Beta-hydroxyisovalerylshikonin is a naturally occurring compound extracted from Lithospermum erythrorhizon. It is a potent PTK inhibitor (antagonist) with IC50 of 0.7 μM and 1 μM for EGFR and v-Src receptors, respectively. Beta-hydroxyisovalerylshikonin has inhibitory activities on a variety of tumor cell lines and can efficiently induce the death of NCI-H522 and DMS114 cells.

Physicochemical Properties

Molecular Formula	C21H24O7
Molecular Weight	388.4111
Exact Mass	388.152
CAS #	7415-78-3
PubChem CID	479502
Appearance	Brown to black solid powder
Density	1.312g/cm3
Boiling Point	616.9ºC at 760 mmHg
Flash Point	215.8ºC
Index of Refraction	1.596
LogP	2.832
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	7
Heavy Atom Count	28
Complexity	700
Defined Atom Stereocenter Count	1
SMILES	CC(=CC[C@H](C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)OC(=O)CC(C)(C)O)C
InChi Key	MXANJRGHSFELEJ-MRXNPFEDSA-N
InChi Code	InChI=1S/C21H24O7/c1-11(2)5-8-16(28-17(25)10-21(3,4)27)12-9-15(24)18-13(22)6-7-14(23)19(18)20(12)26/h5-7,9,16,22-23,27H,8,10H2,1-4H3/t16-/m1/s1
Chemical Name	[(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-hydroxy-3-methylbutanoate
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

References	[1]. Beta-hydroxyisovalerylshikonin is a novel and potent inhibitor of protein tyrosine kinases. Jpn J Cancer Res. 2002 Aug;93(8):944-51.
Additional Infomation	beta-Hydroxyisovalerylshikonin has been reported in Onosma paniculata, Lithospermum erythrorhizon, and Echium plantagineum with data available.

Solubility Data

Solubility (In Vitro)

DMSO : ~10 mg/mL (~25.75 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 1 mg/mL (2.57 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 10.0 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 1 mg/mL (2.57 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 10.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.5746 mL	12.8730 mL	25.7460 mL
	5 mM	0.5149 mL	2.5746 mL	5.1492 mL
	10 mM	0.2575 mL	1.2873 mL	2.5746 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.