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F6892

Sigma-Aldrich

Farnesyl pyrophosphate ammonium salt

methanol:ammonia solution, ≥95% (TLC)

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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

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)

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This Item
G6772G602544270
Geranyl pyrophosphate ammonium salt 1 mg/mL in methanol (:aqueous 10 mM NH4OH (7:3)), ≥95% (TLC)

G6772

Geranyl pyrophosphate ammonium salt

form

methanol:ammonia solution

form

liquid

form

solution

form

solid

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

packaging

vial of 200 μg

packaging

vial of 200 μg

packaging

vial of 200 μg

packaging

-

Gene Information

rat ... Fnta(25318)

Gene Information

-

Gene Information

-

Gene Information

-

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

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

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Chronic 3 - Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 1

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

60.8 °F

flash_point_c

16 °C


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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
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
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
Audrey Holland et al.
American journal of speech-language pathology, 28(3), 1010-1018 (2019-05-24)
Purpose This clinical focus article describes the development and use of the Famous People Protocol (FPP), a clinical tool for observing the strategies people with severe aphasia (PWSA) can use to communicate when speech is limited. Its goal is to

Articles

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.

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