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Usage

Uses

Used in Entomology Research:
JUVENILE HORMONE III is used as a research tool for studying the effects of juvenile hormone on the development and reproduction of insects. It helps researchers understand the underlying mechanisms and pathways involved in insect growth and maturation.
Used in Rotifer Studies:
In the study of the rotifer Brachionus plicatilis Muller, JUVENILE HORMONE III is used as a stimulant to investigate the effect of juvenile hormone on mictic (sexual) female production. This research contributes to the understanding of the role of juvenile hormone in the reproductive success of this species.
Used in Honeybee Research:
JUVENILE HORMONE III is used as a modulator in the study of head GB19811 (putative Takeout/juvenile hormone binding protein) mRNA levels in adult honeybees. This application aids in understanding the influence of juvenile hormone on gene expression and its implications on honeybee development and behavior.
Used in Bumblebee Research:
In the study of the bumblebee Bombus terrestris, JUVENILE HORMONE III is used as a regulator to examine the effect of juvenile hormone on gonadotropic and physiological functions. This research provides insights into the hormonal control of reproductive processes in bumblebees and their ecological implications.

Biochem/physiol Actions

JHBPs (JH-binding proteins) protect JH (juvenile hormone) from JH esterase- and epoxide hydrolase-mediated degradation. They also help in delivering JH to target tissues.

InChI:InChI=1/C16H26O3/c1-12(9-10-14-16(3,4)19-14)7-6-8-13(2)11-15(17)18-5/h7,11,14H,6,8-10H2,1-5H3/b12-7+,13-11+

Upstream product

• 3675-00-1 methyl (E,E)-farnesoate 
• 100991-76-2 methyl 3,7-dimethyl-10,10-dimethoxy-2ξ,6E-decadienoate 
• 128266-55-7 t-butyl 3,7,11-trimethyl-dodeca-2(E,Z),6E,10-trienoate 
• 10147-50-9 (2E,6E)-10,11-epoxy-3,7,11-trimethyldodeca-2,6-dienoic acid 
• 74-88-4 methyl iodide 
• 3796-70-1 trans geranyl acetone 
• 100991-77-3 methyl 3,7-dimethyl-10-oxo-2ξ,6E-decadienoate 
• 94887-47-5 (E)-1,1-dimethoxy-8-oxo-4-methyl-4-nonene 
• 56194-27-5 methyl (6E)-farnesoate 

Downstream Products

• 84072-15-1 C₁₆H₂₆O₃ 
• 10147-50-9 (2E,6E)-10,11-epoxy-3,7,11-trimethyldodeca-2,6-dienoic acid 
• 25506-84-7 Methyl (2E)-6,7,10,11-diepoxy-3,7,11-trimethyldodec-2-enoate 

Relevant academic research and scientific papers

First preparation of single-enantiomer juvenile hormone III acid and (R)-juvenile hormone III-d3

The (R)- and (S)-enantiomers of juvenile hormone (JH) III acid [(R)-2 and (S)-2] were prepared by the hydrolysis of (R)- and (S)-JH III [(R)-1 and (S)-1], respectively. Each enantiomer of 2 was purified by preparative reversed-phase high performance liquid chromatography in a single operation. (RS)-2 was methylated with CH3I and K2CO3 in MeCN, yielding (RS)-1. (R)-JH III-d3 [(R)-3], a single-enantiomer internal standard for quantification, was prepared from (R)-2 with CD3I and K2CO3 in MeCN.

Substrate specificity for the epoxidation of terpenoids and active site topology of house fly cytochrome P450 6A1

Heterologous expression in Escherichia coli, purification, and reconstitution of house fly P450 6A1 and NADPH-cytochrome P450 reductase were used to study the metabolism of terpenoids. In addition to the epoxidation of cyclodiene insecticides demonstrated previously [Andersen et al. (1994) Biochemistry 33, 2171-2177], this cytochrome P450 was shown to epoxidize a variety of terpenoids such as farnesyl, geranyl, and neryl methyl esters, juvenile hormones I and III, and farnesal but not farnesol or farnesoic acid. P450 6A1 reconstituted with NADPH-cytochrome P450 reductase and phosphatidylcholine did not metabolize α-pinene, limonene, or the insect growth regulators hydroprene and methoprene. The four geometric isomers of methyl farnesoate were metabolized predominantly to the 10,11-epoxides, but also to the 6,7-epoxides and to the diepoxides. The 10,11-epoxide of methyl (2E,6E)-farnesoate was produced in a 3:1 ratio of the (10S) and (10R) enantiomers. Monoepoxides of methyl farnesoate were metabolized efficiently to the diepoxides. Methyl farnesoate epoxidation was strongly inhibited by a bulky substituted imidazole. The active site topology of P450 6A1 was studied by the reaction of the enzyme with phenyldiazene to form a phenyl-iron complex. Ferricyanide-induced in situ migration of the phenyl group showed formation of the N-phenylprotoporphyrinporphyrin IX adducts in a 17:25:33:24 ratio of the N(B):N(A):N(C):N(D) isomers. These experiments suggest that metabolism of xenobiotics by this P450, constitutively overexpressed in insecticide-resistant strains of the house fly, is not severely limited by stereochemically constrained access to the active site.

