(±)-Shikonin

SKU: orb1304876

Description

(Rac)-Shikonin (Anchusin) is a bioactive naphthoquinone with documented antimicrobial, anti-tumor, and anti-inflammatory properties. It is utilized in pharmaceutical, cosmetic, and food product development. Research demonstrates its in vitro efficacy in suppressing viability, adhesion, invasion, and migration of cancer cells like MGC-803 via TLR2/NF-κB pathways.

Key Properties

• CAS Number: 54952-43-1
• MW: 288.3
• Purity: 99.73% (May vary between batches)
• Formula: C₁₆H₁₆O₅
• SMILES: O=C1C=2C(C(=O)C=C1C(CC=C(C)C)O)=C(O)C=CC2O
• Target: Others
• Solubility: H2O:< 1 mg/mL (insoluble or slightly soluble);DMSO:10 mM

Bioactivity

• In Vitro:
  At nanomolar concentrations, shikonin inhibits monocyte chemotaxis and calcium flux in response to a variety of CC chemokines (CCL2 [monocyte chemoattractant protein 1], CCL3 [macrophage inflammatory protein 1α], and CCL5 [regulated upon activation, normal T-cell expressed and secreted protein]), the CXC chemokine (CXCL12 [stromal cell-derived factor 1α]), and classic chemoattractants (formylmethionyl-leucine-phenylalanine and complement fraction C5a). Shikonin down-regulates surface expression of CCR5, a primary HIV-1 coreceptor, on macrophages. The anti-HIV and anti-inflammatory activities of shikonin may be related to its interference with chemokine receptor expression and function. Shikonin inhibits enterocyte calcium-activated chloride channels, the inhibitory effect is partially through inhibition of basolateral K+ channel activity.
• Cell Research:
  Freshly isolated human monocytes are plated in a 96-microwell plate (Costar) at 105 cells per well with shikonin at a final concentration of 10, 1, 0.1, 0.01 μM. The numbers of viable cells, as detected by MTS test and the trypan blue exclusion assay, were measured 12 and 24 h after incubation at 37°C in humidified air with 5% CO2. (Only for Reference)

Storage & Handling

• Storage: Powder: -20°C for 3 years | In solvent: -80°C for 1 year | Shipping with blue ice/Shipping at ambient temperature.
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

Anchusa acid, Anchusin, (±)-Shikonin, (Rac)Shikonin, (Rac)-Shikonin, (Rac) Shikonin, Alkanet extract, Inhibitor, inhibit, Shikalkin, Shikonin

Compound Identifiers

PubChem CID

149437686