germacrone

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

CAS: 6902-91-6 C15 H22 O MW: 218.33954000

Identification

Namegermacrone
IUPAC(3E,7E)-3,7-dimethyl-10-propan-2-ylidenecyclodeca-3,7-dien-1-one
CAS Number6902-91-6
FDA UNIISearch
Molecular FormulaC15 H22 O
Molecular Weight218.33954000
MDL NumberMFCD00210050
Beilstein2047453

Regulatory

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)

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for germacrone usage levels up tonot for fragrance use.
Recommendation for germacrone flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

curcuma amada roxb. rhizome oil @ 0.30% Data selinocarpus angustifolius thyme oil turmeric rhizome zingiber zerumbet (l.) sm. root oil india @ 1.00% Data

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 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.