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methyl farnesoate
2,6,10-dodecatrienoic acid, 3,7,11-trimethyl-, methyl ester

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Name:methyl 3,7,11-trimethyldodeca-2,6,10-trienoate
CAS Number: 10485-70-8Picture of molecule3D/inchi
FDA UNII: Search
Nikkaji Web:J140.347H
MDL:MFCD08061871
XlogP3-AA:5.30 (est)
Molecular Weight:250.38162000
Formula:C16 H26 O2
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 336.00 to 337.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure:0.000115 mmHg @ 25.00 °C. (est)
Flash Point: 323.00 °F. TCC ( 161.70 °C. ) (est)
logP (o/w): 5.513 (est)
Soluble in:
 alcohol
 water, 0.1018 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
(E,E)-Methyl Farnesoate
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for methyl farnesoate usage levels up to:
 not for fragrance use.
 
Recommendation for methyl farnesoate flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5275508
National Institute of Allergy and Infectious Diseases:Data
methyl 3,7,11-trimethyldodeca-2,6,10-trienoate
Chemidplus:0010485708
 
References:
 methyl 3,7,11-trimethyldodeca-2,6,10-trienoate
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5275508
Pubchem (sid):135077393
Pherobase:View
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C16503
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
2,6,10-dodecatrienoic acid, 3,7,11-trimethyl-, methyl ester
 farnesyl methyl ester
 methyl 3,7,11-trimethyldodeca-2,6,10-trienoate
3,7,11-trimethyl-2,6,10-dodecatrienoic acid methyl ester
 

Articles:

PubMed:Methyl farnesoate synthesis is necessary for the environmental sex determination in the water flea Daphnia pulex.
PubMed:Evolution. All in the (bigger) family.
PubMed:Genomic analysis of the interaction between pesticide exposure and nutrition in honey bees (Apis mellifera).
PubMed:Identification of putative ecdysteroid and juvenile hormone pathway genes in the shrimp Neocaridina denticulata.
PubMed:The HR97 (NR1L) group of nuclear receptors: a new group of nuclear receptors discovered in Daphnia species.
PubMed:Insulin receptor-mediated nutritional signalling regulates juvenile hormone biosynthesis and vitellogenin production in the German cockroach.
PubMed:Juvenile hormone biosynthesis gene expression in the corpora allata of honey bee (Apis mellifera L.) female castes.
PubMed:Identification of methyl farnesoate from the hemolymph of insects.
PubMed:A farnesoic acid O-methyltransferase (FAMeT) from Exopalaemon carinicauda is responsive to Vibrio anguillarum and WSSV challenge.
PubMed:Sesquiterpene action, and morphogenetic signaling through the ortholog of retinoid X receptor, in higher Diptera.
PubMed:Aspergillus nidulans synthesize insect juvenile hormones upon expression of a heterologous regulatory protein and in response to grazing by Drosophila melanogaster larvae.
PubMed:Farnesyl phosphatase, a Corpora allata enzyme involved in juvenile hormone biosynthesis in Aedes aegypti.
PubMed:Effect of juvenoids on predator-induced polyphenism in the water flea, Daphnia pulex.
PubMed:A mutation in the receptor Methoprene-tolerant alters juvenile hormone response in insects and crustaceans.
PubMed:A transgenerational endocrine signaling pathway in Crustacea.
PubMed:How are comparative genomics and the study of microRNAs changing our views on arthropod endocrinology and adaptations to the environment?
PubMed:Crystal structure of silkworm Bombyx mori JHBP in complex with 2-methyl-2,4-pentanediol: plasticity of JH-binding pocket and ligand-induced conformational change of the second cavity in JHBP.
PubMed:Post-embryonic transcriptomes of the prawn Macrobrachium rosenbergii: multigenic succession through metamorphosis.
PubMed:Effect of methyl farnesoate on the change of the reproduction mode in Moina macrocopa (Cladocera).
PubMed:Ligand binding pocket function of Drosophila USP is necessary for metamorphosis.
PubMed:Induction of male production in clones of Daphnia pulex by the juvenoid hormone methyl farnesoate under short photoperiod.
PubMed:Effects of honey bee (Apis mellifera L.) queen insemination volume on worker behavior and physiology.
PubMed:FoxO inhibits juvenile hormone biosynthesis and vitellogenin production in the German cockroach.
