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J2000

Sigma-Aldrich

Juvenile hormone III

≥65%, liquid, non-sterile

Synonym(s):

Methyl farnesoate, 10,11-epoxide, C16-Juvenile Hormone, JH-III, Manduca hormone, trans,trans-10,11-Epoxy-3,7,11-trimethyl-2,6-dodecadienic acid methyl ester

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About This Item

Empirical Formula (Hill Notation):
C16H26O3
CAS Number:
24198-95-6
Molecular Weight:
266.38
Beilstein/REAXYS Number:
1316317
EC Number:
246-072-9
MDL number:
MFCD00135990
UNSPSC Code:
51111800
PubChem Substance ID:
24896191
NACRES:
NA.32

biological source

synthetic (organic)

Quality Level

200

sterility

non-sterile

form

liquid

concentration

≥65%

technique(s)

activity assay: suitable

shipped in

ambient

storage temp.

−20°C

SMILES string

COC(=O)\C=C(/C)CC\C=C(/C)CC[C@H]1OC1(C)C

InChI

1S/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+

InChI key

QVJMXSGZTCGLHZ-ZPLWXOMKSA-N

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General description

Research Area: Cell Signaling

Juvenile hormone III (JH III) is the most prevalent juvenile hormone (JH) found in insects.

Application

Juvenile hormone III has been used to:
  • study the effect of juvenile hormone on mictic (sexual) female production of the rotifer Brachionus plicatilis Muller
  • study the effect of juvenile hormone on head GB19811 (putative Takeout/juvenile hormone binding protein) mRNA levels in adult honeybees
  • study the effect of juvenile hormone on gonadotropic and physiological functions in bumblebee Bombus terrestris

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.Juvenile hormones(JHs) are a group of acyclic sesquiterpenoids, and in some insect lineages, the farnesol backbone of these compounds undergoes chemical modification to produce a homologous series of hormones. JH is essential for insect development and reproduction in every aspect. It plays a key role in metamorphosis and caste determination in social insects. It modulates behavior, polyphenism, larval and adult diapause, and ovarian development. The sesquiterpenoid backbone of juvenile hormone III (JH III) is biosynthesized through the classical mevalonate (MVA) pathway in cockroaches.
Controls the larval metamorphosis of insects, including the retention of juvenile characteristics.

hcodes

H413

Hazard Classifications

Aquatic Chronic 4

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Linquan Ge et al.
Frontiers in physiology, 11, 579233-579233 (2020-10-13)
The mirid bug, Cyrtorhinus lividipennis Reuter, is an important predator of rice planthoppers in Asia. In a previous study, C. lividipennis fed on gramineous weeds with brown planthopper (BPH) eggs had reduced development compared to those fed on rice with
Cheolho Sim et al.
Insect molecular biology, 22(1), 1-11 (2012-11-06)
Juvenile hormone (JH) controls diverse physiological and developmental events including diapause and nutrient metabolism. The focal point of endocrine regulation in adult reproductive diapause is initiated by a halt of JH synthesis. In diapausing females of the mosquito Culex pipiens
Tzachi Hagai et al.
Insect biochemistry and molecular biology, 37(7), 689-701 (2007-06-07)
We identified and characterized eight genes encoding putative Takeout/juvenile hormone binding proteins (To/JHBP) in the honeybee genome. Phylogenetic analyses revealed nine distinct lineages within this gene family, including those containing Takeout (To) and JHBP for which there are no honeybee
Gallardo et al.
Journal of experimental marine biology and ecology, 252(1), 97-107 (2000-08-30)
Juvenile hormone (JH) and serotonin (5-HT) were previously shown to enhance mictic (sexual) female production of the rotifer Brachionus plicatilis in batch cultures. To explore the basis of these effects, experiments were conducted on isolated individuals. JH treatment of maternal
Jesus Lozano et al.
Scientific reports, 1, 163-163 (2012-02-23)
Insect metamorphosis is regulated by ecdysteroids, which induce molts, and juvenile hormone (JH), which inhibits metamorphic changes. The molecular action of ecdysteroids has been thoroughly studied, but that of JH is poorly understood, with data currently only being available for
View All Related Papers

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