3,7,11-Trimethyldodeca-2,6,10-trien-1-yl trihydrogen diphosphate

Base Information

• Chemical Name: 3,7,11-Trimethyldodeca-2,6,10-trien-1-yl trihydrogen diphosphate
• CAS No.: 13058-04-3
• Molecular Formula: C15H28O7P2
• Molecular Weight: 382.331
• Hs Code.: 2905290000
• DSSTox Substance ID: DTXSID10864352
• Wikidata: Q60998692,Q105298044
• Mol file: 13058-04-3.mol

Synonyms:3,7,11-trimethyldodeca-2,6,10-trien-1-yl trihydrogen diphosphate;phosphono 3,7,11-trimethyldodeca-2,6,10-trienyl hydrogen phosphate;farnesylpyrophosphoric acid;SCHEMBL109441;CHEBI:50277;DTXSID10864352;Q60998692;3,7,11-Trimethyl-2,6,10-dodecatrien-1-yl trihydrogen diphosphate

Chemical Property of 3,7,11-Trimethyldodeca-2,6,10-trien-1-yl trihydrogen diphosphate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.513
• Boiling Point: 533.829 °C at 760 mmHg
• PKA: 1.07±0.50(Predicted)
• Flash Point: 276.65 °C
• PSA: 142.63000
• Density: 1.233 g/cm³
• LogP: 5.60360
• Storage Temp.: −20°C
• Solubility.: Methanol (Slightly, Sonicated), Water (Slightly)
• 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%,99%, ^*data from raw suppliers

Farnesyl pyrophosphate triammonium salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=CCCC(=CCCC(=CCOP(=O)(O)OP(=O)(O)O)C)C)C
• Uses: 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

Technology Process of 3,7,11-Trimethyldodeca-2,6,10-trien-1-yl trihydrogen diphosphate

There total 26 articles about 3,7,11-Trimethyldodeca-2,6,10-trien-1-yl trihydrogen 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、 Leyes,Baker,Poulter. "Biosynthesis of isoprenoids in Escherichia coli: stereochemistry of the reaction catalyzed by farnesyl diphosphate synthase.". . p. 1071 - 1073. Retrieved 1999.
• 2、 Yamamoto, Hirotaka,Oritani, Takayuki. "Incorporation of farnesyl pyrophosphate derivertives into abscisic acid and its biosynthetic intermediates in Cercospora cruenta". . p. 821 - 824. Retrieved 1997.
• 3、 Phan,Poulter. "Synthesis of geranyl S-thiolodiphosphate. A new alternative substrate/inhibitor for prenyltransferases.". . p. 2287 - 2289. Retrieved 2000.
• 4、 Dellas, Nikki,Noel, Joseph P.. "Mutation of archaeal isopentenyl phosphate kinase highlights mechanism and guides phosphorylation of additional isoprenoid monophosphates". . p. 589 - 601. Retrieved 2010.
• 5、 Maki, Yuji,Satoh, Hikaru,Kurihara, Masayo,Endo, Takae,Watanabe, Gotaro,Ogura, Kyozo. "Farnesyl Diphosphate Synthase Reactions of Geranyl Diphosphate Analogues Having Oxygen Atoms in Their Alkyl Chains". . p. 1841 - 1844. Retrieved 1994.
• 6、 Lee, J. Scott,Pan, Jian-Jung,Ramamoorthy, Gurusankar,Poulter, C. Dale. "Structure-Function Studies of Artemisia tridentata Farnesyl Diphosphate Synthase and Chrysanthemyl Diphosphate Synthase by Site-Directed Mutagenesis and Morphogenesis". supporting information. p. 14556 - 14567. Retrieved 2017/10/24.