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68519

Sigma-Aldrich

(R)-(−)-Mevalonolactone

≥90.0% (GC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C6H10O3
CAS Number:
Molecular Weight:
130.14
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:

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 Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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
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
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)
Nelson L Brock et al.
Chembiochem : a European journal of chemical biology, 12(17), 2667-2676 (2011-10-13)
The fungus Fusarium fujikuroi IMI58289 emits a complex pattern of volatile terpenoids including two major compounds, the sesquiterpene alcohol α-acorenol and the diterpene ent-kaurene. ent-Kaurene is the precursor for the phytohormone gibberellic acid (GA(3)) and is produced from geranylgeranyl diphosphate
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

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