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S7576

Sigma-Aldrich

Shikonin

≥98% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C16H16O5
Numéro CAS:
54952-43-1
Poids moléculaire :
288.30
Numéro MDL:
MFCD00016668
Code UNSPSC :
12352200
ID de substance PubChem :
329824586
Nomenclature NACRES :
NA.25

Niveau de qualité

200

Pureté

≥98% (HPLC)

Forme

powder or solid

Couleur

red to brown

Solubilité

methanol: 1 mg/mL

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

NEZONWMXZKDMKF-UHFFFAOYSA-N

Catégories apparentées

Description générale

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

Actions biochimiques/physiologiques

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.

Pictogrammes

Exclamation markEnvironment
GHS07,GHS09

Mention d'avertissement

Warning

Mentions de danger

H302,H400

Conseils de prudence

P273 - P301 + P312 + P330

Classification des risques

Acute Tox. 4 Oral - Aquatic Acute 1

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Les clients ont également consulté

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Shikonin A naphthoquinone found in the Chinese herb Shiunko.

Sigma-Aldrich

565850

Shikonin

Ebselen cysteine modifier

Sigma-Aldrich

E3520

Ebselen

β-Lapachone ≥98% (TLC)

Sigma-Aldrich

L2037

β-Lapachone

PF-06284674 ≥98% (HPLC)

Sigma-Aldrich

PZ0301

PF-06284674

3PO ≥98% (HPLC)

Sigma-Aldrich

SML1343

3PO

Lapachol phyproof® Reference Substance

PHL89521

Lapachol

Shikonin phyproof® Reference Substance

PHL89791

Shikonin

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.
Chuanjie Guo et al.
Pharmacological research, 149, 104463-104463 (2019-09-26)
Shikonin is the major bioactive component extracted from the roots of Lithospermum erythrorhizon which is also known as "Zicao" in Traditional Chinese Medicine (TCM). Recent studies have shown that shikonin demonstrates various bioactivities related to the treatment of cancer, inflammation
Ching-Hsein Chen et al.
Annals of surgical oncology, 19(9), 3097-3106 (2012-03-27)
Shikonin is the main naphthoquinone compound of the root of Lithospermum erythrorhizon. Our previous study demonstrated that shikonin possesses anticancer activity in human hepatoma cells. However, the anticancer mechanism of shikonin in human glioma cells is unclear at present. In
Jian-Cai Tang et al.
Life sciences, 204, 71-77 (2018-05-09)
Mutant EGFR Non-small cell lung cancer has benefit from gefitinib, but it has limited effect for wild-type EGFR tumors. Shikonin, a natural naphthoquinone isolated from a traditional Chinese medicine, the plant Lithospermum erythrorhizon (zicao), not only can inhibit the tumor
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