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F2929

Sigma-Aldrich

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:
2822-77-7
Molecular Weight:
148.13
MDL number:
MFCD08276919
UNSPSC Code:
51111800
PubChem Substance ID:
24724480
NACRES:
NA.77

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

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

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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.
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