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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

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About This Item

Empirical Formula (Hill Notation):
C15H37N3O7P2
CAS Number:
13058-04-3
Molecular Weight:
433.42
MDL number:
MFCD00189688
UNSPSC Code:
12352204
PubChem Substance ID:
24894923
NACRES:
NA.83

$108.00

In StockDetails

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Quality Level

100

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).[1]

Application

Farnesyl pyrophosphate ammonium salt has been used:
  • as a prenylation agonist in human osteogenic sarcoma cells in collagen-based cell invasion assays [2]
  • in the prenylation of the hepatocyte growth factor (HGF) in human umbilical vein endothelial cells (HUVECs)[3]
  • as a substrate in prenyltransferases assay in diatom Haslea ostrearia[4]

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.[1] FPP is essential for cell survival[5] and is used for prenylation of several low molecular mass G proteins, including Ras.[6] Inhibition of prenylation results in loss of oncogenic potential of Ras proteins.[7] Inhibition of prenylation may serve as therapeutic potential for management of synaptic plasticity and Alzheimer′s disease.[6]

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

target_organs

Eyes,Central nervous system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

60.8 °F

flash_point_c

16 °C

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX1846
MKCV8524
MKCV8393
MKCT0819
MKCV1899

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Matrix metalloproteinase-1 contribution to sarcoma cell invasion
Garamszegi N, et al.
Journal of Cellular and Molecular Medicine, 16(6), 1331-1341 (2012)
Protein prenylation: enzymes, therapeutics, and biotechnology applications
Palsuledesai CC and Distefano MD
ACS Chemical Biology, 10(1), 51-62 (2014)
John M Sanders et al.
Journal of medicinal chemistry, 48(8), 2957-2963 (2005-04-15)
We report the design, synthesis and testing of a series of novel bisphosphonates, pyridinium-1-yl-hydroxy-bisphosphonates, based on the results of comparative molecular similarity indices analysis and pharmacophore modeling studies of farnesyl diphosphate synthase (FPPS) inhibition, human Vgamma2Vdelta2 T cell activation and
Structural characterization of substrate and inhibitor binding to farnesyl pyrophosphate synthase from Pseudomonas aeruginosa
Schmidberger JW, et al.
Acta Crystallographica Section D, Biological Crystallography, 71(3), 721-731 (2015)
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
View All Related Papers

Articles

Cholesterol Biosynthesis

Cholesterol biosynthesis starts in the hepatic endoplasmic reticulum with acetyl-CoA, yielding 3-hydroxy-3-methylglutaryl-CoA via HMG-CoA synthase.

Questions

1–3 of 3 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  3. What is the molarity for the product under the product number F6892

    1 answer

    1. The concentration was reported as 1 mg/ml, resulting in a calculated molarity of 2.31 mM based on the molecular weight of 433.42 g/mol. The calculation is as follows: 1M is equivalent to 433.42 g in 1L, thus 1 M is equivalent to 433.42 mg in 1ml, and consequently 1 mg/ml is approximately 2.307 mM.

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