germacrene A

(1E,5E,8S)-8-isopropenyl-1,5-dimethylcyclodeca-1,5-diene

CAS: 28387-44-2 C15 H24 MW: 204.35628000

Identification

Namegermacrene A
IUPAC(1E,5E,8S)-1,5-dimethyl-8-prop-1-en-2-ylcyclodeca-1,5-diene
CAS Number28387-44-2
FDA UNIISearch
Molecular FormulaC15 H24
Molecular Weight204.35628000
Beilstein2502353

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 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 germacrene A usage levels up tonot for fragrance use.
Recommendation for germacrene A flavor usage levels up tonot for flavor use.

No supplier data available

Potential Uses

None Found

Natural Occurrence

basil shoot oil jambu flower oil brazil @ 3.30% Data lavender oil spike spain @ 0.08% Data levisticum officinale flower oil @ trace% Data levisticum officinale seed oil @ trace% Data marsypianthes chamaedrys (vahl) kuntze oil brazil @ 3.10% Data mikania cordata (burm. f.) b.l. robinson var. cordata leaf oil france @ 1.30% Data palmarosa oil @ trace% Data

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-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.