All Photos(1)
Synonym(s):
(R)-3-Hydroxy-3-methyl-δ-valerolactone, (R)-Mevalolactone, D-Mevalonic acid lactone
Empirical Formula (Hill Notation):
C6H10O3
CAS Number:
Molecular Weight:
130.14
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
Recommended Products
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
WGK
WGK 3
Flash Point(F)
closed cup
Flash Point(C)
closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Synthesis and HMG-CoA reductase inhibition of 2-cyclopropyl-4-thiophenyl-quinoline mevalonolactones.
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.
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)
Monica P Polo et al.
Biochemistry and cell biology = Biochimie et biologie cellulaire, 84(1), 102-111 (2006-02-08)
Monoterpenes have multiple pharmacological effects on the metabolism of mevalonate. Geraniol, a dietary monoterpene, has in vitro and in vivo anti-tumor activity against several cell lines. We have studied the effects of geraniol on growth, fatty-acid metabolism, and mevalonate metabolism
Pierrette Bouvier-Navé et al.
Plant physiology, 152(1), 107-119 (2009-11-20)
Genes encoding sterol ester-forming enzymes were recently identified in the Arabidopsis (Arabidopsis thaliana) genome. One belongs to a family of six members presenting homologies with the mammalian Lecithin Cholesterol Acyltransferases. The other one belongs to the superfamily of Membrane-Bound O-Acyltransferases.
Tomoyuki Nishimoto et al.
Toxicology and applied pharmacology, 223(1), 39-45 (2007-06-30)
High-dose statin treatment has been recommended as a primary strategy for aggressive reduction of LDL cholesterol levels and protection against coronary artery disease. The effectiveness of high-dose statins may be limited by their potential for myotoxic side effects. There is
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