Dihydrotanshinone I

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Dihydrotanshinone I[1]
Image
2D Structure
Image
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-dihydrophenanthro[1,2-b]furan-10,11-dione
Other names
15,16-dihydrotanshinone I, phenanthro[1,2-b]furan-10,11-dione, 1,2-dihydro-1,6-dimethyl-
Identifiers
3D model (JSmol)
Abbreviations DI
ChemSpider
ECHA InfoCard 100.222.905 Edit this at Wikidata
UNII
  • 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/s1
    Key: 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
  • O=C2c3c(C=1OCC(C=1C2=O)C)ccc4c(cccc34)C
Properties
C18H14O3
Molar mass 278.307 g·mol−1
Appearance Red powder
Density 1.32 g/cm3
Boiling point 479.2 °C (894.6 °F; 752.3 K)
12.9 mg/L (est.)
Solubility in ethanol 1 mg/mL, clear orange to red
log P log Kow = 3.93 (est)
Vapor pressure 3.41x10−9 mmHg
Hazards
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H302, H400
P264, P270, P273, P301+P312, P330, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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[2] and has been reported to have cytotoxicity to a variety of tumor cells,[3] as well as antiviral effects in vitro.[4] Since they were first discovered, over 40 related compounds and over 50 hydrophilic compounds have been isolated from Dan Shen.[2]

References

  1. ^ "Dihydrotanshinone I". PubChem. PubChem. Retrieved 31 August 2015.
  2. ^ a b "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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