Shikonin

SIGMA/S7576 - ≥98% (HPLC)

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

CAS Number: 54952-43-1
Empirical Formula (Hill Notation): C₁₆H₁₆O₅
Molecular Weight: 288.30
MDL Number: MFCD00016668
Linear Formula: C₁₆H₁₆O₅
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-S7576-10MG	10 mg	$486.00 1/EA	Add To Favorites
45-S7576-50MG	50 mg	$1670.00 1/EA	Add To Favorites

This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: S7576-10MG.

Properties
Descriptions
Safety Info.
Basic Data

application(s)	metabolomics vitamins, nutraceuticals, and natural products
assay	≥98% (HPLC)
color	red to brown
form	powder or solid
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
Quality Level	200
SMILES string	CC(C)=CCC(O)C1=CC(=O)c2c(O)ccc(O)c2C1=O
solubility	methanol: 1 mg/mL
storage temp.	2-8°C

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:	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).
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).
Biochem/physiol Actions:	Shikonin is a potent anti-fungal agent against C. albicans biofilms. It displays anti-oxidant and chemotherapeutic properties on human glioma cells.
General description:	Shikonin is a major phytochemical compound extracted from the roots of Lithospermum erythrorhizon. It is a natural anthraquinone derivative.
Packaging:	10 mg in glass bottle
Packaging:	50 mg in poly bottle

Symbol	GHS07,GHS09
Signal word	Warning
Hazard statements	H302 - H400
Precautionary statements	P273 - P301 + P312 + P330
Hazard Codes	Xn,N
Risk Statements	22-50/53
Safety Statements	61
RIDADR	UN 3077 9 / PGIII
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

Purity	≥98% (HPLC)
Storage Temp.	2-8°C
UNSPSC	12352200

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