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Merck
CN

00297

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
UNSPSC Code:
12352107
PubChem Substance ID:
329747035
NACRES:
NA.25
MDL number:
MFCD17215950
Assay:
≥95.0% (TLC)
Form:
powder

Key Documents

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Product Name

Isopentenyl pyrophosphate trilithium salt, ≥95.0% (TLC)

SMILES string

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

InChI key

ZJGSIAARCDPUSN-UHFFFAOYSA-K

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

assay

≥95.0% (TLC)

form

powder

impurities

≤10% water

storage temp.

−20°C

Quality Level

100

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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

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM2396
BCCL2212
BCCC8707
BCBT3853
BCBC1383V

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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
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)
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
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