77769-21-2

Basic information

• Product Name: 1,2-dihydrotanshinquinone
• Synonyms: 1,2-dihydrotanshinquinone;8,9-Dihydro-1,6-dimethylphenanthro[1,2-b]furan-10,11-dione;Dihydrotanshiquinone;1,2-Dihydrotanshinone I;1,2-Di-hydrotanshinguinone
• CAS NO: 77769-21-2
• Molecular Formula: C18H14O3
• Molecular Weight: 278.302
• Mol File: 77769-21-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 495.6 °C at 760 mmHg
• Flash Point: 244.6 °C
• Appearance: /
• Density: 1.286 g/cm³
• Vapor Pressure: 5.81E-10mmHg at 25°C
• Refractive Index: 1.629
• CAS DataBase Reference: 1,2-dihydrotanshinquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-dihydrotanshinquinone(77769-21-2)
• EPA Substance Registry System: 1,2-dihydrotanshinquinone(77769-21-2)

Safety Data

• Hazardous Substances Data: 77769-21-2(Hazardous Substances Data)

Usage

Cytotoxicity

IC50 (μg/mL): 5.6 (MIAPaCa-2) (Fronza etal. 2011)

InChI:InChI=1/C18H14O3/c1-9-4-3-5-12-11(9)6-7-13-15(12)17(20)16(19)14-10(2)8-21-18(13)14/h4,6-8H,3,5H2,1-2H3

Upstream product

• 96839-29-1 6-hydroxy-1,6-dimethyl-6,7,8,9-tetrahydrophenanthro[1,2-b]furan-10,11-dione 
• 113297-21-5 4,5-dihydro-3-methylbenzo[1,2-b]furan-4,5-dione 
• 7182-21-0 5-hydroxy-3-methylbenzo<1.2-b>furan 
• 124292-44-0 1-methyl-2-vinylcyclohex-2-en-1-ol 
• 140709-89-3 2-vinylcyclohex-2-en-1-one 
• 33948-36-6 2-iodocyclohex-2-en-1-one 
• 930-68-7 cyclohexenone 

Downstream Products

• 96894-91-6 (+)-(3R,4S)-tanshindiol B 
• 97465-70-8 tanshindiol B 
• 96839-30-4 (+)-(3S,4S)-tanshindiol C 
• 96839-30-4 tanshindiol C 

Relevant articles and documents

Total synthesis of (±)-tanshinol B, tanshinone I, and (±)-tanshindiol B and C

A concise and efficient approach was established for the divergent total synthesis of (±)-tanshindiol B and C and tanshinone I from a ubiquitous ene intermediate in 1-2 steps. This critical intermediate was derived from (±)-tanshinol B, which was synthesized in 50% overall yield over 3 steps using an ultrasound-promoted cycloaddition as a key step. Compared to a previously reported strategy, our approach is more step-economic, thus greatly improving the synthetic efficiency. The bioactivity evaluation indicates that the diol stereochemistry of the tanshidiols has an impact on the EZH2 inhibitory activity.