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germacrone
(E,E)-3,7-dimethyl-10-(1-methyl ethylidene)-3,7-cyclodecadien-1-one

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Name:(3E,7E)-3,7-dimethyl-10-propan-2-ylidenecyclodeca-3,7-dien-1-one
CAS Number: 6902-91-6Picture of molecule3D/inchi
Beilstein Number:2047453
MDL:MFCD00210050
XlogP3-AA:3.50 (est)
Molecular Weight:218.33954000
Formula:C15 H22 O
NMR Predictor:Predict (works with chrome or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 330.30 °C. @ 760.00 mm Hg (est)
Flash Point: 299.00 °F. TCC ( 148.40 °C. ) (est)
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:
None found
 
Suppliers:
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
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category: natural substances and extractives
Recommendation for germacrone usage levels up to:
 not for fragrance use.
 
Recommendation for germacrone flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :6436348
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(3E,7E)-3,7-dimethyl-10-propan-2-ylidenecyclodeca-3,7-dien-1-one
Chemidplus:0006902916
RTECS:GU2210000 for cas# 6902-91-6
 
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:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
KEGG (GenomeNet):C16966
HMDB (The Human Metabolome Database):Search
FooDB:FDB005347
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
RSC Learn Chemistry:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 curcuma amada roxb. rhizome oil @ 0.30%
Data GC Search Trop Picture
 selinocarpus angustifolius
Search Trop Picture
 thyme oil
Search Trop Picture
 turmeric rhizome
Search Trop Picture
 zingiber zerumbet (l.) sm. root oil india @ 1.00%
Data GC Search Trop Picture
 
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-isopropylidene-3,7-dimethyl-3,7-cyclodecadien-1-one
(7E)-10-isopropylidene-3,7-dimethyl-3,7-cyclodecadien-1-one
(3E,7E)-10-isopropylidene-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.
 
Notes:
isolated from curcuma wenyujin.
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