F2929
6-Fluoromevalonate
≥90% (GC), viscous liquid
Synonym(s):
Tetrahydro-4-fluoromethyl-4-hydroxy-2H-pyran-2-one, ZR 3516
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About This Item
Empirical Formula (Hill Notation):
C6H9FO3
CAS Number:
Molecular Weight:
148.13
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
Quality Level
Assay
≥90% (GC)
form
viscous liquid
color
yellow tint
solubility
DMSO: ≥3 mg/mL
storage temp.
2-8°C
SMILES string
OC1(CF)CCOC(=O)C1
InChI
1S/C6H9FO3/c7-4-6(9)1-2-10-5(8)3-6/h9H,1-4H2
InChI key
DPPMVKMESJJAJZ-UHFFFAOYSA-N
Application
6-Fluoromevalonate has been used as a mevalonate pyrophosphate decarboxylase inhibitor:
- to study the effect of mevalonate pathway inhibition on patient-derived brain tumor-initiating cells (BTICs) growth and self-renewal
- to study its effect on induction of trained immunity by β-glucan in monocytes
- to determine the effect of the mevalonate pathway (MVP) on ADP-ribosylation factor 6 (ARF6) activation
Biochem/physiol Actions
Mevalonate-pyrophosphate decarboxylase inhibitor
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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J A Cuthbert et al.
The Journal of biological chemistry, 265(30), 18568-18575 (1990-10-25)
The sterol synthesis inhibitor 6-fluoromevalonate (Fmev) was used to explore the role of mevalonate products in lymphocyte proliferation. Fmev blocks the synthesis of isopentenyl pyrophosphate and all more distal products in the sterol pathway. When cells were cultured in lipoprotein-deficient
J A Cuthbert et al.
Cancer research, 55(8), 1732-1740 (1995-04-15)
Mevalonate is the precursor of a number of different products potentially required for the growth of cells, including the prenylated oncoprotein Ras. To determine whether inhibition of mevalonate metabolism would selectively block proliferation of Ras-transformed cells, 6-fluoromevalonate (Fmev), an inhibitor
J E Carrel et al.
Experientia, 42(7), 853-854 (1986-07-15)
Biosynthesis of cantharidin in a blister beetle, Lytta polita, is effectively inhibited by 6-fluoromevalonate. Inhibition is attributed specifically to the fluorine substituent. Biochemical inhibition has not been demonstrated previously for an arthropod's defensive substance.
Ari Hashimoto et al.
The Journal of cell biology, 213(1), 81-95 (2016-04-06)
Drug resistance, metastasis, and a mesenchymal transcriptional program are central features of aggressive breast tumors. The GTPase Arf6, often overexpressed in tumors, is critical to promote epithelial-mesenchymal transition and invasiveness. The metabolic mevalonate pathway (MVP) is associated with tumor invasiveness
A Corsini et al.
Comptes rendus des seances de la Societe de biologie et de ses filiales, 191(2), 169-194 (1997-01-01)
The role of mevalonic acid (MVA) and its products (isoprenoids) in cell proliferation prompted us to investigate the effect of drugs affecting diverse enzymatic steps of the MVA pathway on rat aorta smooth muscle cell (SMC) proliferation. Competitive inhibitors of
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