PubMed:Vitellogenin-like proteins in the freshwater amphipod Gammarus fossarum (Koch, 1835): functional characterization throughout reproductive process, potential for use as an indicator of oocyte quality and endocrine disruption biomarker in males.
PubMed:Defining the contribution of select neuropeptides and their receptors in regulating sesquiterpenoid biosynthesis by Drosophila melanogaster ring gland/corpus allatum through RNAi analysis.
PubMed:The CHH-superfamily of multifunctional peptide hormones controlling crustacean metabolism, osmoregulation, moulting, and reproduction.
PubMed:Farnesoic acid and methyl farnesoate production during lobster reproduction: possible functional correlation with retinoid X receptor expression.
PubMed:Molecular cloning and sequence of retinoid X receptor in the green crab Carcinus maenas: a possible role in female reproduction.
PubMed:cis- and trans-Regulation of miR163 and target genes confers natural variation of secondary metabolites in two Arabidopsis species and their allopolyploids.
PubMed:Frequency and inheritance of non-male producing clones in Daphnia magna: evolution towards sex specialization in a cyclical parthenogen?
PubMed:Two juvenile hormone esterase-like carboxylesterase cDNAs from a Pandalus shrimp (Pandalopsis japonica): cloning, tissue expression, and effects of eyestalk ablation.
PubMed:Evidence for differential biosynthesis of juvenile hormone (and related) sesquiterpenoids in Drosophila melanogaster.
PubMed:Final steps in juvenile hormone biosynthesis in the desert locust, Schistocerca gregaria.
PubMed:Reproductive regulators in decapod crustaceans: an overview.
PubMed:JH biosynthesis by reproductive tissues and corpora allata in adult longhorned beetles, Apriona germari.
PubMed:Field trials of aggregation pheromones for the stink bugs Chlorochroa uhleri and Chlorochroa sayi (Hemiptera: Pentatomidae).
PubMed:Rapid direct analysis in real time (DART) mass spectrometric detection of juvenile hormone III and its terpene precursors.
PubMed:Morphological changes in Daphnia galeata induced by a crustacean terpenoid hormone and its analog.
PubMed:Cloning and characterization of a putative farnesoic acid O-methyltransferase gene from the brown planthopper, Nilaparvata lugens.
PubMed:Drosophila CG10527 mutants are resistant to juvenile hormone and its analog methoprene.
PubMed:Bioassays of compounds with potential juvenoid activity on Drosophila melanogaster: juvenile hormone III, bisepoxide juvenile hormone III and methyl farnesoates.
PubMed:Mass spectrometry assay as an alternative to the enzyme-linked immunosorbent assay test for biomarker quantitation in ecotoxicology: application to vitellogenin in Crustacea (Gammarus fossarum).
PubMed:Juvenile hormone and allatostatins in the German cockroach embryo.
PubMed:Activities of natural methyl farnesoids on pupariation and metamorphosis of Drosophila melanogaster.
PubMed:Evolution and functional divergence of enzymes involved in sesquiterpenoid hormone biosynthesis in crustaceans and insects.
PubMed:Methyl farnesoate synthesis in the lobster mandibular organ: the roles of HMG-CoA reductase and farnesoic acid O-methyltransferase.
PubMed:Regulation of female reproduction in mites: a unifying model for the Acari.
PubMed:Suppressed production of methyl farnesoid hormones yields developmental defects and lethality in Drosophila larvae.
PubMed:Interactions of methyl farnesoate and related compounds with a crustacean retinoid X receptor.
PubMed:The ligand-binding domains of the three RXR-USP nuclear receptor types support distinct tissue and ligand specific hormonal responses in transgenic Drosophila.
PubMed:Potential endocrine disruption of ovary synthesis in the Christmas Island red crab Gecarcoidea natalis by the insecticide pyriproxyfen.
PubMed:Molecular and functional characterization of a juvenile hormone acid methyltransferase expressed in the corpora allata of mosquitoes.
PubMed:Methyl farnesoate couples environmental changes to testicular development in the crab Carcinus maenas.
PubMed:RXR isoforms and endogenous retinoids in the fiddler crab, Uca pugilator.
PubMed:Difference in the sensitivity to chemical compounds between female and male neonates of Daphnia magna.
PubMed:Atrazine and increased male production by Daphnia: the importance of combining field and laboratory approaches.
