10485-70-8 Usage
Description
(E,E)-METHYL FARNESOATE, also known as methyl farnesoate, is a member of the juvenile hormone family of compounds. It is the methyl ester of farnesoic acid and is found in several species of crustaceans. This bioactive compound plays a crucial role in the growth, development, and reproduction of these organisms.
Uses
Used in Pharmaceutical Industry:
(E,E)-METHYL FARNESOATE is used as a pharmaceutical agent for its potential applications in regulating the growth and development of crustaceans. It can be employed in the development of drugs targeting crustacean-related diseases or for controlling their population in specific environments.
Used in Research and Development:
(E,E)-METHYL FARNESOATE is used as a research compound for studying the hormonal regulation and signaling pathways in crustaceans. This can help scientists understand the underlying mechanisms of their growth, development, and reproduction, leading to potential breakthroughs in crustacean biology and ecology.
Used in Aquaculture:
(E,E)-METHYL FARNESOATE is used as a growth regulator in the aquaculture industry, particularly for crustacean farming. By controlling the levels of this compound, farmers can potentially enhance the growth and development of crustaceans, leading to increased productivity and better yields.
Used in Pheromone Production:
(E,E)-METHYL FARNESOATE is used as a component in the synthesis of pheromones for crustaceans. These pheromones can be employed in various applications, such as attracting or repelling specific crustacean species, which can be beneficial for pest control or conservation efforts.
Used in Chemical Synthesis:
(E,E)-METHYL FARNESOATE can be used as a starting material or intermediate in the synthesis of other bioactive compounds, such as insect hormones or pharmaceuticals. Its unique structure and properties make it a valuable building block for the development of new molecules with potential applications in various industries.
Discovery
In 1987, Laufer and his colleagues first identified methyl farnesoate (MF) from the hemolymph of the spider crab Libinia emarginata as a juvenile hormone (JH)-like factor produced by the mandibular organs (MOs). Since then, MF has been found in more than 35 crustacean species.MF is also found in several insect species, and a species of mite.
Properties
MF is lipophilic, and highly soluble in hexane and ethanol.
Biological functions
MF has multiple physiological functions, including the regulation of metabolism, molting, reproduction, behavior, and morphogenesis in crustaceans.It stimulates general protein synthesis and ecdysteroid secretion by the Y-organ, and influences the molting cycle.MF plays a key role in the regulation of crustacean reproduction; it enhances egg production in females, and affects the reproductive morphology and behavior in males.The expression of the vitellogenin (Vg) gene is induced by MF in the hepatopancreas, although FA is more potent than MF for this activity.MF has either a stimulatory or an inhibitory role in metamorphosis, depending on the species and developmental stages.MF functions as a sex determinant and induces the production of male offspring in daphnids and other cladoceran species,and is also involved in predator-induced polyphenisms in Daphnia.
Synthesis
MF is synthesized by and secreted from the MOs of crustaceans. Like insect JH, MF is synthesized from acetyl-CoA through the mevalonate pathway and the MF-specific pathway.The farnesoic acid O-methyltransferase (FAMeT) gene has been considered as encoding the enzyme that catalyzes FA to MF in crustaceans.In contrast, in insects MF is synthesized from FA by an enzyme encoded in JHAMT, which belongs to a gene family distinct from FAMeT.Recently, JHAMT homologs were also found in the waterflea Daphnia pulex and a species of mite.Therefore, the relevance of FAMeT and JHAMT in MF synthesis in crustaceans and other arthropods needs to be reassessed.
Synthesis Reference(s)
Journal of the American Chemical Society, 101, p. 4401, 1979 DOI: 10.1021/ja00509a073
Check Digit Verification of cas no
The CAS Registry Mumber 10485-70-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,0,4,8 and 5 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 10485-70:
(7*1)+(6*0)+(5*4)+(4*8)+(3*5)+(2*7)+(1*0)=88
88 % 10 = 8
So 10485-70-8 is a valid CAS Registry Number.
InChI:InChI=1/C16H26O2/c1-13(2)8-6-9-14(3)10-7-11-15(4)12-16(17)18-5/h8,10,12H,6-7,9,11H2,1-5H3/b14-10+,15-12+
10485-70-8Relevant articles and documents
Niaviolides, new macrocyclic sesquiterpenes secreted by males of the African butterfly Amauris niavius
Stritzke, Katja,Schulz, Stefan,Boppre, Michael
, p. 1337 - 1342 (2003)
The abdominal androconial organs ("hairpencils") of the African butterfly Amauris niavius (Danainae) emit a complex scent bouquet consisting of previously described aromatic compounds, terpenoids, fatty acids, and hydrocarbons. This work reports the identification of two major sesquiterpenes, each possessing a unique 13-membered macrolide ring, originating from an α,ω-oxidation pattern of the sesquiterpene backbone. To the best of our knowledge, sesquiterpene macrolides have not been found before in nature. The structure elucidation of the two compounds, which we propose to call niaviolide (3) and epoxyniaviolide (4), by NMR and GC/MS experiments is presented, together with their subsequent synthesis. Finally, the absolute configuration of natural 4 was determined to be (S,S) by stereoselective synthesis and chiral gas chromatography. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
A NOVEL METHOD FOR THE TERPENE SYNTHESIS BY THE RING-OPENING REACTION OF β-METHYL-β-PROPIOLACTONE
Fujisawa, Tamotsu,Sato, Toshio,Kawara, Tatsuo,Noda, Atsunari,Obinata,Toshiyuki
, p. 2553 - 2554 (1980)
A new route for the terpene synthesis is investigated, which undergoes via terpene carboxylic acids as key intermediates obtained by the regiospecific ring opening of β-methyl-β-propiolactone with cuprate or with a Grignard reagent in the presence of a copper catalyst.
