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S7576

Sigma-Aldrich

Shikonin

≥98% (HPLC)

Synonym(s):

(±)-5,8-Dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone, (±)-Alkannin, (±)-Shikalkin, (±)-Shikonin

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About This Item

Empirical Formula (Hill Notation):
C16H16O5
CAS Number:
54952-43-1
Molecular Weight:
288.30
MDL number:
MFCD00016668
UNSPSC Code:
12352200
PubChem Substance ID:
329824586
NACRES:
NA.25

Assay

≥98% (HPLC)

form

powder or solid

color

red to brown

solubility

methanol: 1 mg/mL

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

C\C(C)=C\CC(O)C1=CC(=O)c2c(O)ccc(O)c2C1=O

InChI

1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3

InChI key

NEZONWMXZKDMKF-UHFFFAOYSA-N

Related Categories

General description

Shikonin is a major phytochemical compound extracted from the roots of Lithospermum erythrorhizon. It is a natural anthraquinone derivative.

Application

Shikonin has been used:
  • to enhance the anti-tumor activity of gefitinib on tyrosine kinase receptor epidermal growth factor receptor (EGFR) in wild-type lung cancer cells
  • as an inhibitor of renal aerobic glycosis and a potential
  • as an anti-inflammatory agent to test its role to improve lipopolysaccharide (LPS)-induced cardiac dysfunction
  • to stimulate bone marrow-derived macrophages (BMDMs) to test the effect of Interferon regulatory factor 1 on cell death

Biochem/physiol Actions

Naphthoquinone isolated from Arnebia sp. Used as an anti-inflammatory treatment in traditional chinese medicine (TCM). Inhibits chemokine receptor function and suppresses HIV-1.† Circumvents cancer drug resistance by induction of cell death through a necroptotic pathway.† Treatment of cancer cells with shikonin suppressed glycolysis via the inhibition of pyruvate kinase M2 (PKM2).
Shikonin is a potent anti-fungal agent against C. albicans biofilms. It displays anti-oxidant and chemotherapeutic properties on human glioma cells.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H400

Precautionary Statements

P273 - P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Hui-Ming Chen et al.
Cancer immunology, immunotherapy : CII, 61(11), 1989-2002 (2012-04-25)
Immunogenic cell death is characterized by damage-associated molecular patterns, which can enhance the maturation and antigen uptake of dendritic cells. Shikonin, an anti-inflammatory and antitumor phytochemical, was exploited here as an adjuvant for dendritic cell-based cancer vaccines via induction of
Jen-Tsung Yang et al.
PloS one, 9(4), e94180-e94180 (2014-04-10)
Shikonin is a quinone-containing natural product that induces the apoptotic death of some cancer cell lines in culture through increasing intracellular reactive oxygen species (ROS). Quinone-based drugs have shown potential in the clinic, making shikonin an interesting compound to study.
Ke Gong et al.
Free radical biology & medicine, 51(12), 2259-2271 (2011-10-21)
Although shikonin, a naphthoquinone derivative, has showed anti-cancer activity, its precise molecular anti-tumor mechanism remains to be elucidated. In this study, we investigated the effects of shikonin on human hepatocellular carcinoma (HCC) in vitro and in vivo. Our results showed
Konstantinos N Kontogiannopoulos et al.
International journal of pharmaceutics, 422(1-2), 381-389 (2011-10-08)
The interest of drug delivery has focused on the creation of new formulations with improved properties, taking much attention to the drug release from the carrier. Liposomes have already been commercialized, while dendrimers and hyperbranched polymers are emerging as potentially
Yongwei Wang et al.
Biochemical pharmacology, 88(3), 322-333 (2014-02-14)
Although gemcitabine is currently the best chemotherapeutic agent available for the treatment of advanced pancreatic cancer, eventual failure of response is a significant clinical problem. Therefore, novel therapeutic approaches against this disease are highly needed. The aim of this study
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