Shionone

Names

[ Name ]:
Shionone

[Synonym ]:
(1R,4aS,4bS,6aS,8R,10aR,10bS,12aS)-1,4b,6a,8,10a,12a-Hexamethyl-8-(4-methylpent-3-en-1-yl)hexadecahydrochrysen-2(1H)-one
SHIONONE
21-Shionen-3-one
(1R,4aS,4bS,6aS,8R,10aR,10bS,12aS)-1,4b,6a,8,10a,12a-Hexamethyl-8-(4-methyl-3-penten-1-yl)hexadecahydro-2(1H)-chrysenone
2(1H)-Chrysenone, hexadecahydro-1,4b,6a,8,10a,12a-hexamethyl-8-(4-methyl-3-penten-1-yl)-, (1R,4aS,4bS,6aS,8R,10aR,10bS,12aS)-
3b,5a,8,17ab-Tetramethyl-3-(4-methyl-3-pentenyl)-D-homoandrostan-17-one
18,19-Seco-D:A-friedolup-19-en-3-one
D:A-Friedo-18,19-secolup-19-en-3-one

Biological Activity

[Description]:

Shionone is the major triterpenoid isolated from Aster tataricus, has anti-tussive, anti-inflammatory activities[1][2]. Shionone possesses a unique six-membered tetracyclic skeleton and 3-oxo-4-monomethyl structure[1].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

[In Vivo]

Shionone (orally administration; 80 mg/kg; 3 days; once daily) shows the trend of enhancing sputum secreting, but has no effect on ammonia-induced cough and reduces xylene-induced ear edema[1]. Animal Model: ICR male mice[1] Dosage: 80 mg/kg Administration: Orally administration; 3 days; once daily Result: Reduced the ear edema for 11.3% by use shionone.

[References]

[1]. Sawai S, et al. Molecular characterization of an oxidosqualene cyclase that yields shionone, a unique tetracyclic triterpene ketone of Aster tataricus.FEBS Lett. 2011 Apr 6;585(7):1031-6.

[2]. Yu P, et al. Expectorant, antitussive, anti-inflammatory activities and compositional analysis of Aster tataricus.J Ethnopharmacol. 2015 Apr 22;164:328-33.

Chemical & Physical Properties

[ Density]:
0.9±0.1 g/cm3

[ Boiling Point ]:
485.6±14.0 °C at 760 mmHg

[ Melting Point ]:
161-162°

[ Molecular Formula ]:
C₃₀H₅₀O

[ Molecular Weight ]:
426.717

[ Flash Point ]:
200.5±15.1 °C

[ Exact Mass ]:
426.386169

[ PSA ]:
17.07000

[ LogP ]:
11.00

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.498

Safety Information

[ Safety Phrases ]:
24/25

[ HS Code ]:
29143990