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Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
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| Food Chemicals Codex Listed: | No |
| Boiling Point: | 330.30 °C. @ 760.00 mm Hg (est)
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| Flash Point: | 299.00 °F. TCC ( 148.40 °C. ) (est)
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| logP (o/w): | 4.760 (est) |
| Soluble in: |
| | water, 0.8354 mg/L @ 25 °C (est) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
| Alfa Biotechnology |
| For experimental / research use only. |
| Germacrone 98%
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| BOC Sciences |
| For experimental / research use only. |
| Germacrone 0.95
Odor: characteristic Use: Germacrone isolated from the rhizoma of Curcuma wenyujin. It has anti-tumor activity.
antibacterial; antifungal; |
| Coompo |
| For experimental / research use only. |
| Germacrone from Plants ≥98%
Odor: characteristic Use: Germacrone treatment significantly inhibited cell proliferation, increased lactate dehydrogenase (LDH) release, and induced mitochondrial membrane potential (??m) depolarization in both MCF-7 and MDA-MB-231 cells in a dose-dependent manner. Germacrone induced MDA-MB-231 and MCF-7 cell cycle arrest at the G0/G1 and G2/M phases respectively and induced MDA-MB-231 cell apoptosis. Furthermore, germacrone treatment significantly increased Bok expression and cytochrome c release from mitochondria without affecting Bcl-2, Bcl-xL, Bax, and Bim protein expressions. In addition, germacrone treatment induced caspase-3, 7, 9, PARP cleavage. We concluded that germacrone inhibited the proliferation of breast cancer cell lines by inducing cell cycle arrest and apoptosis through mitochondria-mediated caspase pathway. These results might provide some molecular basis for the anti-tumor activity of Rhizoma curcuma.
Germacrone might be a new potent chemopreventive drug candidate for liver cancer via regulating the expression of proteins related to G2/M cell cycle and apoptosis, and p53 and oxidative damage may play important roles in the inhibition of human hepatoma cells growth by germacrone. |
| Sigma-Aldrich |
| For experimental / research use only. |
| Germacrone analytical standard
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Safety Information:
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
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Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | | natural substances and extractives |
| Recommendation for germacrone usage levels up to: | | | not for fragrance use.
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| Recommendation for germacrone flavor usage levels up to: |
| | not for flavor use.
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Safety References:
References:
| | (3E,7E)-3,7-dimethyl-10-propan-2-ylidenecyclodeca-3,7-dien-1-one |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 6436348 |
| Pubchem (sid): | 135036792 |
| Pherobase: | View |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| 3,7- | cyclodecadien-1-one, 3,7-dimethyl-10-(1-methylethylidene)-, (3E,7E)- | | 3,7- | cyclodecadien-1-one, 3,7-dimethyl-10-(1-methylethylidene)-, (7E)- | | 3,7- | cyclodecadien-1-one, 3,7-dimethyl-10-(1-methylethylidene)-, (E,E)- | | (E,E)-3,7- | dimethyl-10-(1-methyl ethylidene)-3,7-cyclodecadien-1-one | | (3E,7E)-3,7- | dimethyl-10-(propan-2-ylidene)cyclodeca-3,7-dien-1-one | | (7E)-3,7- | dimethyl-10-(propan-2-ylidene)cyclodeca-3,7-dien-1-one | | (3E,7E)-3,7- | dimethyl-10-(propan-2-ylidene)cyclodeca-3,7-dienone | | (3E,7E)-3,7- | dimethyl-10-propan-2-ylidenecyclodeca-3,7-dien-1-one | | (E,E)- | germacra-3,7(11),9-trien-6-one | | (3E,7E)-10-iso | propylidene-3,7-dimethyl-3,7-cyclodecadien-1-one | | (7E)-10-iso | propylidene-3,7-dimethyl-3,7-cyclodecadien-1-one | | (3E,7E)-10-iso | propylidene-3,7-dimethylcyclodeca-3,7-dien-1-one |
Articles:
| PubMed:Germacrone inhibits early stages of influenza virus infection. |
| PubMed:Anti-tumor effect of germacrone on human hepatoma cell lines through inducing G2/M cell cycle arrest and promoting apoptosis. |
| PubMed:Germacrone induces apoptosis in human hepatoma HepG2 cells through inhibition of the JAK2/STAT3 signalling pathway. |
| PubMed:Interactions of sesquiterpenes zederone and germacrone with the human cytochrome P450 system. |
