| Name: | (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 |
| CAS not found | NF0466 | 3D/inchi
|
| Nikkaji Web: | J445.275E |
| XlogP3-AA: | 0.70 (est) |
| Molecular Weight: | 266.33714000 |
| Formula: | C15 H22 O4 |
| NMR Predictor: | Predict (works with chrome, Edge or firefox) |
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 |
| Soluble in: |
| | water, 1144 mg/L @ 25 °C (est) |
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 germacranolide usage levels up to: | | | not for fragrance use.
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| Recommendation for germacranolide flavor usage levels up to: |
| | not for flavor use.
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Safety References:
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| Laboratory Chemical Safety Summary :101616641 |
| (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 |
References:
| | (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 |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 101616641 |
| Pubchem (cas): | NF0466 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
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 |
Articles:
| 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. |
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