Shikonin

Names

[ CAS No. ]:
517-88-4

[ Name ]:
Shikonin

[Synonym ]:
Alkannin (VAN)
5,8-dihydroxy-2-[(1S)-1-hydroxy-4-methylpent-3-en-1-yl]naphthalene-1,4-dione
5,8-Dihydroxy-2-[(1S)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-naphthoquinone
Anchusa acid (VAN)
Anchusin (VAN)
C.I. Natural Red 20
(S)-5,8-Dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthalenedione
1,4-Naphthalenedione, 5,8-dihydroxy-2-[(1S)-1-hydroxy-4-methyl-3-penten-1-yl]-
Alkanna red (VAN)
Alkannin
Anchusa acid
Anchusin
(-)-5,8-Dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone
Alkanna Red
5,8-Dihydroxy-2-[(1S)-1-hydroxy-4-methyl-3-penten-1-yl]-1,4-naphthoquinone
C.I. Natural Red 20 (VAN)
EINECS 208-245-7
(1-Hydroxy-3-isohexenyl)naphthazarine

Biological Activity

[Description]:

Alkannin, found in Alkanna tinctoria, is used as a food coloring. Alkannin shows anticancer activity, arrests cell cycle, and induces apoptosis. Alkannin improves hepatic inflammation in a Rho-kinase pathway[1][2][3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

[In Vitro]

Alkannin inhibits HCT-116 and SW-480 cells growth with IC50s of 2.38 and 4.53 µM, respectively[1].

[References]

[1]. Hosokawa Y, et al. Alkannin inhibits CCL3 and CCL5 production in human periodontal ligament cells. Cell Biol Int. 2016 Dec;40(12):1380-1385.

[2]. Huu Tung N, et al. Naphthoquinone components from Alkanna tinctoria (L.) Tausch show significant antiproliferative effects on human colorectal cancer cells. Phytother Res. 2013 Jan;27(1):66-70.

[3]. Xue W, et al. Alkannin Inhibited Hepatic Inflammation in Diabetic Db/Db Mice. Cell Physiol Biochem. 2018;45(6):2461-2470.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
567.4±50.0 °C at 760 mmHg

[ Melting Point ]:
149°

[ Molecular Formula ]:
C₁₆H₁₆O₅

[ Molecular Weight ]:
288.295

[ Flash Point ]:
311.0±26.6 °C

[ Exact Mass ]:
288.099762

[ PSA ]:
94.83000

[ LogP ]:
4.35

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.642

MSDS

Click to get detail MSDS

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Precursor & DownStream

Precursor

DownStream

Articles

Integrative analysis of 111 reference human epigenomes.

Nature 518(7539) , 317-30, (2015)

The reference human genome sequence set the stage for studies of genetic variation and its association with human disease, but epigenomic studies lack a similar reference. To address this need, the NI...