Germacrone
Synonym(s):(E,E)-Germacra-3,7(11),9-trien-6-one;trans,trans-3,7-Dimethyl-10-isopropylidene-3,7-cyclodecadien-1-one
- CAS NO.:6902-91-6
- Empirical Formula: C15H22O
- Molecular Weight: 218.33
- MDL number: MFCD00210050
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-19 20:33:22
What is Germacrone?
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).
The Uses of Germacrone
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.
Properties of Germacrone
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 |
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 for Germacrone
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P337+P313:IF eye irritation persists: Get medical advice/attention. |
Computed Descriptors for Germacrone
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