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Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
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| Food Chemicals Codex Listed: | No |
| Boiling Point: | 281.00 to 282.00 °C. @ 760.00 mm Hg
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| Vapor Pressure: | 0.006000 mmHg @ 25.00 °C. (est) |
| Flash Point: | 235.00 °F. TCC ( 112.78 °C. )
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| logP (o/w): | 6.860 (est) |
| Soluble in: |
| | alcohol | | | water, 0.009945 mg/L @ 25 °C (est) |
| Insoluble in: |
| | water |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
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Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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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.
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| Recommendation for germacrene A flavor usage levels up to: |
| | not for flavor use.
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Safety References:
References:
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
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 |
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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3D/inchi