Identification

Namegermacranolide
IUPAC(3S,3aR,4S,5Z,7S,10Z,11aR)-4,7-dihydroxy-3,6,10-trimethyl-3a,4,7,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one
Molecular FormulaC15 H22 O4
Molecular Weight266.33714000
Nikkaji NumberJ445.275E

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Soluble in water, 1144 mg/L @ 25 °C (est)

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 germacranolide usage levels up tonot for fragrance use.
Recommendation for germacranolide flavor usage levels up tonot for flavor use.

No supplier data available

Potential Uses

None Found

Natural Occurrence

callitris columellaris wood oil australia Data callitris glaucophylla wood oil australia @ 0.60% Data callitris intratropica wood oil australia @ 0.30% Data carduus pycnocephalus centaurea depressa laurus nobilis leaf

Synonyms

(3S,3aR,4S,5Z,7S,10Z,11aR)-4,7- dihydroxy-3,6,10-trimethyl-3a,4,7,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one PubMed: Layer chromatography-bioassays directed screening and identification of antibacterial compounds from Scotch thistle. PubMed: Anti-inflammatory and immunomodulatory activities of Inula cappa roots (Compositae). PubMed: Three new elemanolides from the seeds of Vernonia anthelmintica. PubMed: Antiplasmodial Sesquiterpenoid Lactones from Trichospira verticillata: Structure Elucidation by Spectroscopic Methods and Comparison of Experimental and Calculated ECD Data. PubMed: Investigation of the Anti-Leishmania (Leishmania) infantum Activity of Some Natural Sesquiterpene Lactones. PubMed: Heme-binding activity of methoxyflavones from Pentzia monodiana Maire (Asteraceae). PubMed: Antiprotozoal Activity-Based Profiling of a Dichloromethane Extract from Anthemis nobilis Flowers. PubMed: Isolation, Structure Elucidation, and Absolute Configuration of Highly Oxygenated Germacranolides from Carpesium cernuum. PubMed: A sesquiterpene lactone from Siegesbeckia glabrescens suppresses Hedgehog/Gli-mediated transcription in pancreatic cancer cells. PubMed: Bioherbicidal activity of a germacranolide sesquiterpene dilactone from Ambrosia artemisiifolia L. PubMed: The germacranolide sesquiterpene lactone neurolenin B of the medicinal plant Neurolaena lobata (L.) R.Br. ex Cass inhibits NPM/ALK-driven cell expansion and NF-κB-driven tumour intravasation. PubMed: Melampodium leucanthum, a source of cytotoxic sesquiterpenes with antimitotic activities. PubMed: Centrifugal partition chromatography elution gradient for isolation of sesquiterpene lactones and flavonoids from Anvillea radiata. PubMed: Vibrational circular dichroism (VCD), VCD exciton coupling, and X-ray determination of the absolute configuration of an α,β-unsaturated germacranolide. PubMed: Antiproliferative activity of Artemisia asiatica extract and its constituents on human tumor cell lines. PubMed: Germacranolides and their diversity of Eupatorium heterophyllum collected in P. R. China. PubMed: New sesquiterpenic acids from Inula wissmanniana. PubMed: Effect of different types of sesquiterpene lactones on the maturation of Rhinella arenarum oocytes. PubMed: Isolation, characterization, and in vitro cytotoxicity of new sesquiterpenoids from Achillea clavennae. PubMed: Sesquiterpenes from Neurolaena lobata and their antiproliferative and anti-inflammatory activities. PubMed: Antiprotozoal screening of 60 South African plants, and the identification of the antitrypanosomal germacranolides schkuhrin I and II. PubMed: Secondary metabolites from the aerial parts of Centaurea pannonica (Heuff.) Simonk. from Serbia and their chemotaxonomic importance. PubMed: In-silico Leishmania target selectivity of antiparasitic terpenoids. PubMed: New eudesmenoic acid methyl esters from the seed oil of Jatropha curcas. PubMed: Trilobolide and related sesquiterpene lactones from Laser trilobum possessing immunobiological properties. PubMed: Cytotoxic and NF-κB inhibitory sesquiterpene lactones from Piptocoma rufescens. PubMed: Sesquiterpene lactones from Inula hupehensis