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Merck
CN

F2929

Sigma-Aldrich

6-Fluoromevalonate

≥90% (GC), Mevalonate-pyrophosphate decarboxylase inhibitor, 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:
2822-77-7
Molecular Weight:
148.13
MDL number:
MFCD08276919
UNSPSC Code:
51111800
PubChem Substance ID:
24724480
NACRES:
NA.77

Key Documents

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Product Name

6-Fluoromevalonate, ≥90% (GC), viscous liquid

Quality Level

100

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

Related Categories

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000356977
0000356976
0000356977
0000356976
0000163798

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A Iwama et al.
Clinical and experimental pharmacology & physiology. Supplement, 22(1), S318-S320 (1995-01-01)
1. Phosphatidylinositol 3-kinase (PI3K) appears to have a crucial role in cellular proliferation induced by platelet-derived growth factor (PDGF). However, the mode of activation of the enzyme has been unclear so far. In the present study, we investigated the effects
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.
J A Cuthbert et al.
The Journal of biological chemistry, 266(27), 17966-17971 (1991-09-25)
The role of mevalonate and its products in the regulation of cellular proliferation was examined using 6-fluoromevalonate (Fmev), a compound that blocks the conversion of mevalonate pyrophosphate to isopentenyl pyrophosphate. Fmev suppressed DNA synthesis by a variety of transformed and
M Sawamura et al.
Clinical and experimental pharmacology & physiology, 20(7-8), 509-514 (1993-07-01)
1. Recent investigations revealed that isoprenoid compounds serve as key substances for cellular proliferation through post-translational modification. Previously we reported that tissues of spontaneously hypertensive rats (SHR) had a lower activity of isoprenoid biosynthesis when compared with the normotensive control
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
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