Curcumenol is a potent CYP3A4 inhibitor (antagonist) with IC50 of 12.6 μM. It is an important extract of Curcuma zedoaria with medicinal value and has neuro-protective (neuro-protection), anti~inflammatory, anti-tumor and hepatoprotective activities. Curcumenol ((+)-Curcumenol) inhibits Akt-mediated NF-κB activation and p38 MAPK signaling pathway in LPS-stimulated BV-2 microglia.

Physicochemical Properties

Molecular Formula	C15H22O2
Molecular Weight	234.339
Exact Mass	234.161
Elemental Analysis	C, 76.88; H, 9.46; O, 13.65
CAS #	19431-84-6
Related CAS #	19431-84-6
PubChem CID	167812
Appearance	White to off-white solid powder
Density	1.1±0.1 g/cm3
Boiling Point	349.3±42.0 °C at 760 mmHg
Flash Point	146.7±22.1 °C
Vapour Pressure	0.0±1.7 mmHg at 25°C
Index of Refraction	1.553
LogP	3.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Heavy Atom Count	17
Complexity	430
Defined Atom Stereocenter Count	4
SMILES	O1[C@@]2(C([H])=C(C([H])([H])[H])[C@]3([H])C([H])([H])C([H])([H])[C@]([H])(C([H])([H])[H])[C@]13C([H])([H])/C/2=C(/C([H])([H])[H])\C([H])([H])[H])O[H]
InChi Key	ISFMXVMWEWLJGJ-NZBPQXDJSA-N
InChi Code	InChI=1S/C15H22O2/c1-9(2)13-8-14-11(4)5-6-12(14)10(3)7-15(13,16)17-14/h7,11-12,16H,5-6,8H2,1-4H3/t11-,12-,14-,15+/m0/s1
Chemical Name	(1S,2S,5S,8R)-2,6-dimethyl-9-propan-2-ylidene-11-oxatricyclo[6.2.1.01,5]undec-6-en-8-ol
Synonyms	Curcumenol
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

Targets	CYP3A4 (IC50 = 36.63 μM); CYP2C9 (IC50 = 75.76 μM)
ln Vitro	Nitric oxide (NO) production, pro-inflammatory cytokines (IL-6) and (TNF-α) and pro-inflammatory protein expression, iNOS, and COX-2 expression are all significantly reduced by curcumenol in response to LPS. Hepatoprotective qualities of curcumenol have also been demonstrated. By preventing the phosphorylation of Akt, curcumenol can reduce the NF-B activity that LPS causes. Its administration significantly reduces the phosphorylation of p38 MAPK caused by LPS, but not JNK or ERK[1]. With an IC50 value of 12.6 1.3 M, curcumenol significantly reduces the activity of CYP3A4. With a Ki of 10.8 μM, kinetic analysis demonstrates curcumenol's competitive inhibition of testosterone 6β-hydroxylation activity (CYP3A4)[2].
ln Vivo	In a sterile 96-well plate with a flat bottom, BV-2 cells are seeded. The following day, the cells are allowed to adhere. The cells are first pretreated with different concentrations of curcumenol for 2 hours, then exposed to LPS (0.4 μg/mL) for 12 to 24 hours.
References	[1].Food Funct . 2015 Nov;6(11):3550-9. [2].Phytother Res . 2010 Aug;24(8):1213-6
Additional Infomation	Curcumenol has been reported in Curcuma xanthorrhiza, Artemisia annua, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO: 46~125 mg/mL (196.3~533.4 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.08 mg/mL (8.88 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 20.8 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: ≥ 2.08 mg/mL (8.88 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 20.8 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: ≥ 2.08 mg/mL (8.88 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	4.2673 mL	21.3365 mL	42.6730 mL
	5 mM	0.8535 mL	4.2673 mL	8.5346 mL
	10 mM	0.4267 mL	2.1337 mL	4.2673 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.