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picrocrocin

Names

[ CAS No. ]:
138-55-6

[ Name ]:
picrocrocin

[Synonym ]:
saffron-bitter
Picrocrocine
(4R)-2,6,6-trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexene-1-carbaldehyde

Biological Activity

[Description]:

Picrocrocin, an apocarotenoid found in the flowers of Cochliobolus sativus. Picrocrocin shows anticancer effect. Picrocrocin exhibits growth inhibitory effects against SKMEL-2 human malignant melanoma cells[1].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cancer

[In Vitro]

Picrocrocin exerted growth inhibitory effects on the SK-MEL-2 melanoma cells. The IC50 of picrocrocin against the SK-MEL-2 cells was 20 μM at 24-h incubation. The antiproliferative activity of picrocrocin was due to apoptosis and cell cycle arrest. In addition, picrocrocin enhanced the ROS levels and decreased the MMP levels of SK-MEL-2 cells. Finally, picrocrocin inhibited the JAK/STAT5 signalling pathway in the SK-MEL-2 melanoma cells[1].

[References]

[1]. Yu L, et al. Picrocrocin exhibits growth inhibitory effects against SKMEL- 2 human malignant melanoma cells by targeting JAK/ STAT5 signaling pathway, cell cycle arrest and mitochondrial mediated apoptosis. J BUON. 2018 Jul-Aug;23(4):1163-1168.

Chemical & Physical Properties

[ Density]:
1.31g/cm3

[ Boiling Point ]:
520.4ºC at 760mmHg

[ Melting Point ]:
196 ºC (ethyl acetate )

[ Molecular Formula ]:
C16H26O7

[ Molecular Weight ]:
330.37300

[ Flash Point ]:
187.1ºC

[ Exact Mass ]:
330.16800

[ PSA ]:
116.45000

[ Vapour Pressure ]:
5.27E-13mmHg at 25°C

[ Index of Refraction ]:
1.561

[ Water Solubility ]:
Sparingly soluble (24 g/L) (25 ºC)

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds