568-73-0

Basic information

• Product Name: Tanshinone I
• Synonyms: 1,6-dimethyl-phenanthro[1,2-b]furan-10,11-dione;1,6,6-TRIMETHYL-6,7,8,9-TETRAHYDRO-PHENANTHRO[1,2-B]FURAN-10,11-DIONE;3,8,8-TRIMETHYL-8,9,10,11-TETRAHYDROPHENANTHRO[1,2-B]FURAN-1,2-DIONE;AKOS NCG1-0066;TANSHINONE I;TANSHINONES IIA;TANSHINON I;Tanshinone
• CAS NO: 568-73-0
• Molecular Formula: C₁₈H₁₂O₃
• Molecular Weight: 294.34
• Product Categories: Anthraquinones, Hydroquinones and Quinones;Natural Plant Extract;The group of Danshen;Herb extract;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 568-73-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 233-234°C
• Boiling Point: 498 °C at 760 mmHg
• Flash Point: 245.9 °C
• Appearance: red/
• Density: 1.324 g/cm³
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble1mg/mL
• CAS DataBase Reference: Tanshinone I(CAS DataBase Reference)
• NIST Chemistry Reference: Tanshinone I(568-73-0)
• EPA Substance Registry System: Tanshinone I(568-73-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 568-73-0(Hazardous Substances Data)

Usage

Chemical Properties

Purple to Brown powder

Uses

Tanshinone I is an extract from Danshen (Radix Salvia miltiorrhizae) and has been used for the treatment of cerebrovascular diseases such as ischemic stroke.

Cytotoxicity

IC50 (μg/mL): 2.96 (A549), 2.14 (TOV-21G) (Chang et al. 2013)IC50 (μg/mL): 10.5 (MIAPaCa-2) (Fronzaet al. 2011)

InChI:InChI=1/C18H12O3/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/h3-8H,1-2H3

Upstream product

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Relevant articles and documents

A facile three-step total synthesis of tanshinone I

A facile synthetic approach for total synthesis of tanshinone I has been accomplished. The key precursor is a novel compound, epoxy phenanthraquinone. And this synthesis of tanshinone I is achieved in only three simple stages, which include Diels–Alder reaction, Δ2-Weitz–Scheffer-type epoxidation, and Feist–Bénary reaction from commercially available styrene.

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.

Facile construction of 3-hydroxyphenanthrene-1,4-diones: Key intermediates to tanshinone i and its A-ring-modified analogue

A mild synthetic approach was established allowing for a convenient construction of tricyclic hydroxyphenanthraquinones, the key precursor for total synthesis of tanshinone I. This tandem process includes decarboxylative radical alkylation, intramolecular C-H arylation and one-pot O-demethylation and aromatization. Variously substituted phenylpropanoic acids were well tolerated in this approach, and synthesis of tanshinone I (1) was finally successful in six straight steps in 19% overall yields from commercially available 5-bromovanillin.