 2.) 25 deg C, 48 h
5: 71 percent / LiCl, 4A sieves, Me4Sn, 2,6-di-tert-butylhydroxytoluene / PdCl2(dppf) / dimethylformamide / 12 h / 90 °C / 2585.7 Torr
6: 1.) LiHMDS, 2,2,2-trifluoroethyl trifluoroacetate, 2.) MsN3, Et3N / 1.) THF, -78 deg C, 45 min, 2.) MeCN, H2O, 25 deg C, 6 h
7: 64 percent / benzene / 24 h / Ambient temperature; Irradiation
8: 84 percent / n-Bu4NF, O2 / tetrahydrofuran / 40 h / 25 °C
9: 100 percent / conc. H2SO4 / ethanol / 0.75 h / 25 °C
10: 91 percent / DDQ / benzene / 42 h / 25 °C
View Scheme
578-57-4

2-bromoanisole

BBr3

BBr3

568-72-9

tanshinone IIA

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 93 percent / PdCl2(dppf) / tetrahydrofuran / 15 h / Heating
2: 97 percent / AlCl3 / CH2Cl2 / 0.25 h / 0 °C
3: 95 percent / BBr3 / CH2Cl2 / 4 h / -78 - 25 °C
4: 87 percent / DMAP / pyridine / 1.) 0 deg C -> 25 deg C, 1 h, 2.) 25 deg C, 48 h
5: 71 percent / LiCl, 4A sieves, Me4Sn, 2,6-di-tert-butylhydroxytoluene / PdCl2(dppf) / dimethylformamide / 12 h / 90 °C / 2585.7 Torr
6: 1.) LiHMDS, 2,2,2-trifluoroethyl trifluoroacetate, 2.) MsN3, Et3N / 1.) THF, -78 deg C, 45 min, 2.) MeCN, H2O, 25 deg C, 6 h
7: 64 percent / benzene / 24 h / Ambient temperature; Irradiation
8: 84 percent / n-Bu4NF, O2 / tetrahydrofuran / 40 h / 25 °C
9: 100 percent / conc. H2SO4 / ethanol / 0.75 h / 25 °C
10: 91 percent / DDQ / benzene / 42 h / 25 °C
View Scheme
171979-69-4

5,5-dimethyl-5,6,7,8-tetrahydronaphthalen-1-ol

568-72-9

tanshinone IIA

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 87 percent / DMAP / pyridine / 1.) 0 deg C -> 25 deg C, 1 h, 2.) 25 deg C, 48 h
2: 71 percent / LiCl, 4A sieves, Me4Sn, 2,6-di-tert-butylhydroxytoluene / PdCl2(dppf) / dimethylformamide / 12 h / 90 °C / 2585.7 Torr
3: 1.) LiHMDS, 2,2,2-trifluoroethyl trifluoroacetate, 2.) MsN3, Et3N / 1.) THF, -78 deg C, 45 min, 2.) MeCN, H2O, 25 deg C, 6 h
4: 64 percent / benzene / 24 h / Ambient temperature; Irradiation
5: 84 percent / n-Bu4NF, O2 / tetrahydrofuran / 40 h / 25 °C
6: 100 percent / conc. H2SO4 / ethanol / 0.75 h / 25 °C
7: 91 percent / DDQ / benzene / 42 h / 25 °C
View Scheme
33214-70-9

1,1-dimethyl-5-methoxytetralin

568-72-9

tanshinone IIA

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 95 percent / BBr3 / CH2Cl2 / 4 h / -78 - 25 °C
2: 87 percent / DMAP / pyridine / 1.) 0 deg C -> 25 deg C, 1 h, 2.) 25 deg C, 48 h
3: 71 percent / LiCl, 4A sieves, Me4Sn, 2,6-di-tert-butylhydroxytoluene / PdCl2(dppf) / dimethylformamide / 12 h / 90 °C / 2585.7 Torr
4: 1.) LiHMDS, 2,2,2-trifluoroethyl trifluoroacetate, 2.) MsN3, Et3N / 1.) THF, -78 deg C, 45 min, 2.) MeCN, H2O, 25 deg C, 6 h
5: 64 percent / benzene / 24 h / Ambient temperature; Irradiation
6: 84 percent / n-Bu4NF, O2 / tetrahydrofuran / 40 h / 25 °C
7: 100 percent / conc. H2SO4 / ethanol / 0.75 h / 25 °C
8: 91 percent / DDQ / benzene / 42 h / 25 °C
View Scheme
100-66-3

methoxybenzene

2-chloro-decalin

2-chloro-decalin

568-72-9

tanshinone IIA

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 1.) n-BuLi, TMEDA / 1.) hexane, 45 deg C, 30 min, 2.) THF, 55-60 deg C, 20 h
2: 97 percent / AlCl3 / CH2Cl2 / 0.25 h / 0 °C
3: 95 percent / BBr3 / CH2Cl2 / 4 h / -78 - 25 °C
4: 87 percent / DMAP / pyridine / 1.) 0 deg C -> 25 deg C, 1 h, 2.) 25 deg C, 48 h
5: 71 percent / LiCl, 4A sieves, Me4Sn, 2,6-di-tert-butylhydroxytoluene / PdCl2(dppf) / dimethylformamide / 12 h / 90 °C / 2585.7 Torr
6: 1.) LiHMDS, 2,2,2-trifluoroethyl trifluoroacetate, 2.) MsN3, Et3N / 1.) THF, -78 deg C, 45 min, 2.) MeCN, H2O, 25 deg C, 6 h
7: 64 percent / benzene / 24 h / Ambient temperature; Irradiation
8: 84 percent / n-Bu4NF, O2 / tetrahydrofuran / 40 h / 25 °C
9: 100 percent / conc. H2SO4 / ethanol / 0.75 h / 25 °C
10: 91 percent / DDQ / benzene / 42 h / 25 °C
View Scheme
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Chemistry

Molecular Formula: C14H10O3
Molar mass: 226.23 g/mol
Density: 1.209 g/cm3
Flash Point: 236.4 °C
Index of Refraction: 1.587
Boiling Point: 480.7 °C at 760 mmHg
Vapour Pressure: 2.12E-09 mmHg at 25 °C
Product categories of Tanshinone IIA (CAS NO.568-72-9): Plant Oils, Toxins, Phenolic Acids & Derivatives;Danshen
Structure of Tanshinone IIA (CAS NO.568-72-9):
        
XLogP3-AA: 4.3
H-Bond Donor: 0
H-Bond Acceptor: 3
IUPAC Name of Tanshinone IIA (CAS NO.568-72-9): 1,6,6-Trimethyl-8,9-dihydro-7H-naphtho[1,2-g][1]benzofuran-10,11-dione
Canonical SMILES: CC1=COC2=C1C(=O)C(=O)C3=C2C=CC4=C3CCCC4(C)C
InChI: 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 
InChIKey: HYXITZLLTYIPOF-UHFFFAOYSA-N

Specification

 Tanshinone IIA , its cas register number is 568-72-9. It also can be called Phenanthro[1,2-b]furan-10,11-dione, 6,7,8,9-tetrahydro-1,6,6-trimethyl- and 1,6,6-Trimethyl-6,7,8,9-tetrahydrophenanthro[1,2-b]furan-10,11-dione .