germacrene A
(1E,5E,8S)-8-isopropenyl-1,5-dimethylcyclodeca-1,5-diene
Identification
| Name | germacrene A |
| IUPAC | (1E,5E,8S)-1,5-dimethyl-8-prop-1-en-2-ylcyclodeca-1,5-diene |
| CAS Number | 28387-44-2 |
| FDA UNII | Search |
| Molecular Formula | C15 H24 |
| Molecular Weight | 204.35628000 |
| Beilstein | 2502353 |
Regulatory
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 |
| Insoluble in | water |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| 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. |
No supplier data available
Potential Uses
Natural Occurrence
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-iso
propenyl-1,5-dimethyl cyclodeca-1,5-diene
(1E,5E,8S)-8-iso
propenyl-1,5-dimethylcyclodeca-1,5-diene
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-Ï 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.