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Dihydrotanshinone I

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Dihydrotanshinone I
Image
2D Structure
2D Structure
Image
3D Conformer
3D Conformer
Names
IUPAC name 4,17β-Dimethyl-15-oxagona-1,3,5,7,9,13-hexaene-11,12-dione
Systematic IUPAC name (1R)-1,6-Dimethyl-1,2-dihydrophenanthrofuran-10,11-dione
Other names 15,16-dihydrotanshinone I, phenanthrofuran-10,11-dione, 1,2-dihydro-1,6-dimethyl-
Identifiers
CAS Number
3D model (JSmol)
Abbreviations DI
ChemSpider
ECHA InfoCard 100.222.905 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/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/h3-7,10H,8H2,1-2H3/t10-/m0/s1Key: HARGZZNYNSYSGJ-JTQLQIEISA-N
  • 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/h3-7,10H,8H2,1-2H3
SMILES
  • O=C2c3c(C=1OCC(C=1C2=O)C)ccc4c(cccc34)C
Properties
Chemical formula C18H14O3
Molar mass 278.307 g·mol
Appearance Red powder
Density 1.32 g/cm
Boiling point 479.2 °C (894.6 °F; 752.3 K)
Solubility in water 12.9 mg/L (est.)
Solubility in ethanol 1 mg/mL, clear orange to red
log P log Kow = 3.93 (est)
Vapor pressure 3.41x10 mmHg
Hazards
GHS labelling:
Pictograms GHS07: Exclamation markGHS09: Environmental hazard
Signal word Warning
Hazard statements H302, H400
Precautionary statements P264, P270, P273, P301+P312, P330, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Dihydrotanshinone I (DI) is a naturally occurring compound extracted from Salvia miltiorrhiza Bunge, also known as Chinese sage, red sage root, and the Chinese herbal Dan Shen. It belongs to a class of lipophilic abietane diterpenoids and has been reported to have cytotoxicity to a variety of tumor cells, as well as antiviral effects in vitro. Since they were first discovered, over 40 related compounds and over 50 hydrophilic compounds have been isolated from Dan Shen.

References

  1. "Dihydrotanshinone I". PubChem. Retrieved 31 August 2015.
  2. ^ "HSDB: DIHYDROTANSHINONE I". NIH. Retrieved 1 September 2015.
  3. Bian W, Chen F, Bai L, Zhang P, Qin W (January 2008). "Dihydrotanshinone I inhibits angiogenesis both in vitro and in vivo". Acta Biochimica et Biophysica Sinica. 40 (1): 1–6. doi:10.1111/j.1745-7270.2008.00370.x. PMID 18180848.
  4. Lim CT, Tan KW, Wu M, Ulferts R, Armstrong LA, Ozono E, Drury LS, Milligan JC, Zeisner TU, Zeng J, Weissmann F, Canal B, Bineva-Todd G, Howell M, O'Reilly N, Beale R, Kulathu Y, Labib K, Diffley JF (July 2021). "Identifying SARS-CoV-2 antiviral compounds by screening for small molecule inhibitors of Nsp3 papain-like protease". The Biochemical Journal. 478 (13): 2517–2531. doi:10.1042/BCJ20210244. PMC 8286840. PMID 34198325.


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