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68519

Sigma-Aldrich

(R)-(−)-Mevalonolactone

≥90.0% (GC)

Sinónimos:

(R)-3-Hydroxy-3-methyl-δ-valerolactone, (R)-Mevalolactone, D-Mevalonic acid lactone

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About This Item

Fórmula empírica (notación de Hill):
C6H10O3
Número de CAS:
19115-49-2
Peso molecular:
130.14
MDL number:
MFCD01074894
UNSPSC Code:
12352204
PubChem Substance ID:
329760949

assay

≥90.0% (GC)

form

liquid

optical activity

[α]/D -20±3°, c = 1 in ethanol

storage temp.

2-8°C

SMILES string

C[C@@]1(O)CCOC(=O)C1

InChI

1S/C6H10O3/c1-6(8)2-3-9-5(7)4-6/h8H,2-4H2,1H3/t6-/m1/s1

InChI key

JYVXNLLUYHCIIH-ZCFIWIBFSA-N

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Biochem/physiol Actions

Classical enantiomerically pure metabolite in biosynthetic pathways leading to sterols, terpenes, carotenoids, and other natural products.

Packaging

Amber colored round bottle

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
BCCB5931
BCBZ9564
BCBV7730
BCBV1725
BCBP9824V

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Akira Honda et al.
Journal of lipid research, 48(5), 1212-1220 (2007-02-03)
We have developed a new sensitive and specific nonradioisotope assay method to measure the activity of HMG-CoA reductase, the rate-controlling enzyme in the cholesterol biosynthetic pathway. This method was based upon a stable isotope dilution technique by liquid chromatography-tandem mass
Jenna Waldron et al.
Annals of clinical biochemistry, 48(Pt 3), 223-232 (2011-03-01)
Mevalonic acid (MVA) is synthesized at an early and rate-limiting step in the biosynthesis of cholesterol by the enzyme hydroxymethylglutaryl coenzyme A (HMG-CoA) reductase, and is a useful measure of statin efficacy or treatment. A liquid chromatography-tandem mass spectrometry (LC-MS/MS)
Shikui Zhao et al.
Bioorganic & medicinal chemistry, 17(23), 7915-7923 (2009-11-03)
A novel series of 2-cyclopropyl-4-thiophenyl quinoline-based mevalonolactones were synthesized from the substituted anilines by several reactions. Among them, (4R,6S)-6-[(E)-2-(2-cyclopropyl-6-fluoro-4-(4-fluoro-thiophenyl)-quinoline-3-yl)-ethenyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one (1d), (4R,6S)-6-[(E)-2-(2-cyclopropyl-6-fluoro-4-(3-methoxy-thiophenyl)-quinoline-3-yl)-ethenyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one (1f) and (4R,6S)-6-[(E)-2-(2-cyclopropyl-6-fluoro-4,7-di(3-methoxy-thiophenyl)-quinoline-3-yl)-ethenyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one (1q) showed potent HMG-CoA reductase inhibitory activity comparable with pitavastatin.
Jessica Fuhrmeister et al.
Toxicology letters, 215(3), 219-227 (2012-10-25)
Statins are the most widely used drugs for the treatment of hypercholesterolemia. In spite of their overall favorable safety profile, they do possess serious myotoxic potential, whose molecular origin has remained equivocal. Here, we demonstrate in cultivated myoblasts and skeletal
Ya Sh Schwartz et al.
Bulletin of experimental biology and medicine, 148(3), 406-409 (2010-04-17)
We studied the effects of cholesterol, its oxidized derivatives mevalonate, and nuclear receptor agonists LXR, RXR, and FXR on the production of transforming growth factor-beta1 (TGF- beta1) by macrophages. After recruiting of macrophage monocytes into the focus of inflammation, the
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