Introduction：Basic information about Germacrone CAS 6902-91-6, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Germacrone Basic information
| Product Name: | Germacrone |
| Synonyms: | (E,E)-Germacra-3,7(11),9-trien-6-one;(E,E)-3,7-Dimethyl-10-(1-methylethylidene)-3,7-cyclodecadien-1-one;3,7-Cyclodecadien-1-one, 3,7-dimethyl-10-(1-methylethylidene)-, (E,E)-;3,7-Dimethyl-10-(1-methylethylidene)-3,7-cyclodecadien-1-one;Germacra-3,7(11),9-trien-6-one, (E,E)-;Germacron;trans,trans-3,7-Dimethyl-10-isopropylidene-3,7-cyclodecadien-1-one;(3E,7E)-3,7-Dimethyl-10-isopropylidene-3,7-cyclodecadien-1-one |
| CAS: | 6902-91-6 |
| MF: | C15H22O |
| MW: | 218.33 |
| EINECS: | |
| Product Categories: | chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors |
| Mol File: | 6902-91-6.mol |
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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 |
Germacrone Preparation Products And Raw materials
| Preparation Products | ATRACTYLON-->Cyclohexanemethanol, 4-ethenyl-2-hydroxy-α,α,4-trimethyl-5-(1-methylethenyl)-, (1S,2S,4S,5S)--->Cyclodecene, 6,10-dimethyl-3-(1-methylethylidene)- |
