β,β-Dimethylacrylshikonin (Isoarnebin I) is a naphthoquinone analogue found in Lithospermum vulgare. It induces the expression of eNOS, VEGF and HIF-1α through the PI3K pathway and promotes angiogenesis. β,β-Dimethylacrylshikonin has anti-tumor effects.

Physicochemical Properties

Molecular Formula	C21H22O6
Molecular Weight	370.3958
Exact Mass	370.141
CAS #	24502-79-2
Related CAS #	β,β-Dimethylacrylalkannin;34539-65-6
PubChem CID	479499
Appearance	Brown to reddish brown solid powder
Density	1.3±0.1 g/cm3
Boiling Point	653.2±55.0 °C at 760 mmHg
Melting Point	103ºC
Flash Point	362.8±28.0 °C
Vapour Pressure	0.0±2.1 mmHg at 25°C
Index of Refraction	1.616
LogP	4.45
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	6
Heavy Atom Count	27
Complexity	706
Defined Atom Stereocenter Count	1
SMILES	CC(=CC[C@H](C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)OC(=O)C=C(C)C)C
InChi Key	BATBOVZTQBLKIL-QGZVFWFLSA-N
InChi Code	InChI=1S/C21H22O6/c1-11(2)5-8-17(27-18(25)9-12(3)4)13-10-16(24)19-14(22)6-7-15(23)20(19)21(13)26/h5-7,9-10,17,22-23H,8H2,1-4H3/t17-/m1/s1
Chemical Name	[(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-methylbut-2-enoate
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]. Arnebin-1 promotes angiogenesis by inducing eNOS, VEGF and HIF-1α expression through the PI3K-dependent pathway. Int J Mol Med. 2015 Sep;36(3):685-97. [2]. Arnebin-1 accelerates normal and hydrocortisone-induced impaired wound healing. J Invest Dermatol. 1999 Nov;113(5):773-81.
Additional Infomation	Beta,beta-Dimethylacrylshikonin is a hydroxy-1,4-naphthoquinone. beta,beta-Dimethylacrylshikonin has been reported in Onosma paniculata, Arnebia euchroma, and other organisms with data available. See also: Beta, beta-dimethylacrylshikonin (annotation moved to).

Solubility Data

Solubility (In Vitro)

DMSO : ~12.5 mg/mL (~33.75 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.08 mg/mL (5.62 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.6998 mL	13.4989 mL	26.9978 mL
	5 mM	0.5400 mL	2.6998 mL	5.3996 mL
	10 mM	0.2700 mL	1.3499 mL	2.6998 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.