inhibit nitric oxide production in RAW264.7 macrophages. PubMed: A new sesquiterpene lactone from Elephantopus tomentosus. PubMed: Screening and HPLC-Based Activity Profiling for New Antiprotozoal Leads from European Plants. PubMed: Sesquiterpenes and other constituents from Dendranthema zawadskii var. latilobum. PubMed: Discovery of GABA(A) receptor modulator aristolactone in a commercial sample of the Chinese herbal drug "Chaihu" (Bupleurum chinense roots) unravels adulteration by nephrotoxic Aristolochia manshuriensis roots. PubMed: Biotransformation of germacranolide from Onopordon leptolepies by Aspergillus niger. PubMed: A facile and efficient four-step enantioselective synthesis of (+)-vernolepin from (+)-minimolide, the major germacranolide of Mikania minima. PubMed: A germacranolide sesquiterpene lactone suppressed inducible nitric oxide synthase by downregulating NF-κB activity. PubMed: An unusual dimeric guaianolide with antiprotozoal activity and further sesquiterpene lactones from Eupatoriumperfoliatum. PubMed: Antileishmanial Germacranolides from Calea zacatechichi. PubMed: Acid rearrangment of epoxy-germacranolides and absolute configuration of 1beta,10alpha-epoxy-salonitenolide. PubMed: Cytotoxic germacranolide sesquiterpenes from the bark of Magnolia kobus. PubMed: Differential proteomic profiling identifies novel molecular targets of paclitaxel and phytoagent deoxyelephantopin against mammary adenocarcinoma cells. PubMed: Chemical and biomolecular characterization of Artemisia umbelliformis Lam., an important ingredient of the alpine liqueur "Genepi". PubMed: Biogenesis of sesquiterpene lactones pseudoguaianolides from germacranolides: theoretical study on the reaction mechanism of terminal biogenesis of 8-epiconfertin. PubMed: Chemical constituents and pharmacological properties of Radix Inulae. PubMed: Sesquiterpene lactones from Staehelina fruticosa. PubMed: Minor sesquiterpene lactones from Centaurea pullata and their antimicrobial activity. PubMed: Cytotoxic germacranolide sesquiterpene from Inula cappa. PubMed: Cytotoxic germacranolide sesquiterpene lactones from Carpesium triste var. manshuricum. PubMed: Cytotoxic germacranolides and acyclic diterpenoides from the seeds of Carpesium triste. PubMed: Quantitative estimation of parthenolide in Tanacetum parthenium (L.) Schultz-Bip. cultivated in Egypt. PubMed: A new germacranolide-type sesquiterpene lactone from Tanacetum santolinoides. PubMed: Isolation and identification of antiplasmodial sesquiterpene lactones from Oncosiphon piluliferum. PubMed: Sesquiterpene lactones from Dimerostemma species (Asteraceae) and in vitro potential anti-inflammatory activities. PubMed: Hepatoprotective sesquiterpene glycosides from Sarcandra glabra. PubMed: Sesquiterpene lactones from Achillea collina J. Becker ex Reichenb. PubMed: Highly oxygenated guaianolides and eudesman-12-oic acids from Balsamorhiza sagittata and Balsamorhiza macrophylla. PubMed: Inhibition of preadipocyte differentiation by germacranolides from Calea urticifolia in 3T3-L1 cells. PubMed: A potent apoptosis-inducing activity of a sesquiterpene lactone, arucanolide, in HL60 cells: a crucial role of apoptosis-inducing factor. PubMed: Germacranolides from Anvillea radiata. PubMed: New sesquiterpene dilactones from Mikania micrantha. PubMed: NMR and x-ray conformational study of artemisiifolin and three other related germacranolides. PubMed: Germacrane derivatives from Santolina pinnata subsp. neapolitana. PubMed: Potent induction of apoptosis by germacranolide sesquiterpene lactones on human myeloid leukemia cells. PubMed: Biosynthesis of anthecotuloide, an irregular sesquiterpene lactone from Anthemis cotula L. (Asteraceae) via a non-farnesyl diphosphate route. PubMed: cis,cis-Germacranolides and melampolides from Mikania thapsoides. PubMed: Antibacterial evaluation of cnicin and some natural and semisynthetic analogues. PubMed: Terpenes from Inula verbascifolia. PubMed: The effect of sesquiterpene lactones on the release