PubMed:Chemical sensitivity of the male daphnid, Daphnia magna, induced by exposure to juvenile hormone and its analogs.
PubMed:A putative farnesoic acid O-methyltransferase (FAMeT) orthologue in Drosophila melanogaster (CG10527): relationship to juvenile hormone biosynthesis?
PubMed:Characterization of the putative farnesoic acid O-methyltransferase (LvFAMeT) cDNA from white shrimp, Litopenaeus vannamei: Evidence for its role in molting.
PubMed:Farnesoic acid O-methyl transferase (FAMeT) isoforms: conserved traits and gene expression patterns related to caste differentiation in the stingless bee, Melipona scutellaris.
PubMed:Juvenile hormone and methyl farnesoate production in cockroach embryos in relation to dorsal closure and the reproductive modes of different species of cockroaches.
PubMed:Enantioselective separation of racemic juvenile hormone III by normal-phase high-performance liquid chromatography and preparation of [(2)H(3)]juvenile hormone III as an internal standard for liquid chromatography-mass spectrometry quantification.
PubMed:Only one esterase of Drosophila melanogaster is likely to degrade juvenile hormone in vivo.
PubMed:Crustacean endocrine toxicology: a review.
PubMed:The environmental-endocrine basis of gynandromorphism (intersex) in a crustacean.
PubMed:The retinoid-X receptor ortholog, ultraspiracle, binds with nanomolar affinity to an endogenous morphogenetic ligand.
PubMed:Cloning and characterization of the retinoid X receptor from a primitive crustacean Daphnia magna.
PubMed:Isolation and expression analysis of multiple isoforms of putative farnesoic acid O-methyltransferase in several crustacean species.
PubMed:Water-flea males from the netherworld.
PubMed:Endocrine disruption in crustaceans due to pollutants: a review.
PubMed:Inhibition of ovarian development by methyl farnesoate in the tadpole shrimp, Triops longicaudatus.
PubMed:Hormonal induction of undescribed males resolves cryptic species of cladocerans.
PubMed:Characterization of vitellogenin in the shrimp Metapenaeus ensis: expression studies and hormonal regulation of MeVg1 transcription in vitro.
PubMed:Identification of methyl farnesoate from in vitro culture of the retrocerebral complex of adult females of the moth, Heliothis virescens (Lepidoptera: Noctuidae) and its conversion to juvenile hormone III.
PubMed:Expressed sequence tags from eyestalk of kuruma prawn, Marsupenaeus japonicus.
PubMed:A candidate juvenoid hormone receptor cis-element in the Daphnia magna hb2 hemoglobin gene promoter.
PubMed:Effects of eyestalk ablation on carbonic anhydrase activity in the euryhaline blue crab Callinectes sapidus: neuroendocrine control of enzyme expression.
PubMed:The effect of seawater composition and osmolality on hemolymph levels of methyl farnesoate in the green crab Carcinus maenas.
PubMed:An Arabidopsis thaliana methyltransferase capable of methylating farnesoic acid.
PubMed:The screening of chemicals for juvenoid-related endocrine activity using the water flea Daphnia magna.
PubMed:Methyl farnesoate controls adult male morphogenesis in the crayfish, Procambarus clarkii.
PubMed:Regulation of methyl farnesoate production by mandibular organs in the crayfish, Procambarus clarkii: a possible role for allatostatins.
PubMed:Covert signal disruption: anti-ecdysteroidal activity of bisphenol A involves cross talk between signaling pathways.
PubMed:Vitellogenesis in the red crab Charybdis feriatus: Hepatopancreas-specific expression and farnesoic acid stimulation of vitellogenin gene expression.
PubMed:Stress signaling: coregulation of hemoglobin and male sex determination through a terpenoid signaling pathway in a crustacean.
PubMed:Cross communication between signaling pathways: juvenoid hormones modulate ecdysteroid activity in a crustacean.
PubMed:Purification and characterization of a mandibular organ protein from the American lobster, Homarus americanus: a putative farnesoic acid O-methyltransferase.
PubMed:Interference of cadmium and copper with the endocrine control of ovarian growth, in the estuarine crab Chasmagnathus granulata.
PubMed:CYP15A1, the cytochrome P450 that catalyzes epoxidation of methyl farnesoate to juvenile hormone III in cockroach corpora allata.
