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94259

Sigma-Aldrich

(±)-Mevalonic acid 5-pyrophosphate tetralithium salt

≥80% (qNMR)

Synonym(s):

(±)-MVAPP, (±)-Mevalonic acid 5-diphosphate tetralithium salt

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About This Item

Empirical Formula (Hill Notation):
C6H10Li4O10P2
CAS Number:
108869-00-7
Molecular Weight:
331.85
MDL number:
MFCD16875404
UNSPSC Code:
12352201
PubChem Substance ID:
329770318
NACRES:
NA.25

Quality Level

100

Assay

≥80% (qNMR)

form

powder

color

white

storage temp.

−20°C

SMILES string

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

InChI

1S/C6H14O10P2.4Li/c1-6(9,4-5(7)8)2-3-15-18(13,14)16-17(10,11)12;;;;/h9H,2-4H2,1H3,(H,7,8)(H,13,14)(H2,10,11,12);;;;/q;4*+1/p-4

InChI key

GFIXUUFXTAPBAD-UHFFFAOYSA-J

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Biochem/physiol Actions

Metabolite of the mevalonate pathway, which plays a key role in the biosynthesis of sterols, dolichol, heme and ubiquinone. Of interest for research in the disease areas oncology, autoimmune diseases, artherosclerosis and Alzheimer disease, as well as for inherited deficiencies of mevalonate kinase. Mevalonic acid 5-pyrophosphate was shown to elevate ubiquinone levels in rat liver tissues.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

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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Jonathan Lombard et al.
Molecular biology and evolution, 28(1), 87-99 (2010-07-24)
Isoprenoids are a very diverse family of organic compounds widespread in the three domains of life. Although they are produced from the condensation of the same precursors in all organisms (isopentenyl pyrophosphate and dimethylallyl diphosphate), the evolutionary origin of their
Luke Grundy et al.
Pain, 160(4), 793-804 (2018-12-12)
Primary afferent neurons transduce distension of the bladder wall into action potentials that are relayed into the spinal cord and brain, where autonomic reflexes necessary for maintaining continence are coordinated with pathways involved in sensation. However, the relationship between spinal
Muthusubramanian Venkateshwaran et al.
Proceedings of the National Academy of Sciences of the United States of America, 112(31), 9781-9786 (2015-07-23)
Rhizobia and arbuscular mycorrhizal fungi produce signals that are perceived by host legume receptors at the plasma membrane and trigger sustained oscillations of the nuclear and perinuclear Ca(2+) concentration (Ca(2+) spiking), which in turn leads to gene expression and downstream
D McCaskill et al.
Analytical biochemistry, 215(1), 142-149 (1993-11-15)
Procedures for the isolation and analysis of all 11 intermediates of the mevalonic acid pathway from acetyl-CoA through geranylgeranyl pyrophosphate were developed. Both acid-labile and base-labile metabolites are simultaneously extracted with good recoveries into 7 M urea at neutral pH

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