germacrene A
(1E,5E,8S)-8-isopropenyl-1,5-dimethylcyclodeca-1,5-diene
 
Notes:
None found
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CAS Number: 28387-44-2Picture of molecule3D/inchi
Beilstein Number: 2502353
XlogP3-AA: 4.70 (est)
Molecular Weight: 204.35628000
Formula: C15 H24
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Category: natural substances and extractives
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 281.00 to  282.00 °C. @ 760.00 mm Hg
Vapor Pressure: 0.006000 mmHg @ 25.00 °C. (est)
Flash Point: 235.00 °F. TCC ( 112.78 °C. )
logP (o/w): 6.860 (est)
Soluble in:
 alcohol
 water, 0.009945 mg/L @ 25 °C (est)
Insoluble in:
 water
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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:
 None found
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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 germacrene A usage levels up to:
 not for fragrance use.
 
Recommendation for germacrene A flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 9548706
National Institute of Allergy and Infectious Diseases: Data
 (1E,5E,8S)-1,5-dimethyl-8-prop-1-en-2-ylcyclodeca-1,5-diene
Chemidplus: 0028387442
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References:
 (1E,5E,8S)-1,5-dimethyl-8-prop-1-en-2-ylcyclodeca-1,5-diene
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 9548706
Pubchem (sid): 135145899
Pherobase: View
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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
CHEBI: View
HMDB (The Human Metabolome Database): Search
FooDB: FDB006270
Typical G.C.
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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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
 basil shoot oil
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 jambu flower oil brazil @ 3.30%
Data  GC  Search Trop  Picture
 lavender oil spike spain @ 0.08%
Data  GC  Search Trop  Picture
 levisticum officinale flower oil @ trace%
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 levisticum officinale seed oil @ trace%
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 marsypianthes chamaedrys (vahl) kuntze oil brazil @ 3.10%
Data  GC  Search Trop  Picture
 mikania cordata (burm. f.) b.l. robinson var. cordata leaf oil france @ 1.30%
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 palmarosa oil @ trace%
Data  GC  Search Trop  Picture
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Synonyms:
1,5-cyclodecadiene, 1,5-dimethyl-8-(1-methylethenyl)-, (1E,5E,8S)-
(1E,5E,8S)-1,5-dimethyl-8-(1-methyl ethenyl)-1,5-cyclodecadiene
(S-(E,E))-1,5-dimethyl-8-(1-methyl ethenyl)-1,5-cyclodecadiene
(1E,5E,8S)-1,5-dimethyl-8-(1-methylethenyl)-1,5-cyclodecadiene
[S-(E,E)]-1,5-dimethyl-8-(1-methylethenyl)-1,5-cyclodecadiene
(1E,5E,8S)-1,5-dimethyl-8-(prop-1-en-2-yl)cyclodeca-1,5-diene
(1E,5E,8S)-1,5-dimethyl-8-prop-1-en-2-ylcyclodeca-1,5-diene
(1E,4E,7betaH)-germacra-1(10),4,11(12)-triene
(E,E)-germacra-3,9,11-triene
(-)-germacrene A
(1E,5E,8S)-8-isopropenyl-1,5-dimethyl cyclodeca-1,5-diene
(1E,5E,8S)-8-isopropenyl-1,5-dimethylcyclodeca-1,5-diene
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Articles:
PubMed: Cytochrome P450s from Cynara cardunculus L. CYP71AV9 and CYP71BL5, catalyze distinct hydroxylations in the sesquiterpene lactone biosynthetic pathway.
PubMed: Chemical composition of the essential oil of Croton bonplandianus from India.
PubMed: Expression, purification and activity assay of a patchoulol synthase cDNA variant fused to thioredoxin in Escherichia coli.
PubMed: Studies on the expression of linalool synthase using a promoter-β-glucuronidase fusion in transgenic Artemisia annua.
PubMed: Studies on the expression of sesquiterpene synthases using promoter-β-glucuronidase fusions in transgenic Artemisia annua L.
PubMed: Analysis of Cleistopholis patens leaf and trunk bark oils using combined GC- flame ionisation detection, GC-retention index, GC-MS and (13) C-NMR.
