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50838

Sigma-Aldrich

(R)-Mevalonic acid lithium salt

≥93.0% (qNMR)

Synonym(s):

Lithium (R)-3,5-dihydroxy-3-methylpentanoate, Lithium (R)-3,5-dihydroxy-3-methylvalerate, R-MVA-Li

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About This Item

Empirical Formula (Hill Notation):
C6H11LiO4
CAS Number:
1255502-07-8
Molecular Weight:
154.09
MDL number:
MFCD18632545
UNSPSC Code:
12352106
PubChem Substance ID:
329757638
NACRES:
NA.25

Assay

≥93.0% (qNMR)

optical activity

[α]/D -26±3°, c = 0.1 in 0.1 M HCl (16 h)

storage temp.

2-8°C

SMILES string

[Li+].C[C@@](O)(CCO)CC([O-])=O

InChI

1S/C6H12O4.Li/c1-6(10,2-3-7)4-5(8)9;/h7,10H,2-4H2,1H3,(H,8,9);/q;+1/p-1/t6-;/m1./s1

InChI key

PVWNXFFXFNEHDZ-FYZOBXCZSA-M

Application

Mevalonic acid may be used as a reference material in assays for the separation or detection of mevalonic acid. Mevalonic acid is a precursor of isopentenyl pyrophosphate (IPP) and the mevalonate pathway which leads to isoprenoid biosynthesis. Mevalonic acid may be used as a substrate to identify and characterize mevalonate kinase(s).

Biochem/physiol Actions

Mevalonic acid, is an intermediate in the mevalonate pathway, producing terpenes and steroids. This function provides treatment options metabolic disorders , R-mevalonate accumulates in patients with the autosomal recessively inherited mevalonic acidurias, an inborn error of cholesterol and nonsterol isoprene biosynthesis.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2

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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Irina Buhaescu et al.
Clinical biochemistry, 40(9-10), 575-584 (2007-05-01)
Mevalonate pathway is an important metabolic pathway which plays a key role in multiple cellular processes by synthesizing sterol isoprenoids, such as cholesterol, and non-sterol isoprenoids, such as dolichol, heme-A, isopentenyl tRNA and ubiquinone. While extensively studied in regard with
S M Houten et al.
Cellular and molecular life sciences : CMLS, 60(6), 1118-1134 (2003-07-16)
Mevalonate kinase (MK) is an essential enzyme in the isoprenoid biosynthesis pathway which produces numerous biomolecules (isoprenoids) involved in a variety of cellular processes. The indispensability of MK and isoprenoid biosynthesis for human health is demonstrated by the identification of
Enantiomerically pure phosphonate analogues of cis- and trans-4-hydroxyprolines.
Cornforth, R. H., et al.
Tetrahedron, 18, 1351-1354 (1962)
A Scoppola et al.
Kidney international, 51(3), 908-912 (1997-03-01)
Mevalonic acid (mevalonate or MVA), is an obligate precursor in the biosynthetic pathway of cholesterol. It is partially metabolized by the kidneys and its plasma concentrations are an index of endogenous cholesterol synthesis. The aim of the present study was
Dorothea Haas et al.
Orphanet journal of rare diseases, 1, 13-13 (2006-05-26)
Mevalonic aciduria (MVA) and hyperimmunoglobulinemia D syndrome (HIDS) represent the two ends of a clinical spectrum of disease caused by deficiency of mevalonate kinase (MVK), the first committed enzyme of cholesterol biosynthesis. At least 30 patients with MVA and 180
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