PubMed:Cloning, characterization, and developmental expression of a putative farnesoic acid O-methyl transferase in the female edible crab Cancer pagurus.
PubMed:Activity of the corpora allata of adult female Aedes aegypti: effects of mating and feeding.
PubMed:1,5-Disubstituted imidazoles inhibit juvenile hormone biosynthesis by the corpora allata of the mosquito Aedes aegypti.
PubMed:3-hydroxy-3-methylglutaryl-coenzyme A reductase in the lobster mandibular organ: regulation by the eyestalk.
PubMed:Insecticidal juvenile hormone analogs stimulate the production of male offspring in the crustacean Daphnia magna.
PubMed:Responsiveness of honey bee (Apis mellifera L.) corpora allata to allatoregulatory peptides from four insect species.
PubMed:Absence of insect juvenile hormones in the American dog tick, Dermacentor variabilis (Say) (Acari:Ixodidae), and in Ornithodoros parkeri Cooley (Acari:Argasidae).
PubMed:Stimulation of JH biosynthesis by the corpora allata of adult female Aedes aegypti in vitro: effect of farnesoic acid and Aedes allatotropin.
PubMed:Methyl farnesoate and juvenile hormone production in embryos of Diploptera punctata in relation to innervation of corpora allata and their sensitivity to allatostatin.
PubMed:Juvenoid hormone methyl farnesoate is a sex determinant in the crustacean Daphnia magna.
PubMed:Function and cellular localization of farnesoic acid O-methyltransferase (FAMeT) in the shrimp, Metapenaeus ensis.
PubMed:In vivo regulation of the mandibular organ in the edible crab, Cancer pagurus.
PubMed:Effect of methyl farnesoate, alone and in combination with other hormones, on ovarian growth of the red swamp crayfish, Procambarus clarkii, during vitellogenesis.
PubMed:Evidence that ecdysteroids and methyl farnesoate control allometric growth and differentiation in a crustacean.
PubMed:Identification and synthesis of male-produced sex pheromone components of the stink bugs Chlorochroa ligata and Chlorochroa uhleri.
PubMed:Occurrence of vertebrate steroids, estradiol 17beta and progesterone in the reproducing females of the mud crab Scylla serrata.
PubMed:Low exposure concentration effects of methoprene on endocrine-regulated processes in the crustacean Daphnia magna.
PubMed:Effects of sinus gland extract on mandibular organ size and methyl farnesoate synthesis in the crawfish.
PubMed:Hemolymph levels of methyl farnesoate increase in response to osmotic stress in the green crab, Carcinus maenas.
PubMed:Clustering of mandibular organ-inhibiting hormone and moult-inhibiting hormone genes in the crab, Cancer pagurus, and implications for regulation of expression.
PubMed:Changes in protein kinase C during vitellogenesis in the crayfish Cherax quadricarinatus--possible activation by methyl farnesoate.
PubMed:Identification of methyl farnesoate in the cypris larva of the barnacle, Balanus amphitrite, and its role as a juvenile hormone.
PubMed:Terminal steps in JH biosynthesis in the honey bee (Apis mellifera L. ): developmental changes in sensitivity to JH precursor and allatotropin.
PubMed:Molecular characterization and expression of mandibular organ-inhibiting hormone, a recently discovered neuropeptide involved in the regulation of growth and reproduction in the crab Cancer pagurus.
PubMed:Involvement of adenosine cyclic-3',5'-monophosphate in the signal transduction pathway of mandibular organ-inhibiting hormone of the edible crab, Cancer pagurus.
PubMed:cDNA cloning of a mandibular organ inhibiting hormone from the spider crab Libinia emarginata.
PubMed:Neuropeptide regulation of biosynthesis of the juvenoid, methyl farnesoate, in the edible crab, Cancer pagurus.
PubMed:Purification and kinetic characterisation of juvenile hormone esterase from Drosophila melanogaster.
PubMed:Stimulation of ovarian maturation in the crayfish Procambarus clarkii by methyl farnesoate.
PubMed:Yolk protein synthesis in the riceland tadpole shrimp, Triops longicaudatus, measured by in vitro incorporation of 3H-leucine.
PubMed:Juvenile hormone acid: evidence for a hormonal function in induction of vitellogenin in larvae of Manduca sexta.
