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91356

Sigma-Aldrich

trans,trans-Farnesyl monophosphate ammonium salt

≥95.0% (TLC)

Synonym(s):

(E,E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-yl phosphate ammonium salt, 3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol dihydrogen phosphate ammonium salt, Farnesyl phosphate ammonium salt

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About This Item

Empirical Formula (Hill Notation):
C15H27O4P · xNH3
CAS Number:
15416-91-8
Molecular Weight:
302.35 (free acid basis)
MDL number:
MFCD25973942
UNSPSC Code:
12352200
NACRES:
NA.25
Assay:
≥95.0% (TLC)
form:
powder

Quality Level

100

Assay

≥95.0% (TLC)

form

powder

storage temp.

−20°C

SMILES string

[P](=O)(OC\C=C(/CC\C=C(/CCC=C(C)C)\C)\C)(O)O

InChI

1S/C15H27O4P/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-19-20(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H2,16,17,18)/b14-9-,15-11-

InChI key

ALEWCKXBHSDCCT-FBXUGWQNSA-N

Application

Trans, trans-Farnesyl monophosphate (FMP) may be used in studies of potential endogenous modulators of nuclear lysophosphatidic acid (LPA) receptors and in the active site analysis of protein farnesyltransferase(s). Trans,trans-Farnesyl monophosphate may also be used to identify and characterize farnesyl monophosphate kinases.

Biochem/physiol Actions

Farnesyl monophosphate is a metabolite in terpenoid backbone biosynthesis. It was shown to activate PPARalpha and PPARbeta/delta reporter gene expression, indicating new potential roles for the oligoprenyl phosphates as potential endogenous modulators of LPA targets.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

91356-VAR:
91356-10MG:
91356-BULK:
91356-50MG:

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Certificates of Analysis (COA)

Lot/Batch Number
BCBD1906V
BCBD1906

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Karoly Liliom et al.
Biochimica et biophysica acta, 1761(12), 1506-1514 (2006-11-10)
Oligoprenyl phosphates are key metabolic intermediates for the biosynthesis of steroids, the side chain of ubiquinones, and dolichols and the posttranslational isoprenylation of proteins. Farnesyl phosphates are isoprenoid phosphates that resemble polyunsaturated fatty alcohol phosphates, which we have recently shown
L Thai et al.
Proceedings of the National Academy of Sciences of the United States of America, 96(23), 13080-13085 (1999-11-11)
The ability of Nicotiana tabacum cell cultures to utilize farnesol (F-OH) for sterol and sesquiterpene biosynthesis was investigated. [(3)H]F-OH was readily incorporated into sterols by rapidly growing cell cultures. However, the incorporation rate into sterols was reduced by greater than
M Bentinger et al.
Archives of biochemistry and biophysics, 353(2), 191-198 (1998-06-02)
As farnesol may serve as a nonsterol endogenous regulator of the mevalonate pathway, the possibility that a kinase specific for its phosphorylation is present in the rat liver was investigated. In the 10,000 g supernatant of rat liver, farnesyl monophosphate
M J Saderholm et al.
Biochemistry, 39(40), 12398-12405 (2000-10-04)
Protein farnesyltransferase catalyzes the posttranslational farnesylation of several proteins involved in signal transduction, including Ras, and is a target enzyme for antitumor therapies. Efficient product formation catalyzed by protein farnesyltransferase requires an enzyme-bound zinc cation and high concentrations of magnesium
Michelle K Clark et al.
Journal of medicinal chemistry, 50(14), 3274-3282 (2007-06-09)
Certain farnesyl diphosphate (FPP) analogs are potent inhibitors of the potential anticancer drug target protein farnesyltransferase (FTase), but these compounds are not suitable as drug candidates. Thus, phosphoramidate prodrug derivatives of the monophosphate precursors of FPP-based FTase inhibitors have been
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