Germacrone is found in turmeric and inhibits influenza virus infection.

Physicochemical Properties

Molecular Formula	C15H22O
Molecular Weight	218.34
Exact Mass	218.167
CAS #	6902-91-6
PubChem CID	6436348
Appearance	White to off-white solid powder
Density	0.9±0.1 g/cm3
Boiling Point	330.3±42.0 °C at 760 mmHg
Melting Point	55-58ºC
Flash Point	148.4±18.7 °C
Vapour Pressure	0.0±0.7 mmHg at 25°C
Index of Refraction	1.485
LogP	4.76
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	0
Heavy Atom Count	16
Complexity	363
Defined Atom Stereocenter Count	0
SMILES	C/C/1=C\CC(=C(C)C)C(=O)C/C(=C/CC1)/C
InChi Key	CAULGCQHVOVVRN-SWZPTJTJSA-N
InChi Code	InChI=1S/C15H22O/c1-11(2)14-9-8-12(3)6-5-7-13(4)10-15(14)16/h7-8H,5-6,9-10H2,1-4H3/b12-8+,13-7+
Chemical Name	(3E,7E)-3,7-dimethyl-10-propan-2-ylidenecyclodeca-3,7-dien-1-one
Synonyms	Germacron Germacrone
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]. Germacrone inhibits early stages of influenza virus infection. Antiviral Res. 2013 Dec;100(3):578-88.

Additional Infomation

(E,E)-germacrone is a germacrane sesquiterpenoid that has formula C15H22O. It is a natural product found in traditional medicinal plants of the family Zingiberaceae. The compound exhibits a range of pharmacological activities including anti-inflammatory, anticancer, antiviral, anti-androgenic, antioxidant, antimicrobial, antifungal, neuroprotective and insecticidal activities. It has a role as a volatile oil component, an antiviral agent, an insecticide, an anti-inflammatory agent, an antioxidant, an antineoplastic agent, an apoptosis inducer, an autophagy inducer, an antimicrobial agent, an androgen antagonist, a neuroprotective agent, a plant metabolite, an antifungal agent, an antitussive, an antifeedant and a hepatoprotective agent. It is a germacrane sesquiterpenoid and an olefinic compound. Germacrone has been reported in Rhododendron dauricum, Curcuma xanthorrhiza, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO : 44 ~100 mg/mL (201.52 ~458.02 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (11.45 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 (11.45 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 (11.45 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. Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (11.45 mM)  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	4.5800 mL	22.9001 mL	45.8001 mL
	5 mM	0.9160 mL	4.5800 mL	9.1600 mL
	10 mM	0.4580 mL	2.2900 mL	4.5800 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.