Skip to Content
Merck
All Photos(1)

Key Documents

More Documents

00297

Sigma-Aldrich

Isopentenyl pyrophosphate trilithium salt

≥95.0% (TLC)

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Looking for similar products? Visit Product Comparison Guide

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Nagendra K Sharma et al.
Biochemistry, 49(29), 6228-6233 (2010-06-22)
Isopentenyl diphosphate isomerase (IDI) catalyzes the interconversion of isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP), the basic five-carbon building blocks of isoprenoid molecules. Two structurally unrelated classes of IDIs are known. Type I IPP isomerase (IDI-1) utilizes a divalent metal
New aspects of rubber biosynthesis.
Archer B L and Audrey B G
Botanical Journal of the Linnean Society, 94, 181-196 (1987)
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
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service