F6892

Sigma-Aldrich

Farnesyl pyrophosphate ammonium salt

methanol:ammonia solution, ≥95% (TLC)

Synonym(s):
3,7,11-Trimethyl-2,6,10-dodecatrien-1-yl pyrophosphate ammonium salt, FPP
Empirical Formula (Hill Notation):
C15H37N3O7P2
CAS Number:
Molecular Weight:
433.42
MDL number:
PubChem Substance ID:
NACRES:
NA.83
Pricing and availability is not currently available.

Quality Level

assay

≥95% (TLC)

form

methanol:ammonia solution

packaging

vial of 200 μg

storage temp.

−20°C

SMILES string

C\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O

InChI

1S/C15H28O7P2/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-21-24(19,20)22-23(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H,19,20)(H2,16,17,18)/b14-9+,15-11+

InChI key

VWFJDQUYCIWHTN-YFVJMOTDSA-N

Gene Information

rat ... Fnta(25318)

General description

Farnesyl pyrophosphate is a 15-carbon isoprenoid synthesized from geranyl pyrophosphate (GPP) by the action of enzyme farnesyl pyrophosphate synthase (FPPS).

Application

Farnesyl pyrophosphate ammonium salt has been used:
  • as a prenylation agonist in human osteogenic sarcoma cells in collagen-based cell invasion assays
  • in the prenylation of the hepatocyte growth factor (HGF) in human umbilical vein endothelial cells (HUVECs)
  • as a substrate in prenyltransferases assay in diatom Haslea ostrearia

Packaging

5 vials in poly bottle
1 vial in poly bottle

Biochem/physiol Actions

Farnesyl pyrophosphate (FPP) is the precursor for the biosynthesis of cholesterol, ubiquinone and dolicol. It is part of the intracellular mevalonate pathway. FPP is essential for cell survival and is used for prenylation of several low molecular mass G proteins, including Ras. Inhibition of prenylation results in loss of oncogenic potential of Ras proteins. Inhibition of prenylation may serve as therapeutic potential for management of synaptic plasticity and Alzheimer′s disease.

Physical form

Solution in methanol: 10mM aqueous NH4OH (7:3)
Actual concentration given on label

Signal Word

Danger

RIDADR

UN1230 - class 3 - PG 2 - Methanol, solution

WGK Germany

WGK 2

Flash Point(F)

60.8 °F

Flash Point(C)

16 °C

Certificate of Analysis
Certificate of Origin
Petra M Bleeker et al.
Proceedings of the National Academy of Sciences of the United States of America, 109(49), 20124-20129 (2012-11-22)
Tomato breeding has been tremendously efficient in increasing fruit quality and quantity but did not focus on improving herbivore resistance. The biosynthetic pathway for the production of 7-epizingiberene in a wild tomato was introduced into a cultivated greenhouse variety with...
Isoprenoid biosynthesis in the diatom Haslea ostrearia
Kampranis SC and Verret F
The New phytologist, 1-1 (2018)
Chantal Brämer et al.
Biotechnology progress, 35(4), e2812-e2812 (2019-04-02)
The natural production of patchouli oil in developing countries cannot meet the increasing demand any more. This leads to socioecological consequences, such as the use of arable land, which is actually intended for food. Hence, the world market price increased...
Gregory J Reynolds et al.
Plants (Basel, Switzerland), 8(7) (2019-07-25)
Systemic acquired resistance (SAR) is a mechanism through which plants may respond to initial challenge by a pathogen through activation of inducible defense responses, thereby increasing resistance to subsequent infection attempts. Fitness costs are assumed to be incurred by plants...
Matrix metalloproteinase-1 contribution to sarcoma cell invasion
Garamszegi N, et al.
Journal of Cellular and Molecular Medicine, 16(6), 1331-1341 (2012)
Articles
Terpenes comprise the largest and most diverse class of secondary metabolites; approximately 55,000 compounds have been identified to date.
Read More
Biosynthesis of cholesterol generally takes place in the endoplasmic reticulum of hepatic cells and begins with acetyl- CoA, which is mainly derived from an oxidation reaction in the mitochondria. Acetyl-CoA and acetoacetyl-CoA are converted to 3-hydroxy- 3-methylglutaryl-CoA (HMG-CoA) by HMG-CoA synthase.
Read More

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service

Social Media

LinkedIn icon
Twitter icon
Facebook Icon
Instagram Icon

MilliporeSigma

Research. Development. Production.

We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production.

© 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved.

Reproduction of any materials from the site is strictly forbidden without permission.