Farnesyl phosphate

Base Information

• Chemical Name: Farnesyl phosphate
• CAS No.: 15416-91-8
• Molecular Formula: C15H27 O4 P
• Molecular Weight: 302.351
• DSSTox Substance ID: DTXSID101137758
• Nikkaji Number: J684.104J
• Wikidata: Q27162417
• Mol file: 15416-91-8.mol

Synonyms:farnesyl monophosphate

Chemical Property of Farnesyl phosphate

Chemical Property:

• Vapor Pressure: 5.09E-09mmHg at 25°C
• Boiling Point: 441.3°Cat760mmHg
• Flash Point: 220.7°C
• PSA: 76.57000
• Density: 1.072g/cm³
• LogP: 4.51490
• Storage Temp.: ?20°C
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 302.16469634
• Heavy Atom Count: 20
• Complexity: 412

Purity/Quality:

99% ^*data from raw suppliers

trans,trans-Farnesyl monophosphate ammonium salt ≥95.0% (TLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CCCC(=CCOP(=O)(O)O)C)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CC/C(=C/COP(=O)(O)O)/C)/C)C
• General Description: Farnesyl monophosphate, also known as farnesyl phosphate or trans,trans-farnesylmonophosphate, is an intermediate in biosynthetic pathways, and its acid-catalyzed decomposition proceeds via an essentially unassisted ionization mechanism, with minimal intramolecular involvement from the C-6/C-7 double bond, as evidenced by kinetic isotope effects and product analysis.

Technology Process of Farnesyl phosphate

There total 3 articles about Farnesyl phosphate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

Farnesol (106-28-5) → (2Z,6E)-3-methyl-7,11-dimethyldodeca-2,6,10-triene monophosphate (15416-91-8)

Guidance literature:

With pyruvate kinase; phosphoenolpyruvic acid; undecaprenol kinase; ATP; 2-amino-2-hydroxymethyl-1,3-propanediol; magnesium chloride; at 37 ℃; for 24h; pH=8; Kinetics; Enzymatic reaction;

DOI:10.1002/anie.201402313

Reference yield:

farnesol (4602-84-0) → Farnesylphosphat (15416-86-1,15416-91-8,64354-62-7)

Guidance literature:

Multistep reaction; (i) H₃PO₄, Et₃N, CCl₃CN, MeCN, (ii) NH₃;

Reference yield:

→ (2Z,6E)-3-methyl-7,11-dimethyldodeca-2,6,10-triene monophosphate (15416-91-8)

Guidance literature:

Farnesoe, Trichloracetonitril, Bis-(triaethylammonium)-phosphat;

DOI:10.1021/bi00764a002

upstream raw materials:

farnesol

Farnesol

Downstream raw materials:

farnesyl pyrophosphate

Refernces

The mechanism of the acid-catalyzed decomposition of the farnesyl phosphates

10.1016/0040-4020(77)80182-8

The research investigates the mechanism of the acid-catalyzed decomposition of farnesyl phosphates, aiming to determine whether the ionization of (Z,E)-farnesyl phosphate involves intramolecular assistance from the C-6/C-7 double bond or occurs via an unassisted process. The study examines the rates and products of the decomposition of various farnesyl phosphates, including (Z,E)- and (E,E)-farnesyl phosphate, their deuterated analogs, and t-butyl phosphate. The key chemicals used are farnesyl phosphates synthesized through different methods, formic acid for formolysis, various buffers for hydrolysis, and tetramethylammonium hydroxide for preparing phosphate solutions. The researchers measured the dissociation constants of the farnesyl phosphates and the rates of their acid-catalyzed decomposition. They also analyzed the product compositions and observed secondary deuterium kinetic isotope effects. The results show that while there is some evidence supporting both possibilities, the isotope data suggest that the ionization involves little to no assistance from the double bond, leading to the conclusion that the reaction is best viewed as an essentially unassisted process.