| PubMed:Structural diversity from the transannular cyclizations of natural germacrone and epoxy derivatives: a theoretical-experimental study. |
| PubMed:Impact of fixed-dose combination of germacrone, curdione, and furanodiene on breast cancer cell proliferation. |
| PubMed:Germacrone inhibits the proliferation of breast cancer cell lines by inducing cell cycle arrest and promoting apoptosis. |
| PubMed:Transannular cyclization of (4S,5S)-germacrone-4,5-epoxide into guaiane and secoguaiane-type sesquiterpenes. |
| PubMed:Efficient synthesis of the anticancer β-elemene and other bioactive elemanes from sustainable germacrone. |
| PubMed:[Comparison of content of curdione, curcumol, germacrone and beta-elemene in different varieties of vinegar backed Rhizoma Curcuma]. |
| PubMed:New pathways in transannular cyclization of germacrone [germacra-1(10),4,7(11)-trien-8-one]: evidence regarding a concerted mechanism. |
| PubMed:A HPLC method for the analysis of germacrone in rabbit plasma and its application to a pharmacokinetic study of germacrone after administration of zedoary turmeric oil. |
| PubMed:Structural determination of two new sesquiterpenes biotransformed from germacrone by Mucor alternata. |
| PubMed:Simultaneous determination of multiple sesquiterpenes in Curcuma wenyujin herbal medicines and related products with one single reference standard. |
| PubMed:[Study on effect of Hypericum perforatum on pharmacokinetics of zedoary turmeric oil in compound antiviral preparation]. |
| PubMed:Fast determination of curcumol, curdione and germacrone in three species of Curcuma rhizomes by microwave-assisted extraction followed by headspace solid-phase microextraction and gas chromatography-mass spectrometry. |
| PubMed:Preparative isolation and purification of germacrone and curdione from the essential oil of the rhizomes of Curcuma wenyujin by high-speed counter-current chromatography. |
| PubMed:Further antibacterial Geranium macrorrhizum L. metabolites and synthesis of epoxygermacrones. |
| PubMed:Anti-androgenic effect of sesquiterpenes isolated from the rhizomes of Curcuma aeruginosa Roxb. |
| PubMed:Antibacterial Activity of Rhizome of Curcuma aromatica and Partial Purification of Active Compounds. |
| PubMed:Curcumin-free turmeric exhibits anti-inflammatory and anticancer activities: Identification of novel components of turmeric. |
| PubMed:[The volatile oil of zedoaria IV: TLC densitometric determination of germacrone in the essential oils from Curcuma wenyujin and C. kwangsinensis]. |
| PubMed:Quantitative Analysis and Discrimination of Steamed and Non-Steamed Rhizomes of Curcuma wenyujin by GC-MS and HPLC. |
| PubMed:Germacrone defends labrador tea from browsing by snowshoe hares. |
| PubMed:Geranium macrorrhizum L. (Geraniaceae) essential oil: a potent agent against Bacillus subtilis. |
| PubMed:Anti-cancer properties of terpenoids isolated from Rhizoma Curcumae--a review. |
| PubMed:Analysis and pharmacokinetic study of curdione in Rhizoma Curcumae by UPLC/QTOF/MS. |
| PubMed:Pharmacokinetic study of rhizoma Curcumae oil and rhizoma Curcumae oil-β-cyclodextrin inclusion complex in pigs after oral administration. |
| PubMed:Chemical composition and antimicrobial activity of three essential oils from Curcuma wenyujin. |
| PubMed:Analysis of volatile components in Curcuma rhizome by microemulsion electrokinetic chromatography. |
| PubMed:Zedoary oil (Ezhu You) inhibits proliferation of AGS cells. |
| PubMed:Metabolite profiling of Curcuma species grown in different regions using 1H NMR spectroscopy and multivariate analysis. |
| PubMed:Identification of insecticidal constituents of the essential oil of Curcuma wenyujin rhizomes active against Liposcelis bostrychophila Badonnel. |
| PubMed:[Analysis of compositions of the essential oil from Curcuma aromatica by gas chromatography-mass spectrometry]. |
| PubMed:Sesquiterpenes from Curcuma comosa. |
| PubMed:Antifungal activity and chemical composition of essential oils from Smyrnium olusatrum L. (Apiaceae) from Italy and Portugal. |
| PubMed:[Comparisons of volatile components in different parts of three species of Rhizoma Curcumae]. |
| PubMed:Essential oil of Curcuma longa inhibits Streptococcus mutans biofilm formation. |
| PubMed:Preparative isolation and purification of six volatile compounds from essential oil of Curcuma wenyujin using high-performance centrifugal partition chromatography. |