PubMed: Chemoenzymatic preparation of germacrene analogues.
PubMed: The organ-specific expression of terpene synthase genes contributes to the terpene hydrocarbon composition of chamomile essential oils.
PubMed: Genetic mapping and characterization of the globe artichoke (+)-germacrene A synthase gene, encoding the first dedicated enzyme for biosynthesis of the bitter sesquiterpene lactone cynaropicrin.
PubMed: Analysis of exhaled volatile compounds following acute superior mesenteric artery occlusion in a pilot rat study.
PubMed: Reconstitution of the costunolide biosynthetic pathway in yeast and Nicotiana benthamiana.
PubMed: Probing eudesmane cation-π interactions in catalysis by aristolochene synthase with non-canonical amino acids.
PubMed: Biosynthesis and localization of parthenolide in glandular trichomes of feverfew (Tanacetum parthenium L. Schulz Bip.).
PubMed: Lettuce costunolide synthase (CYP71BL2) and its homolog (CYP71BL1) from sunflower catalyze distinct regio- and stereoselective hydroxylations in sesquiterpene lactone metabolism.
PubMed: Relative expression of genes of terpene metabolism in different tissues of Artemisia annua L.
PubMed: Inhibition of (+)-aristolochene synthase with iminium salts resembling eudesmane cation.
PubMed: Efficient functional analysis system for cyanobacterial or plant cytochromes P450 involved in sesquiterpene biosynthesis.
PubMed: A chicory cytochrome P450 mono-oxygenase CYP71AV8 for the oxidation of (+)-valencene.
PubMed: Genome mining in Streptomyces avermitilis: cloning and characterization of SAV_76, the synthase for a new sesquiterpene, avermitilol.
PubMed: Identification and functional characterization of a new sunflower germacrene A synthase (HaGAS3).
PubMed: Biochemical conservation and evolution of germacrene A oxidase in asteraceae.
PubMed: Essential oils from two Lantana species with antimycobacterial activity.
PubMed: Intermediacy of eudesmane cation during catalysis by aristolochene synthase.
PubMed: Identification, functional characterization and developmental regulation of sesquiterpene synthases from sunflower capitate glandular trichomes.
PubMed: Diversity of sesquiterpene synthases in the basidiomycete Coprinus cinereus.
PubMed: 6- and 14-Fluoro farnesyl diphosphate: mechanistic probes for the reaction catalysed by aristolochene synthase.
PubMed: Cuticular hydrocarbons and soldier defense secretions of Reticulitermes in southern California: a critical analysis of the taxonomy of the genus in North America.
PubMed: Terpene biosynthesis in glandular trichomes of hop.
PubMed: Identification of sesquiterpene synthases from Nostoc punctiforme PCC 73102 and Nostoc sp. strain PCC 7120.
PubMed: Stereochemistry of eudesmane cation formation during catalysis by aristolochene synthase from Penicillium roqueforti.
PubMed: [Advances in sesquiterpene synthases cyclases of Artemisia annua].
PubMed: Bioactivity and chemical composition of the leaf essential oils of Zanthoxylum rhoifolium and Zanthoxylum setulosum from Monteverde, Costa Rica.
PubMed: Synthetic efficiency in enzyme mechanisms involving carbocations: aristolochene synthase.
PubMed: Interception of the enzymatic conversion of farnesyl diphosphate to 5-epi-aristolochene by using a fluoro substrate analogue: 1-fluorogermacrene A from (2E,6Z)-6-fluorofarnesyl diphosphate.
PubMed: Conformational Analysis of (+)-Germacrene A by Variable Temperature NMR and NOE Spectroscopy.
PubMed: Aristolochene synthase-catalyzed cyclization of 2-fluorofarnesyl-diphosphate to 2-fluorogermacrene A.
PubMed: The diverse sesquiterpene profile of patchouli, Pogostemon cablin, is correlated with a limited number of sesquiterpene synthases.
PubMed: From terpenoids to aliphatic acids: further evidence for late-instar switch in osmeterial defense as a characteristic trait of swallowtail butterflies in the tribe papilionini.
PubMed: Stabilisation of transition states prior to and following eudesmane cation in aristolochene synthase.