Epoxidation of Carbon-Carbon Double Bonds in Terpenes by Linoleic Acid Hydroperoxides

Epoxidation of C=C double bonds in terpenes is achieved by reaction with linoleic acid hydroperoxides (LOOH) exemplified with caryophyllene (3), methyl farnesoate (5) and squalene (8).Linoleic acid (9S)-hydroperoxide was obtained by reaction of linoleic acid (1) with lipoxygenase present in tomato homogenisate.When 18O2-labeled (9S)-LOOH (2) was used 18O was found in the terpene epoxide.While 3 is converted under physiological conditions regioselectivity in high yield into its 4,5-epoxide 4, the yield of epoxidized products from long-chain molecules, e.g. squalene (8), decreases strongly and no regioselectivity was observed. - Key Words: Terpenes/ Epoxides/ Linoleic acid derivatives/ Hydroperoxides/ Labeled compounds, 18O2

Regio- and Chemoselective Epoxidation of Fluorinated Monoterpenes and Sesquiterpenes by Dioxiranes

A comparative study on chemoselectivity of dimethyldioxirane (DMD) and methyl(trifluoromethyl)dioxirane (TFMD) in the epoxidation of trisubstituted C=C bonds presenting different activation in fluorinated monoterpene and sesquiterpene derivatives has been carried out.With respect to DMD, epoxidations performed with TFMD were faster under milder conditions, although high conversion yields were obtained with both reagents.In ease of epoxidation of unsaturated moieties the trend observed was: (CH3)(R1)C=CH(R2) ca. (CH3)(R1)C=CH(CH2OR) ca. (CH3)(R1)C=CF(R2) >> (CH3)(R1)C=CH(COOR) > (CF3)(R1)C=CH(R2).Results reported herein present the first example of direct epoxidation of a double bond bearing a CF3 substituent by non-biochemical means.Key Words: Epoxidation.Dimethyldioxirane; Methyl(trifluoromethyl)dioxirane.Chemoselectivity.Regioselectivity.Monoterpenes.Sesquiterpenes.

A Convenient Method for the Preparation of (+/-)Juvenile Hormone III

Following a different approach methyl (2E,6E)-farnesoate (4) was prepared in three steps from trans-geranylacetone (1).Compound 4 was regioselectively epoxidized to (+/-)juvenile hormone III.

ON THE COHERENCE OF INCORPORATION OF THE FLUOROVINYL MOIETY INTO BIOACTIVE ORGANIC COMPOUNDS. SYNTHESIS OF AN INSECT JUVENILE HORMONE III FLUORINATED ANALOG.

An insect juvenile hormone fluoroanalog, methyl 10-fluoro-10,11-epoxyfarnesoate (9), has been prepared, using tandem Claisen-Cope rearrangements on fluorovinyl intermediate 1 as a crucial step.Along this synthesis chemical and spectral data have been obtained that might question some applications of fluorovinyl derivatives in the design of bioactive organic compounds.

OZONOLYSIS OF ALKENES AND REACTIONS OF POLYFUNCTIONAL COMPOUNDS. XXVII. A CONVENIENT STEREOSPECIFIC SYNTHESIS OF RACEMIC INSECT JUVENILE HORMONE YUG-III

A new method was developed for the stereospecific synthesis of the racemic insect juvenile hormone YUG-III, based on the selective ozonolysis of 1,5,9-trimethyl-1E,5E,9E-cyclododecatriene to 4-methyl-1,1-dimethoxy-2-oxo-4E-nonene.Subsequent coupling with isopropylidenetriphenylphosphorane and oxidation at the terminal double bond leads to methyl 3,7,11-trimethyl-10,11-epoxy-2E,6E-dodecadienoate with a total yield of 12percent.