Dihydrotanshinone I

Dihydrotanshinone I^[1]
	2D Structure 2D Structure
	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-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
CAS Number	87205-99-0;
3D model (JSmol)	Interactive image;
Abbreviations	DI
ChemSpider	9600799;
ECHA InfoCard	100.222.905
PubChem CID	11425923;
UNII	562G9360V6;
CompTox Dashboard (EPA)	DTXSID20236187 ;
	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/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;
	SMILES O=C2c3c(C=1OCC(C=1C2=O)C)ccc4c(cccc34)C;
Properties
Chemical formula	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)
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	3.41×10−9 mmHg
Hazards
	GHS labelling:
Pictograms
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 [77 °F], 100 kPa). Infobox references

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] In a study Dihydrotanshinone I inhibited the 17,20-lyase activity of CYP17A1 while having minor impact on 17α-hydroxylase and CYP21A2 activities ^[5]. Since they were first discovered, over 40 related compounds and over 50 hydrophilic compounds have been isolated from Dan Shen.^[2]

References

↑ "Dihydrotanshinone I". PubChem. Retrieved 31 August 2015.
1 2 "HSDB: DIHYDROTANSHINONE I". NIH. Retrieved 1 September 2015.
↑ 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.
↑ 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.
↑ Li, Kaige; Yakubu, Jibira; Jørgensen, Flemming Steen; Pandey, Amit V. (2026-01-14). "Dihydrotanshinone as a Natural Product-Based CYP17A1 Lyase Inhibitor for Hyperandrogenic Disorders". Biomolecules. 16 (1): 144. doi:10.3390/biom16010144. ISSN 2218-273X. PMC 12838644. PMID 41594684.

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[PC-1] "Dihydrotanshinone I". PubChem. Retrieved 31 August 2015.

[NIH-2] 1 2 "HSDB: DIHYDROTANSHINONE I". NIH. Retrieved 1 September 2015.

[ABBS-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.

[pmid34198325-4] 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.

[5] Li, Kaige; Yakubu, Jibira; Jørgensen, Flemming Steen; Pandey, Amit V. (2026-01-14). "Dihydrotanshinone as a Natural Product-Based CYP17A1 Lyase Inhibitor for Hyperandrogenic Disorders". Biomolecules. 16 (1): 144. doi:10.3390/biom16010144. ISSN 2218-273X. PMC 12838644. PMID 41594684.

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References