PubMed: Isoprenoid biosynthesis in Artemisia annua: cloning and heterologous expression of a germacrene A synthase from a glandular trichome cDNA library.
PubMed: Silencing of a germin-like gene in Nicotiana attenuata improves performance of native herbivores.
PubMed: Stereochemistry and deuterium isotope effects associated with the cyclization-rearrangements catalyzed by tobacco epiaristolochene and hyoscyamus premnaspirodiene synthases, and the chimeric CH4 hybrid cyclase.
PubMed: Point mutation of (+)-germacrene A synthase from Ixeris dentata.
PubMed: Dual role for phenylalanine 178 during catalysis by aristolochene synthase.
PubMed: Aristolochene synthase: mechanistic analysis of active site residues by site-directed mutagenesis.
PubMed: Nitrogen supply influences herbivore-induced direct and indirect defenses and transcriptional responses in Nicotiana attenuata.
PubMed: Sesquiterpenes of the liverwort Scapania undulata.
PubMed: Terpenoid metabolism in wild-type and transgenic Arabidopsis plants.
PubMed: Electrophysiological responses of female and male Hypsipyla grandella (Zeller) to Swietenia macrophylla essential oils.
PubMed: Evidence for differential folding of farnesyl pyrophosphate in the active site of aristolochene synthase: a single-point mutation converts aristolochene synthase into an (E)-beta-farnesene synthase.
PubMed: Interspecific variation in terpenoid composition of defensive secretions of European Reticulitermes termites.
PubMed: Monitoring and fast detection of mycotoxin-producing fungi based on headspace solid-phase microextraction and headspace sorptive extraction of the volatile metabolites.
PubMed: [GC-MS analysis and inhibitory activity of the essential oil extracted from the leaves of Lindera communis].
PubMed: [Chemical constituents of the essential oil from the fruits of Lindera glauca and its antifungal activities].
PubMed: Probing sesquiterpene hydroxylase activities in a coupled assay with terpene synthases.
PubMed: Germacrene A is a product of the aristolochene synthase-mediated conversion of farnesylpyrophosphate to aristolochene.
PubMed: (+)-(10R)-Germacrene A synthase from goldenrod, Solidago canadensis; cDNA isolation, bacterial expression and functional analysis.
PubMed: Pentalenene synthase. Analysis of active site residues by site-directed mutagenesis.
PubMed: Cloning and expression of sesquiterpene synthase genes from lettuce (Lactuca sativa L.).
PubMed: Isolation and characterization of two germacrene A synthase cDNA clones from chicory.
PubMed: Germacrenes from fresh costus roots.
PubMed: Correspondence of soldier defense secretion mixtures with cuticular hydrocarbon phenotypes for chemotaxonomy of the termite genus Reticulitermes in North America.
PubMed: Biosynthesis of germacrene A carboxylic acid in chicory roots. Demonstration of a cytochrome P450 (+)-germacrene a hydroxylase and NADP+-dependent sesquiterpenoid dehydrogenase(s) involved in sesquiterpene lactone biosynthesis.
PubMed: (+)-Germacrene A biosynthesis . The committed step in the biosynthesis of bitter sesquiterpene lactones in chicory
PubMed: Germacrene C synthase from Lycopersicon esculentum cv. VFNT cherry tomato: cDNA isolation, characterization, and bacterial expression of the multiple product sesquiterpene cyclase.
PubMed: Chemical nature of larval osmeterial secretions of papilionid butterflies in the generaParnassius, Sericinus andPachliopta.
PubMed: Sesquiterpenes in the frontal gland secretions of nasute soldier termites from New Guinea.
PubMed: Constituents of osmeterial secretion of pre-final instar larvae of citrus swallowtail,Papilio demodocus (Esper) (Lepidoptera: Papilionidae).
PubMed: Further studies of the terpenoid content in the gorgonian Eunicea succinea: 12,13-bisepieupalmerin, a new cembranolide.
PubMed: Larval osmeterial secretions of the swallowtails (Papilio).
PubMed: Chemical composition of the frontal gland secretion ofSyntermes soldiers (Isoptera, Termitidae).
PubMed: Sesquiterpene progenitor, germacrene A: an alarm pheromone in aphids.
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