Germacrone Chemical Properties

Melting point:

55-58 °C

Boiling point:

153-157 °C(Press: 13 Torr)

Density 

0.9908 g/cm3

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

form 

Solid

color 

White to Off-White

λmax

309nm(MeOH)(lit.)

BRN 

2047453

Stability:

Light Sensitive

LogP

4.760 (est)

CAS DataBase Reference

6902-91-6

NIST Chemistry Reference

3,7-Cyclodecadien-1-one, 3,7-dimethyl-10-(1-methylethylidene)-, (e,e)-(6902-91-6)

Safety Information

Safety Statements 

23-24/25

RTECS 

GU2210000

HS Code 

29142990

Germacrone Usage And Synthesis

Description

Germacrone is a sesquiterpene that has been found in gingeraceae plants and has diverse biological activities. It inhibits pseudorabies virus (PRV) replication in Vero cells when used at concentrations ranging from 10 to 150 μM. Germacrone (50-250 μM) enhances cytotoxicity and apoptosis induced by doxorubicin in doxorubicin-resistant MCF-7/adr cells. In vivo, germacrone (5, 10, and 20 mg/kg) reduces body weight gain, visceral fat pad weight, serum insulin and plasma glucose levels, and hepatic lipid levels in a mouse model of high-fat diet-induced obesity. It decreases brain malondialdehyde (MDA) levels and activity of superoxide dismutase (SOD) and glutathione peroxidase (GPX), as well as reduces infarct volume in a rat model of ischemia-reperfusion injury induced by middle cerebral artery occlusion (MCAO).

Chemical Properties

White needle-shaped crystals, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Curcuma zedoaria.

Uses

Germacrone is an antiviral isolate of Geranium macrorrhizum which inhibits and prevents early stage influenza virus infection. It also inhibits the proliferation of glioma cells by promoting apoptosis.

Definition

ChEBI: (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.

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 3489, 1983 DOI: 10.1016/S0040-4039(00)86020-7

Hazard

A poison by ingestion

Safety Profile

A poison by ingestion. When heated to decomposition it emits acrid smoke and irritating vapors.

References

[1] WANTING HE. Antiviral Activity of Germacrone against Pseudorabies Virus in Vitro[J]. Pathogens, 2019. DOI: 10.3390/pathogens8040258
[2] XIAO-HONG XIE. Germacrone reverses Adriamycin resistance through cell apoptosis in multidrug-resistant breast cancer cells.[J]. Experimental and therapeutic medicine, 2014, 8 5: 1611-1615. DOI: 10.3892/etm.2014.1932
[3] YUAN-RI GUO S C. Germacrone Attenuates Hyperlipidemia and Improves Lipid Metabolism in High-Fat Diet-Induced Obese C57BL/6J Mice.[J]. Journal of medicinal food, 2017, 20 1 1: 46-55. DOI: 10.1089/jmf.2016.3811
[4] TIANHUI WU. Germacrone attenuates cerebral ischemia/reperfusion injury in rats via antioxidative and antiapoptotic mechanisms[J]. Journal of cellular biochemistry, 2019, 120 11: 18901-18909. DOI: 10.1002/jcb.29210

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