trans,trans-3,7-Dimethyl-10-isopropylidene-3,7-cyclodecadien-1-one
Germacrone
CAS: 6902-91-6
Molecular Formula: C15H22O
trans,trans-3,7-Dimethyl-10-isopropylidene-3,7-cyclodecadien-1-one - Names and Identifiers
trans,trans-3,7-Dimethyl-10-isopropylidene-3,7-cyclodecadien-1-one - Physico-chemical Properties
| Molecular Formula | C15H22O |
| Molar Mass | 218.33 |
| Density | 0.9908 g/cm3 |
| Melting Point | 55-58°C |
| Boling Point | 153-157 °C(Press: 13 Torr) |
| Flash Point | 148.4°C |
| Solubility | Soluble in methanol, ethanol, DMSO and other organic solvents |
| Vapor Presure | 0.000168mmHg at 25°C |
| Appearance | White needle crystal |
| Color | White to Off-White |
| Maximum wavelength(λmax) | ['309nm(MeOH)(lit.)'] |
| BRN | 2047453 |
| Storage Condition | 2-8°C |
| Stability | Light Sensitive |
| Refractive Index | 1.485 |
| MDL | MFCD00210050 |
| Physical and Chemical Properties | White needle-like crystals, soluble in methanol, ethanol, DMSO and other organic solvents, derived from zedoary. |
trans,trans-3,7-Dimethyl-10-isopropylidene-3,7-cyclodecadien-1-one - Risk and Safety
| Safety Description | S23 - Do not breathe vapour. S24/25 - Avoid contact with skin and eyes. |
| RTECS | GU2210000 |
| HS Code | 29142990 |
trans,trans-3,7-Dimethyl-10-isopropylidene-3,7-cyclodecadien-1-one - Reference
| Reference Show more | 1. Song Min, Gu Liyun, Xu Jinguo, etc. Study on the correlation between the UFLC-Q-TOF-MS chromatographic peak and the inhibition of tail thrombosis in mice before and after the processing of vinegar [J]. Chinese Journal of Traditional Chinese Medicine, 44 Vol. 12, 2019-2518 pages, MEDLINE ISTIC PKU CSCD CA BP. 2. Hao Min, Lu, Lin, Mao, Chun, Qin, et al. UPLC fingerprint and multi-component content determination of three processed rhizome products of Curcuma wenyujin [J]. Chinese Journal of Traditional Chinese Medicine, 2018, 43(11). 3. Yu, Ziqiang, et al. "Germacrone induced as well as protective autophagy in human prostate cancer cells." Cancer management and research 12 (2020): 4009.https://dx.doi.org/10.2147/CMAR.S250522 4. [IF=2.727] Shen Song et al."Spectrum-effect relationship analysis by binary chromatographic fingerprint to identify components responsible for the antibacterial activity of the essential oil from Curcumae wenyujin."Int J Food Prop. 2018;21(1):546-556 5. [IF=4.821] Le Wang et al."HPLC fingerprint and UV-Vis spectroscopy coupled with chemometrics for Curcumae radix species discrimination and three bioactive compounds prediction."Microchem J. 2021 Jul;166:106254 6. [IF=4.098] Le Wang et al."Fast discrimination and quantification analysis of Curcumae Radix from four botanical origins using NIR spectroscopy coupled with chemometrics tools."Spectrochim Acta A. 2021 Jun;254:119626 7. [IF=2.952] Yang Zhao et al."Germacrone induces lung cancer cell apoptosis and cell cycle arrest via the Akt/MDM2/p53 signaling pathway."Mol Med Rep. 2021 Jun;23(6):1-9 8. [IF=2.886] Ziqiang Yu et al."Germacrone Induces Apoptosis as Well as Protective Autophagy in Human Prostate Cancer Cells."Cancer Manag Res. 2020; 12: 4009-4016 9. [IF=3.269] Mingqin Lin et al."Germacrone alleviates okadaic acid-induced neurotoxicity in PC12 cells via M1 muscarinic receptor-mediated Galphaq (Gq)/phospholipase C beta (PLCβ)/ protein kinase C (PKC) signaling."Bioengineered. 2022;13(3):4898-4910 |
trans,trans-3,7-Dimethyl-10-isopropylidene-3,7-cyclodecadien-1-one - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| function | Germacrone is a kind of monocyclic sesquiterpene compound, which is also called rhododendron ketone, haloperazone, etc, it is found in plants such as the seedling family, the family of rhododendron and Zingiberaceae. A large number of studies have shown that germacrone can inhibit the proliferation of liver cancer cells, breast cancer cells, lung cancer cells and glioma cells, promote apoptosis, and has anti-tumor effect, and showed quality dependence. Its anti-tumor mechanism is mainly to induce cancer cell apoptosis and block cell cycle. |
| pharmacokinetics | in recent 10 years, researchers have studied the pharmacokinetics in rats and rabbits by high performance liquid chromatography, it was found that the linear range of germacrone in plasma was between 0.1~15 μg/mL. The precision, stability and recovery rate of the method were in line with the requirements of biological sample determination. The study found that the absorption of germacrone in the gastrointestinal tract was slow, and the blood concentration reached the highest value after 1H of administration, the elimination half-life of the main Pharmacokinetic parameter is about 22 h, and it is concluded that germacrone is a slow elimination drug; AUC is 0.739 μg/h/L, and the plasma concentration-time curve of germacrone was in accordance with the two-compartment model. The maximum plasma concentration of germacrone was (6.557±0.52) μg/mL. The pharmacokinetics of germacrone in rat plasma was studied by high performance liquid chromatography (HPLC). It was also found that the endogenous substances in plasma had no effect on the determination. Pharmacokinetics of male rabbits after intravenous injection of germacrone was studied by RP-HPLC, it was found that the dose of germacrone in rabbit plasma after intravenous injection was linear in the range of 3.2~9.6g/mL, and the plasma concentration-time curve was fitted to a one or two compartment intravenous injection model. |
| biological activity | Germacrone was extracted from turmeric and inhibited influenza virus infection by virus. |
| Target | Influenza virus |
| Use | germacrone has antitussive and antiasthmatic effects. for content determination/identification/pharmacological experiments. Pharmacological Efficacy: preparation of treatment or prevention of influenza Virus drugs, with antitussive, Antiasthmatic effect |
Last Update：2024-04-09 21:01:54
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View History
trans,trans-3,7-Dimethyl-10-isopropylidene-3,7-cyclodecadien-1-one
argutone
1-octene-3-one
2,3-DINITROBENZOIC ACID
2,2-Cryptand
Cumene hydroperoxide
disodium dodecyl(sulphonatophenoxy)benzenesulphonate
阿昔洛韦侧链
葡萄糖酸氯已定
9H-Xanthen-9-one, 2-(acetyloxy)-1,6,8-trimethoxy-
argutone
1-octene-3-one
2,3-DINITROBENZOIC ACID
2,2-Cryptand
Cumene hydroperoxide
disodium dodecyl(sulphonatophenoxy)benzenesulphonate
阿昔洛韦侧链
葡萄糖酸氯已定
9H-Xanthen-9-one, 2-(acetyloxy)-1,6,8-trimethoxy-