Ingenol is a PKC activator with Ki of 30 μM and anti-tumor activity.

Physicochemical Properties

Molecular Formula	C20H28O5
Molecular Weight	348.4333
Exact Mass	348.193
CAS #	30220-46-3
Related CAS #	Ingenol Mebutate;75567-37-2
PubChem CID	442042
Appearance	White to light yellow solid powder
Density	1.3±0.1 g/cm3
Boiling Point	523.8±50.0 °C at 760 mmHg
Melting Point	153 °C
Flash Point	284.7±26.6 °C
Vapour Pressure	0.0±3.1 mmHg at 25°C
Index of Refraction	1.625
LogP	2.95
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	1
Heavy Atom Count	25
Complexity	707
Defined Atom Stereocenter Count	8
SMILES	C[C@@H]1C[C@@H]2[C@@H](C2(C)C)[C@@H]3C=C([C@H]([C@]4([C@@]1(C3=O)C=C([C@@H]4O)C)O)O)CO
InChi Key	VEBVPUXQAPLADL-POYOOMFHSA-N
InChi Code	InChI=1S/C20H28O5/c1-9-7-19-10(2)5-13-14(18(13,3)4)12(17(19)24)6-11(8-21)16(23)20(19,25)15(9)22/h6-7,10,12-16,21-23,25H,5,8H2,1-4H3/t10-,12+,13-,14+,15+,16-,19+,20-/m1/s1
Chemical Name	(1S,4S,5R,6R,9S,10R,12R,14R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dien-15-one
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
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

ln Vitro	PKC activator ingenol has a Ki of 30 μM. Primary mouse epidermal keratinocytes undergo morphological alterations and are exposed to 1 mM of ingenol, which also induces ornithine decarboxylase activity (1, 3 mM). Intercellular transmission is similarly inhibited by ingenol (125 μM, 250 μM, 500 μM, 1 mM) [1].
References	[1]. Specific binding to protein kinase C by ingenol and its induction of biological responses. Cancer Res. 1992 Jan 1;52(1):202-8.
Additional Infomation	Ingenol is a tetracyclic diterpenoid that is 1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one substituted at positions 5, 5a and 6 by hydroxy groups, positions 1, 1, 7 and 9 by methyl groups, position 4 by a hydroxymethyl group and position 1 by an oxo group (the 1aR,2S,5R,5aR,6S,8aS,9R,10aR diastereomer). It is a tetracyclic diterpenoid and a cyclic terpene ketone. Ingenol has been reported in Euphorbia esula, Euphorbia helioscopia, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~287.00 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (7.18 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 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL 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: ≥ 2.5 mg/mL (7.18 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 25.0 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (7.18 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 25.0 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	2.8700 mL	14.3501 mL	28.7002 mL
	5 mM	0.5740 mL	2.8700 mL	5.7400 mL
	10 mM	0.2870 mL	1.4350 mL	2.8700 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.