6,6,14-trimethyl-12-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),2(7),8,11(15),13-pentaene-16,17-dione

• ChemBase ID: 72990
• Molecular Formular: C19H18O3
• Molecular Mass: 294.34442
• Monoisotopic Mass: 294.12559444
• SMILES: C1CC(c2c(C1)c1c(cc2)c2c(C(=O)C1=O)c(co2)C)(C)C
• Canonical SMILES: O=C1c2c3CCCC(c3ccc2c2c(C1=O)c(C)co2)(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

NAMES AND DATABASE IDS

Names

• IUPAC name: 6,6,14-trimethyl-12-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),2(7),8,11(15),13-pentaene-16,17-dione; 6,6,14-trimethyl-12-oxatetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1(10),2(7),8,11(15),13-pentaene-16,17-dione
• IUPAC Traditional name: 6,6,14-trimethyl-12-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),2(7),8,11(15),13-pentaene-16,17-dione; 6,6,14-trimethyl-12-oxatetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1(10),2(7),8,11(15),13-pentaene-16,17-dione; tanshinone iia
• Synonyms: Tanshinone B; Tanshinone II; Tanshinone IIA; 1,6,6-Trimethyl-6,7,8,9-tetrahydrophenanthro[1,2-b]furan-10,11-dione; Dan Shen ketone; Tanshinone IIA; 1,6,6-trimethyl-6,7,8,9-tetrahydrophenanthro[1,2-b]furan-10,11-dione

Database IDs

• CAS Number: 568-72-9
• MDL Number: MFCD00238692
• PubChem SID: 162037910
• PubChem CID: 164676

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.5316944
• LogD (pH = 7.4): 4.5316944
• Log P: 4.5316944
• Molar Refractivity: 85.089 cm^3
• Polarizability: 33.140404 Å^3
• Polar Surface Area: 47.28 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: methanol: soluble5 mg/mL, clear, red-orange to red
• Apperance: powder, red; Red powder
• Melting Point: 204-208 °C

Safety Information

• Storage Condition: -20°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97% (HPLC); ≥98.0% (HPLC)
• Grade: analytical standard
• Salt Data: Free Base
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C19H18O3
• Classification: Genuine Natural Compounds

DETAILS

Selleck Chemicals - S2365

Research Area: Cardiovascular Disease , Neurological Disease
Biological Activity:
Tanshinone IIA(Tanshinone B) is the most abundant diterpene quinone in Danshen, Salviae miltiorrhizae Radix, a widely prescribed traditional herbal medicine that is used to treat cardiovascular and inflammatory diseases. Recently, tanshinone IIA was demonstrated to induce cell death and apoptosis in a variety of tumors. [1]

Sigma Aldrich - T4952

Biochem/physiol Actions
Phenanthrenequinone constituent of Chinese medicinal herb Danshen (Salvia miltiorrhiza). Anti-inflammatory. Antioxidant. Cytotoxic against a variety of cell lines, inlcuding human glioma cells.

Sigma Aldrich - 51704

Biochem/physiol Actions
Phenanthrenequinone constituent of Chinese medicinal herb Danshen (Salvia miltiorrhiza). Anti-inflammatory. Antioxidant. Cytotoxic against a variety of cell lines, inlcuding human glioma cells.

REFERENCES

• Su CC, et al. Planta Med. 2008 Sep;74(11):1357-62