Deoxyshikonin

Names

[ Name ]:
Deoxyshikonin

[Synonym ]:
1'O-deoxyshikonin
ARNEBIN-7
5,8-Dihydroxy-2-(4-methyl-3-penten-1-yl)-1,4-naphthoquinone
deoxyalkannin
5,8-Dihydroxy-2-(4-methyl-3-pentenyl)-1,4-naphthalenedione
11-Deoxyalkannin
1,4-Naphthalenedione, 5,8-dihydroxy-2-(4-methyl-3-pentenyl)-
5,8-Dihydroxy-2-(4-methyl-pent-3-enyl)-1,4-naphthoquinone
1,4-Naphthalenedione, 5,8-dihydroxy-2-(4-methyl-3-penten-1-yl)-
5,8-Dihydroxy-2-(4-methyl-3-pentenyl)naphthoquinone
deoxyshikonin
5,8-Dihydroxy-2-(4-methylpent-3-en-1-yl)-1,4-naphthoquinone

Biological Activity

[Description]:

Deoxyshikonin is isolated from Lithospermum erythrorhizon Sieb with antitumor activity. Deoxyshikonin increases the expression of VEGF-C and VEGF-A mRNA in HMVEC-dLy, promotes HIF-1α and HIF-1β subunit interaction and binds to specific DNA sequences targeted by HIF, indicates a prolymphangiogenesis as well as a proangiogenesis effect in vitro[1]. Deoxyshikonin shows significant synergic antimicrobial activity with tetracycline against S. pneumonia (MIC=17 μg/mL), also shows significantly inhibitory activities against MRSA[2].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Cardiovascular Disease

Research Areas >> Infection

Signaling Pathways >> Metabolic Enzyme/Protease >> HIF/HIF Prolyl-Hydroxylase

Signaling Pathways >> Anti-infection >> Bacterial

[References]

[1]. Prangsaengtong O, et al. Enhancement of Lymphangiogenesis In Vitro via the Regulations of HIF-1α Expression and Nuclear Translocation by Deoxyshikonin. Evid Based Complement Alternat Med. 2013;2013:148297.

[2]. Zhang S, et al. Antibacterial effects of Traditional Chinese Medicine monomers against Streptococcus pneumoniae via inhibiting pneumococcal histidine kinase (VicK). Front Microbiol. 2015 May 20;6:479.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
503.7±50.0 °C at 760 mmHg

[ Melting Point ]:
91ºC

[ Molecular Formula ]:
C₁₆H₁₆O₄

[ Molecular Weight ]:
272.296

[ Flash Point ]:
272.5±26.6 °C

[ Exact Mass ]:
272.104858

[ PSA ]:
74.60000

[ LogP ]:
4.72

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.611

[ Storage condition ]:
2-8C

MSDS

Click to get detail MSDS

Safety Information

[ Safety Phrases ]:
22-24/25

[ HS Code ]:
2914690090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914690090

[ Summary ]:
2914690090 other quinones。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%