CHEMISTRY OF
JUVABIONE
Introduction
• Name : Kiran Jaat
• Standard : M.Sc. Sem: 3
• Roll No:66
• Topic Name: Chemistry of Juvabione
• Department: Department of Chemistry
of KSKV Kachchh University.
Juvabione
• Juvabione, historically known as the paper
factor, is the methyl ester of todomatuic acid. It
is a natural product derived from the resin of
coniferous trees, especially Abies and Picea
species.
• It belongs to the class of terpenoids and
functions as a juvenile hormone mimic in
insects, influencing their growth and
development.
• Juvabione was initially identified for its role in
controlling insect metamorphosis and is used in Abies balsamea tree with cones, Sherburne
insect pest management National Wildlife Refuge, Minnesota
Chemical Structure
• Molecular Formula: C16H26O3
• Molecular Weight: 266.381 g/mol
• IUPAC Name: Methyl (4R)-4-[(2R)-6-
methyl-4-oxoheptan-2-yl]cyclohex-1-
ene-1-carboxylate
• Common Name: Juvabione
JUVABIONE
Chemical properties
Solubility: It is soluble in organic solvents like
ethanol, methanol, and ether, but poorly soluble in
water.
Chemical Nature: Contains an ester functional
group, which makes it susceptible to hydrolysis
under acidic or basic conditions.Has a ketone
group contributing to its reactivity in organic
transformations.
Optical Activity: Juvabione exists as a chiral
molecule, and its activity can vary between
enantiomers.
Synthesis of juvabione
• Sesquiterpenes are a class of terpenoids based upon a 15-carbon unit scaffold
synthesized from isoprene units via the mevalonate pathway In this pathway, two
molecules of acetyl-CoA undergo a condensation reaction to give acetoacetyl-CoA.
• This product then condenses with third molecule of acetyl-CoA in a stereospecific fashion
to form 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA) which then is reduced to mevalonic
acid (MVA).
• A series of ATP-dependent transformations lead to a key isoprene unit, isopentenyl
diphosphate (IPP) which can be isomerized to dimethylallyl diphosphate (DMAPP).
DMAPP ionizes to its respective allylic cation that undergoes electrophilic addition to the
double bond of IPP.
• Upon loss of a proton, geranyl diphosphate (GPP) is formed. GPP undergoes
an elimination reaction to form its corresponding allylic cation. Electrophilic addition of
another IPP unit to the GPP cation results in a tertiary carbocation intermediate that forms
a fifteen-carbon farnesyl diphosphate (FPP) upon loss of a proton.
Continue……
• Farnesyl diphosphate is the universal precursor to a wide variety of linear
and cyclized sesquiterpenes. Of particular interest to juvabione
biosynthesis (Scheme 1), dissociation of the terminal diphosphate from the
FPP precursor generates the (E,E)-farnesyl allylic cation, leading
to nerolidyl diphosphate (NPP).
• NPP is another precursor that can undergo different reaction types, but in
this case, bisabolene synthase directs a single cyclization event by
electrophilic attack of C-1 onto the double bond of C-6 to form a six-
membered ring.
• Deprotonation of the resultant tertiary cation yields (E)-α-bisabolene. Then
it converts into juvabione.
Application
• Insect Growth Regulator (IGR): Mimics juvenile hormones, disrupting insect
development and preventing metamorphosis, useful in controlling pest
populations.
• Forestry Pest Control: Naturally occurring in balsam fir, it helps protect forests by
deterring herbivorous insects.
• Eco-friendly Pesticides: Offers potential for developing biodegradable, targeted
pesticides that affect insects without harming non-target organisms or the
environment.
• Biological Research: Used to study the effects of juvenile hormones in insects and
understand sesquiterpenoid functions.
• Agriculture: Potential to manage crop-damaging pests by interfering with their life
cycle.
References
• https://en.wikipedia.org/wiki/Juvabione
• Manville, J. F.; Kriz, C. D. (1977). "Juvabione
and its analogues. IV. Isolation, identification, and occurrence of juvabione, juvabiol,
epijuvabiol from the whole wood of Abies lasiocarpa". Can. J. Chem. 55: 2547–2553. doi:
10.1139/v77-351.
• Higuchi, T. (1985). Biosynthesis and biodegradation of wood components. Academic
Press. pp. 380–429.
• Dewick, P. M (2009). "The mevalonate and methylerythritol phosphate pathways:
terpenoids and steroids". Medicinal Natural Products, 3rd Edition; Wiley: United Kingdom:
187–234. doi:10.1002/9780470742761.ch5. ISBN 9780470742761.
