Farnesyl diphosphate

Base Information

• Chemical Name: Farnesyl diphosphate
• CAS No.: 372-97-4
• Molecular Formula: C₁₅H₂₈O₇P₂
• Molecular Weight: 382.331
• UNII: 79W6B01D07
• DSSTox Substance ID: DTXSID701020624
• Nikkaji Number: J348.314B,J647.552C
• Wikipedia: Farnesyl_pyrophosphate
• Wikidata: Q2699676
• Pharos Ligand ID: 22P4FSS9XF9H
• Metabolomics Workbench ID: 28197
• ChEMBL ID: CHEMBL69330
• Mol file: 372-97-4.mol

Synonyms:farnesyl diphosphate;farnesyl pyrophosphate;farnesyl pyrophosphate, (E,E)-isomer;farnesyl pyrophosphate, (E,Z)-isomer;farnesyl pyrophosphate, (Z,E)-isomer;farnesyl pyrophosphate, (Z,Z)-isomer;farnesylpyrophosphate

Chemical Property of Farnesyl diphosphate

Chemical Property:

• XLogP3: 2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 11
• Exact Mass: 382.13102722
• Heavy Atom Count: 24
• Complexity: 568

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CCCC(=CCOP(=O)(O)OP(=O)(O)O)C)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CC/C(=C/COP(=O)(O)OP(=O)(O)O)/C)/C)C
• Recent ClinicalTrials: Nutritional Regulation of Wound Inflammation: Part III

Technology Process of Farnesyl diphosphate

There total 24 articles about Farnesyl diphosphate 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: 88.0%

dimethylallyl diphosphate (358-72-5) + isopentyl pyrophosphate (358-71-4) → geranyl diphosphate (763-10-0) + farnesyl pyrophosphate (372-97-4,13058-04-3,25744-33-6,27248-37-9,27248-38-0,40716-68-5)

Guidance literature:

With farnesyl diphosphate synthase from Artemisia tridentata ssp. Spiciformis; In aq. buffer; at 30 ℃; for 2h; pH=7.6; Reagent/catalyst; Enzymatic reaction;

DOI:10.1021/jacs.7b07608

Reference yield: 72.0%

(2E,6E)-farnesyl chloride (6784-45-8,67023-85-2,72132-86-6,67023-84-1) + tris(tetra-n-butylammonium) hydrogen pyrophosphate (76947-02-9) → farnesyl pyrophosphate (372-97-4,13058-04-3,25744-33-6,27248-37-9,27248-38-0,40716-68-5)

Guidance literature:

In acetonitrile; for 2h; Ambient temperature;

DOI:10.1021/jo00375a005

Reference yield: 70.0%

dimethylallyl diphosphate (358-72-5) + isopentyl pyrophosphate (358-71-4) → geranyl diphosphate (763-10-0) + farnesyl pyrophosphate (372-97-4,13058-04-3,25744-33-6,27248-37-9,27248-38-0,40716-68-5) + (2-cis,6-trans)-farnesyl diphosphate (40716-68-5)

Guidance literature:

With Artemisia tridentata farnesyl diphosphate synthase mutant A₁₆₁I; In aq. buffer; at 30 ℃; for 2h; pH=7.6; Enzymatic reaction;

DOI:10.1021/jacs.7b07608

upstream raw materials:

farnesol

dimethylallyl diphosphate

isopentyl pyrophosphate

dimethylallyl methylenediphosphonate triammonium salt

Downstream raw materials:

(R)-(Z)-α-bisabolene

(-)-β-bisabolene

trichodiene

(+)-α-cuprenene

Refernces

• 1、 Mai, Peter,Zocher, Georg,Stehle, Thilo,Li, Shu-Ming. "Structure-based protein engineering enables prenyl donor switching of a fungal aromatic prenyltransferase". . p. 7461 - 7469. Retrieved 2018/10/24.
• 2、 Gatto, Nathalie,Vattekkatte, Abith,K?llner, Tobias,Degenhardt, J?rg,Gershenzon, Jonathan,Boland, Wilhelm. "Isotope sensitive branching and kinetic isotope effects to analyse multiproduct terpenoid synthases from Zea mays". supporting information. p. 3797 - 3800. Retrieved 2015/03/30.