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F6892

Sigma-Aldrich

Farnesyl pyrophosphate ammonium salt

methanol:ammonia solution, ≥95% (TLC)

Sinónimos:

3,7,11-Trimethyl-2,6,10-dodecatrien-1-yl pyrophosphate ammonium salt, FPP

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1 VIAL
US$ 136,00
5 VIALS
US$ 469,00

US$ 136,00

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About This Item

Fórmula empírica (notación de Hill):
C15H37N3O7P2
Número de CAS:
13058-04-3
Peso molecular:
433.42
Número MDL:
MFCD00189688
Código UNSPSC:
12352204
ID de la sustancia en PubChem:
24894923
NACRES:
NA.83

US$ 136,00

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Ensayo

≥95% (TLC)

Formulario

methanol:ammonia solution

envase

vial of 200 μg

temp. de almacenamiento

−20°C

cadena SMILES

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+

Clave InChI

VWFJDQUYCIWHTN-YFVJMOTDSA-N

Información sobre el gen

rat ... Fnta(25318)

Categorías relacionadas

Descripción general

Farnesyl pyrophosphate is a 15-carbon isoprenoid synthesized from geranyl pyrophosphate (GPP) by the action of enzyme farnesyl pyrophosphate synthase (FPPS).[1]

Aplicación

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]

Acciones bioquímicas o fisiológicas

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]

Forma física

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

Palabra de señalización

Danger

Clasificaciones de peligro

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

Órganos de actuación

Eyes,Central nervous system

Código de clase de almacenamiento

3 - Flammable liquids

Clase de riesgo para el agua (WGK)

WGK 2

Punto de inflamabilidad (°F)

60.8 °F

Punto de inflamabilidad (°C)

16 °C

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Certificados de análisis (COA)

Lot/Batch Number
MKCX1846
MKCV8524
MKCV8393
MKCT0819
MKCV1899

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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)
Matrix metalloproteinase-1 contribution to sarcoma cell invasion
Garamszegi N, et al.
Journal of Cellular and Molecular Medicine, 16(6), 1331-1341 (2012)
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
Protein prenylation: enzymes, therapeutics, and biotechnology applications
Palsuledesai CC and Distefano MD
ACS Chemical Biology, 10(1), 51-62 (2014)
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
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Artículos

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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