PubMed:A neurohormone regulating both methyl farnesoate synthesis and glucose metabolism in a crustacean.
PubMed:Distribution and regulation of esterases that hydrolyze methyl farnesoate in Homarus americanus and other crustaceans.
PubMed:Substrate specificity for the epoxidation of terpenoids and active site topology of house fly cytochrome P450 6A1.
PubMed:Identification and characterization of methyl farnesoate binding proteins from the crab, Cancer magister.
PubMed:Structure and significance of mandibular organ-inhibiting hormone in the crab, Cancer pagurus. Involvement in multihormonal regulation of growth and reproduction.
PubMed:A model for farnesoid feedback control in the mevalonate pathway.
PubMed:Biochemistry of proteins that bind and metabolize juvenile hormones.
PubMed:Photoaffinity labeling of methyl farnesoate epoxidase in cockroach corpora allata.
PubMed:Pathway and regulation of JHIII-Bisepoxide biosynthesis in adult Drosophila melanogaster corpus allatum.
PubMed:Characterization of a juvenile hormone binding lipophorin from the blowfly Lucilia cuprina.
PubMed:Methyl farnesoate levels in male spider crabs exhibiting active reproductive behavior.
PubMed:De novo biosynthesis of juvenile hormone III and I by the accessory glands of the male mosquito.
PubMed:Methyl farnesoate stimulates ecdysteroid secretion from crab Y-organs in vitro.
PubMed:In vivo and in vitro biosynthesis and metabolism of methyl farnesoate, juvenile hormone III, and juvenile hormone III acid in the mosquito Aedes aegypti.
PubMed:Biosynthesis and metabolism of juvenile hormone III from methyl farnesoate by exposed corpora allata of Lutzomyia anthophora.
PubMed:Regulation of methyl farnesoate in the hemolymph and mandibular organ of the lobster, Homarus americanus.
PubMed:In vitro assay for the biosynthesis and metabolism of juvenile hormone by exposed corpora allata of Aedes aegypti (Diptera: Culicidae).
PubMed:Reversible juvenile hormone inhibition of ecdysteroid and juvenile hormone synthesis by the ring gland of Drosophila melanogaster.
PubMed:Quantification of methyl farnesoate levels in hemolymph by high-performance liquid chromatography.
PubMed:Characterization of a methyl farnesoate binding protein in hemolymph from Libinia emarginata.
PubMed:Production and utilization of farnesoic acid in the juvenile hormone biosynthetic pathway by corpora allata of larval Diploptera punctata.
PubMed:Methyl farnesoate in the prawn Macrobrachium rosenbergii: synthesis by the mandibular organ in vitro, and titers in the hemolymph.
PubMed:The effect of juvenile hormone III, methyl farnesoate, and methoprene on Na/K-ATPase activity in larvae of the brine shrimp, Artemia.
PubMed:Binding proteins for methyl farnesoate in lobster tissues: detection by photoaffinity labeling.
PubMed:Juvenile hormone stimulation of ornithine decarboxylase activity during vitellogenesis in Drosophila melanogaster.
PubMed:Production of methyl farnesoate by the mandibular organs of the mud crab, Scylla serrata: validation of a radiochemical assay.
PubMed:Developmental regulation of juvenile hormone biosynthesis by the ring gland of Drosophila melanogaster.
PubMed:Evidence against the hypothesis that metacestodes of Hymenolepis diminuta inhibit corpora allata functioning in the intermediate host, Tenebrio molitor.
PubMed:Identification of a juvenile hormone-like compound in a crustacean.
PubMed:Farnesol and farnesal dehydrogenase(s) in corpora allata of the tobacco hornworm moth, Manduca sexta.
PubMed:Enzymic synthesis of juvenile hormone in locust corpora allata: evidence for a microsomal cytochrome P-450 linked methyl farnesoate epoxidase.
PubMed:Ultrastructural localization of juvenile hormone biosynthesis by insect corpora allata.
PubMed:NADPH dependent epoxidation of methyl farnesoate to juvenile hormone in the cockroach Blaberus giganteus L.
PubMed:Corpus allatum activity in vitro during ovarian maturation in the desert locust, Schistocerca gregaria.
PubMed:The influence of substrate concentrations on the rate of insect juvenile hormone biosynthesis by corpora allata of the desert locust in vitro.
 
Notes:
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