furanodiene
(Z,E)-8,12-epoxygermacra-1(10),4,7,11-tetraene
 
Notes:
Constit. of Curcuma zedoaria (zedoary)
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      Product(s):
      19912-61-9 Furanodiene >95%
       
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CAS Number: 19912-61-9Picture of molecule3D/inchi
FDA UNII: G0AFT38FJ7
Nikkaji Web: J19.859E
XlogP3-AA: 3.70 (est)
Molecular Weight: 216.32360000
Formula: C15 H20 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
Google Books: Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents: Search
US Patents: Search
EU Patents: Search
Pubchem Patents: Search
PubMed: Search
NCBI: Search
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 305.00 to  307.00 °C. @ 760.00 mm Hg
Vapor Pressure: 0.001000 mmHg @ 25.00 °C. (est)
Flash Point: 279.00 °F. TCC ( 137.22 °C. )
logP (o/w): 5.369 (est)
Soluble in:
 water, 0.1005 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
BOC Sciences
For experimental / research use only.
Furanodiene >95%
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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
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for furanodiene usage levels up to:
 not for fragrance use.
 
Recommendation for furanodiene flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 5317424
National Institute of Allergy and Infectious Diseases: Data
 (5Z,9Z)-3,6,10-trimethyl-4,7,8,11-tetrahydrocyclodeca[b]furan
Chemidplus: 0019912619
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References:
 (5Z,9Z)-3,6,10-trimethyl-4,7,8,11-tetrahydrocyclodeca[b]furan
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 5317424
Pubchem (sid): 135154531
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
KEGG (GenomeNet): C16959
HMDB (The Human Metabolome Database): HMDB36769
FooDB: FDB015711
Typical G.C.
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
EFSA Update of results on the monitoring of furan levels in food: Read Report
EFSA Previous report: Results on the monitoring of furan levels in food: Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food: Read Report
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 protium heptaphyllum (aubl.) march leaf oil brazil @ 2.20%
Data  GC  Search Trop  Picture
 zedoary
Search Trop  Picture
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Synonyms:
(Z,E)-8,12-epoxygermacra-1(10),4,7,11-tetraene
(5E,9Z)-4,7,8,11-tetrahydro-3,6,10-trimethyl cyclodeca(b)furan
(5Z,9Z)-3,6,10-trimethyl-4,7,8,11-tetrahydrocyclodeca[b]furan
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Articles:
PubMed: Cytotoxic Constituents from the Rhizomes of Curcuma zedoaria.
PubMed: Furanodiene, a natural small molecule suppresses metastatic breast cancer cell migration and invasion in vitro.
PubMed: [Transport of PLGA nanoparticles across caco-2/HT29-MTX co-cultured cells].
PubMed: Effects of furanodiene on 95-D lung cancer cells: apoptosis, autophagy and G1 phase cell cycle arrest.
PubMed: Characterization of in vivo and in vitro metabolites of furanodiene in rats by high performance liquid chromatography-electrospray ionization mass spectrometry and nuclear magnetic resonance spectra.
PubMed: Impact of fixed-dose combination of germacrone, curdione, and furanodiene on breast cancer cell proliferation.
PubMed: Curcumin-free turmeric exhibits anti-inflammatory and anticancer activities: Identification of novel components of turmeric.
PubMed: GC/MS analysis of high-performance liquid chromatography fractions from Sophora flavescens and Torilis japonica extracts and their in vitro anti-neosporal effects on Neospora caninum.
PubMed: 2-Bromo-1,6,6-trimethyl-6,7,8,9-tetra-hydro-phenanthro[1,2-b]furan-10,11-dione.
PubMed: Pharmacokinetics and tissue distribution of furanodiene W/O/W multiple emulsions in rats by a fast and sensitive HPLC-APCI-MS/MS method.
PubMed: Furanodiene presents synergistic anti-proliferative activity with paclitaxel via altering cell cycle and integrin signaling in 95-D lung cancer cells.
PubMed: In vitro biological activity of essential oils and isolated furanosesquiterpenes from the neglected vegetable Smyrnium olusatrum L. (Apiaceae).
PubMed: Simultaneous determination of multiple sesquiterpenes in Curcuma wenyujin herbal medicines and related products with one single reference standard.
PubMed: Furanodien-6-one from Commiphora erythraea inhibits the NF-κB signalling and attenuates LPS-induced neuroinflammation.
PubMed: Furanodiene induces endoplasmic reticulum stress and presents antiproliferative activities in lung cancer cells.
PubMed: Furanodiene, a natural product, inhibits breast cancer growth both in vitro and in vivo.
PubMed: Analysis of volatile components in Curcuma rhizome by microemulsion electrokinetic chromatography.
PubMed: Anti-cancer properties of terpenoids isolated from Rhizoma Curcumae--a review.
PubMed: Furanodiene enhances tamoxifen-induced growth inhibitory activity of ERa-positive breast cancer cells in a PPARγ independent manner.
PubMed: A sensitive method for determination of furanodiene in rat plasma using liquid chromatography/tandem mass spectrometry and its application to a pharmacokinetic study.
PubMed: Anti-angiogenic effect of furanodiene on HUVECs in vitro and on zebrafish in vivo.
PubMed: Anti-tumor potential of ethanol extract of Curcuma phaeocaulis Valeton against breast cancer cells.
PubMed: Free radical scavenging activity and characterization of sesquiterpenoids in four species of Curcuma using a TLC bioautography assay and GC-MS analysis.
PubMed: [HPLC determination of six components in zedoary turmeric oil and its related injections].
PubMed: Potential anti-cancer activities of Furanodiene, a Sesquiterpene from Curcuma wenyujin.
PubMed: Induction of apoptosis by furanodiene in HL60 leukemia cells through activation of TNFR1 signaling pathway.
PubMed: Sesquiterpenes from Curcuma comosa.
PubMed: Furanodiene induces G2/M cell cycle arrest and apoptosis through MAPK signaling and mitochondria-caspase pathway in human hepatocellular carcinoma cells.
PubMed: Simultaneous determination of 11 characteristic components in three species of Curcuma rhizomes using pressurized liquid extraction and high-performance liquid chromatography.
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: Identification and quantitation of eleven sesquiterpenes in three species of Curcuma rhizomes by pressurized liquid extraction and gas chromatography-mass spectrometry.
PubMed: Irritant potential of some constituents from oleo-gum-resin of Commiphora myrrha.
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: Essential oil composition of smyrnium olusatrum.
PubMed: Identification and quantitative determination of furanodiene, a heat-sensitive compound, in essential oil by 13C-NMR.
PubMed: Chemical variability of the volatile metabolites from the Caribbean corals of the genus Gorgonia.
PubMed: Local anaesthetic, antibacterial and antifungal properties of sesquiterpenes from myrrh.
PubMed: Inhibitory effect and action mechanism of sesquiterpenes from Zedoariae Rhizoma on D-galactosamine/lipopolysaccharide-induced liver injury.
PubMed: A pyrazoline derivative of eunicin acetate.
PubMed: Constituents of essential oil of Commiphora guidotti.
PubMed: [Constituents of the essential oil of myrrh].
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