| PubMed:Anti-tumor potential of ethanol extract of Curcuma phaeocaulis Valeton against breast cancer cells. |
| PubMed:Metabolomics study on quality control and discrimination of three curcuma species based on gas chromatograph-mass spectrometry. |
| PubMed:Compounds isolated from Curcuma aromatica Salisb. inhibit human P450 enzymes. |
| PubMed:[Fingerprints of Curcuma wenyujin by RP-HPLC]. |
| PubMed:Volatile constituents of different parts of Smyrnium olusatrum from Greece. |
| PubMed:Preparation and characterization of nanostructured lipid carriers loaded traditional Chinese medicine, zedoary turmeric oil. |
| PubMed:[Absorption of zedoary oil in rat intestine using in situ single pass perfusion model]. |
| PubMed:[HPLC determination of six components in zedoary turmeric oil and its related injections]. |
| PubMed:Self-nanoemulsifying drug delivery system (SNEDDS) for oral delivery of Zedoary essential oil: formulation and bioavailability studies. |
| PubMed:Molecular genetic and chemical assessment of Rhizoma Curcumae in China. |
| PubMed:Identification and quantitation of eleven sesquiterpenes in three species of Curcuma rhizomes by pressurized liquid extraction and gas chromatography-mass spectrometry. |
| PubMed:[Sesquiterpenes from stems and leaves of Curcuma wenyujin]. |
| PubMed:Chemical composition of essential oil and headspace-solid microextracts from fruits of Myrica gale L. and antifungal activity. |
| PubMed:Essential oil constituents from Japanese and Indian Curcuma aromatica rhizomes. |
| PubMed:Analysis of volatile components of Curcuma sichuanensis X. X. Chen by gas chromatography-mass spectrometry. |
| PubMed:Cytotoxic terpene hydroperoxides from the aerial parts of Aster spathulifolius. |
| PubMed:[The fingerprint of Ezhu by GC-MS]. |
| PubMed:Antiinflammatory effect of Curcuma xanthorrhiza Roxb, and its active principles. |
| PubMed:A novel formulation design about water-insoluble oily drug: preparation of zedoary turmeric oil microspheres with self-emulsifying ability and evaluation in rabbits. |
| PubMed:Medicinal foodstuffs. XXIX. Potent protective effects of sesquiterpenes and curcumin from Zedoariae Rhizoma on liver injury induced by D-galactosamine/lipopolysaccharide or tumor necrosis factor-alpha. |
| PubMed:Chemical constituents of the essential oils of Sideritis scardica Griseb. and Sideritis raeseri Boiss and Heldr. from Bulgaria and Macedonia. |
| PubMed:Biotransformation of terpenoids by mammals, microorganisms, and plant-cultured cells. |
| PubMed:Anti-inflammatory sesquiterpenes from Curcuma zedoaria. |
| PubMed:Optimization of GC-MS conditions based on resolution and stability of analytes for simultaneous determination of nine sesquiterpenoids in three species of Curcuma rhizomes. |
| PubMed:Zedoariae rhizoma and curcumin inhibits platelet-derived growth factor-induced proliferation of human hepatic myofibroblasts. |
| PubMed:Inhibitory effect and action mechanism of sesquiterpenes from Zedoariae Rhizoma on D-galactosamine/lipopolysaccharide-induced liver injury. |
| PubMed:Three non-phenolic diarylheptanoids with anti-inflammatory activity from Curcuma xanthorrhiza. |
| PubMed:[Terpenoids and curcuminoids of the rhizoma of Curcuma xanthorrhiza Roxb]. |
| PubMed:Composition of essential oil of Ledum palustre. |
| PubMed:Simultaneous determination of 11 characteristic components in three species of Curcuma rhizomes using pressurized liquid extraction and high-performance liquid chromatography. |
| PubMed:Study of the preparation of sustained-release microspheres containing zedoary turmeric oil by the emulsion-solvent-diffusion method and evaluation of the self-emulsification and bioavailability of the oil. |
| PubMed:Chemical composition of the essential oil and supercritical CO2 extract of Commiphora myrrha (Nees) Engl. and of Acorus calamus L. |
| PubMed:Essential oil analysis and anticancer activity of leaf essential oil of Croton flavens L. from Guadeloupe. |
| PubMed:[Studies on the chemical constituents of Kaempferia marginata]. |
| PubMed:Chemical variability of the volatile metabolites from the Caribbean corals of the genus Gorgonia. |
| PubMed:[Studies on the chemical constituents of Curcuma kwangsiensis]. |
| PubMed:Experimental study of essential oils from two varieties of cultivated thyme, sesquiterpene Germacron and diterpene Sclareol for cholagogic and choleretic activity. |
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3D/inchi