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Sigma-Aldrich

Isopentenyl pyrophosphate trilithium salt

≥95.0% (TLC)

Synonym(s):

3-Methyl-3-butenyl pyrophosphate trilithium salt, IPP

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About This Item

Empirical Formula (Hill Notation):
C5H9Li3O7P2
CAS Number:
18687-43-9
Molecular Weight:
263.89
MDL number:
MFCD17215950
UNSPSC Code:
12352107
PubChem Substance ID:
329747035
NACRES:
NA.25

Assay

≥95.0% (TLC)

form

powder

impurities

≤10% water

storage temp.

−20°C

SMILES string

[Li+].[Li+].[Li+].CC(=C)CCOP([O-])(=O)OP([O-])([O-])=O

InChI

1S/C5H12O7P2.3Li/c1-5(2)3-4-11-14(9,10)12-13(6,7)8;;;/h1,3-4H2,2H3,(H,9,10)(H2,6,7,8);;;/q;3*+1/p-3

InChI key

ZJGSIAARCDPUSN-UHFFFAOYSA-K

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General description

Isopentenyl pyrophosphate trilithium salt (3-Methyl-3-butenyl pyrophosphate trilithium salt, IPP) is the lithium salt of isopentenyl pyrophosphate. It is an intermediate formed during the biosynthesis of polyisoprenoid compounds. It can be synthesized from isopentenol in a three step process. Mevalonic acid can be converted to isopentenyl pyrophosphate in an ATP-dependent process. Melavonate and isopentenyl pyrophosphate are incorporated into rubber by Hevea brasiliensis latex.

Application

Isopentenyl pyrophosphate (IPP) may be used as a substrate to study the distribution, characterization and kinetics of isopentenyl-diphosphate isomerase(s). IPP is used to study the biosynthesis of isoprenoids/terpenoids. Isopentenyl pyrophosphate may be used in rubber synthesis.

Biochem/physiol Actions

Intermediate in terpene biosynthesis

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Kazunori Okada
Bioscience, biotechnology, and biochemistry, 75(7), 1219-1225 (2011-07-09)
Plants synthesize isopentenyl diphosphate (IPP) via the mevalonate pathway and the methylerythritol phosphate (MEP) pathway. IPP is condensed to its allylic isomer, dimethylallyl diphosphate, to yield geranylgeranyl diphosphate, a common precursor for the production of cyclic diterpenoids. Studies of subcellular
The biosynthesis of rubber. Incorporation of mevalonate and isopentenyl pyrophosphate into rubber by Hevea brasiliensis-latex fractions.
B L Archer et al.
The Biochemical journal, 89(3), 565-574 (1963-12-01)
Venkatadurga Jonnalagadda et al.
Journal of the American Chemical Society, 134(15), 6568-6570 (2012-04-05)
The E. coli isopentenyl diphosphate isomerase (IDI) catalyzed reaction of isopentenyl diphosphate (IPP) in D(2)O gives a 66% yield of dimethylallyl diphosphate labeled with deuterium at the (E)-methyl group (d-DMAPP) and a 34% yield of IPP labeled with 1 mol
Nicole A Heaps et al.
Journal of the American Chemical Society, 133(47), 19017-19019 (2011-11-04)
Isopentenyl diphosphate isomerase (IDI) catalyzes the interconversion of isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP). These two molecules are the building blocks for construction of isoprenoid carbon skeletons in nature. Two structurally unrelated forms of IDI are known. A variety
C Donninger et al.
The Biochemical journal, 105(2), 545-547 (1967-11-01)
1. Isopentenol was converted into isopentenyl phosphate with phosphoryl chloride in ether containing pyridine. 2. The isopentenyl phosphate reacted in 2-methylpropan-2-ol-water with morpholine and dicyclohexylcarbodi-imide to give isopentenyl phosphoromorpholidate. 3. The isopentenyl phosphoromorpholidate, with inorganic phosphate in pyridine containing tributylamine
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