Deoxyshikonin

Modify Date: 2025-08-24 21:15:48

Deoxyshikonin Structure
Deoxyshikonin structure
Common Name Deoxyshikonin
CAS Number 43043-74-9 Molecular Weight 272.296
Density 1.3±0.1 g/cm3 Boiling Point 503.7±50.0 °C at 760 mmHg
Molecular Formula C16H16O4 Melting Point 91ºC
MSDS N/A Flash Point 272.5±26.6 °C

 Use of Deoxyshikonin


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].

 Names

Name 5,8-dihydroxy-2-(4-methylpent-3-enyl)naphthalene-1,4-dione
Synonym More Synonyms

 Deoxyshikonin 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
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
InChIKey VOMDIEGPEURZJO-UHFFFAOYSA-N
SMILES CC(C)=CCCC1=CC(=O)c2c(O)ccc(O)c2C1=O
Storage condition 2-8C

 Safety Information

Safety Phrases 22-24/25
HS Code 2914690090

 Precursor & DownStream

Precursor  0

DownStream  1

 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%

 DeoxyshikoninBioassay

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Name: Cell-based high throughput primary assay to identify activators of GPR151
Source: The Scripps Research Institute Molecular Screening Center
Target: RecName: Full=G-protein coupled receptor 151; AltName: Full=G-protein coupled receptor PGR7; AltName: Full=GPCR-2037; AltName: Full=Galanin receptor 4; AltName: Full=Galanin-receptor-like protein; Short=GalRL
External Id: GPR151_PHUNTER_AG_LUMI_1536_1X%ACT
Name: AlphaScreen-based biochemical high throughput primary assay to identify activators of...
Source: The Scripps Research Institute Molecular Screening Center
Target: N/A
External Id: FBW7_ACT_ALPHA_1536_1X%ACT PRUN
Name: AlphaScreen-based biochemical high throughput primary assay to identify inhibitors of...
Source: The Scripps Research Institute Molecular Screening Center
External Id: MITF_INH_Alpha_1536_1X%INH PRUN
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 Synonyms

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
5,8-Dihydroxy-2-(4-methyl-pent-3-enyl)-1,4-naphthoquinone
5,8-Dihydroxy-2-(4-methyl-3-pentenyl)naphthoquinone
deoxyshikonin
5,8-Dihydroxy-2-(4-methylpent-3-en-1-yl)-1,4-naphthoquinone
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