of human neutrophil elastase. PubMed: Sesquiterpenes and flavonoid aglycones from a Hungarian taxon of the Achillea millefolium group. PubMed: Seven germacranolides, eupaglehnins A, B, C, D, E, and F, and 2alpha-acetoxyepitulipinolide from Eupatorium glehni. PubMed: Potentiation of 1,25-dihydroxyvitamin D(3)-induced differentiation of human promyelocytic leukemia cells into monocytes by costunolide, a germacranolide sesquiterpene lactone. PubMed: Biosynthesis of costunolide, dihydrocostunolide, and leucodin. Demonstration of cytochrome p450-catalyzed formation of the lactone ring present in sesquiterpene lactones of chicory. PubMed: Germacranolides from Artemisia myriantha and their conformation. PubMed: Chemistry of New Zealand Apiaceae: a rare phenylpropanoid and three new germacrane derivatives from Anisotome lyallii. PubMed: A highly substituted germacranolide from Leontodon cichoraceus. PubMed: Sesquiterpene lactones of Centaurea scoparia. PubMed: A germacranolide and three hydroxybenzyl alcohol derivatives from Hieracium murorum and Crepis bocconi. PubMed: Inhibition of inflammatory cytokine production and lymphocyte proliferation by structurally different sesquiterpene lactones correlates with their effect on activation of NF-kappaB. PubMed: Microbial transformation of pyrethrosin. PubMed: A new germacranolide from Artemisia pallens. PubMed: Germacranolides from Mikania guaco. PubMed: Guaiane dimers and germacranolide from Artemisia caruifolia. PubMed: Germacranolides and a new type of guaianolide from Acanthospermum hispidum. PubMed: Sesquiterpenoids and phenolics from Crepis mollis. PubMed: Further sesquiterpene lactones from Anthemis carpatica. PubMed: Fungicidal activity of natural and synthetic sesquiterpene lactone analogs. PubMed: Sesquiterpene lactones with potential use as natural herbicide models (I): trans,trans-germacranolides. PubMed: Mono- and sesquiterpenes and antifungal constituents from Artemisia species. PubMed: Antimycobacterial evaluation of germacranolides. PubMed: Four new cytotoxic germacranolides from Carpesium divaricatum. PubMed: Sesquiterpene lactone containing Mexican Indian medicinal plants and pure sesquiterpene lactones as potent inhibitors of transcription factor NF-kappaB. PubMed: Antiplasmodial activities and cytotoxic effects of aqueous extracts and sesquiterpene lactones from Neurolaena lobata. PubMed: Conformational analysis and biological activity of leptocarpin and leptocarpin acetate. PubMed: A bioassay for inhibition of serotonin release from bovine platelets. PubMed: Constituents of Michelia Rajaniana. Two new germacranolide amides. PubMed: Constituents of Paramichelia baillonii: a new antitumor germacranolide alkaloid. PubMed: Bisabolone derivatives and sesquiterpene lactones from centaurea species. PubMed: Molecular recognition patterns of sesquiterpene lactones in costus-sensitive patients. PubMed: Antitumor agents, 71. Nudaphantin, a new cytotoxic germacranolide, and elephantopin from Elephantopus nudatus. PubMed: Structure revision and cytotoxicity of the germacranolide, stizolicin, from Stizolophus balsamitus (Asteraceae). PubMed: Germacranolide, Hydroxyverbenon und ent-Kaur-15(16)-en-17,19-disäure aus Helianthus occidentalis var. dowellianus. PubMed: Sesquiterpene Lactones from Aegialophila pumila. PubMed: The effect of sesquiterpene lactones, eupatoriopicrin and hydroxyisonobilin, on the glycolytic metabolism of human lymphocytes. PubMed: Antitumor agents LII: The effects of molephantinin on nucleic acid and protein synthesis of Ehrlich ascites cells. PubMed: Isolation and characterization of the sesquiterpene lactones costunolide, parthenolide, costunolide diepoxide, santamarine, and reynosin from Magnolia grandiflora L. PubMed: Neutron diffraction structure of melampodin: its role in the reclassification of the germacranolides. PubMed: Antitumor agents. II. Tulipinolide, a new germacranolide sesquiterpene, and constunolide. Two cytotoxic substances from Liriodendron tulipifera L.