Dimethylallyl diphosphate

Base Information

• Chemical Name: Dimethylallyl diphosphate
• CAS No.: 358-72-5
• Molecular Formula: C5H12 O7 P2
• Molecular Weight: 246.094
• Hs Code.: 2905290000
• DSSTox Substance ID: DTXSID70189331
• Nikkaji Number: J39.581A
• Wikipedia: Dimethylallyl_pyrophosphate
• Wikidata: Q417398
• Metabolomics Workbench ID: 27998
• ChEMBL ID: CHEMBL343480
• Mol file: 358-72-5.mol

Synonyms:3,3-dimethylallyl pyrophosphate;3,3-dimethylallyl pyrophosphate, (14)C-labeled;dimethylallyl diphosphate;DMADP cpd;DMAPP

Chemical Property of Dimethylallyl diphosphate

Chemical Property:

• Vapor Pressure: 4.12E-15mmHg at 25°C
• Boiling Point: 417°Cat760mmHg
• Flash Point: 206°C
• PSA: 132.91000
• Density: 1.557g/cm³
• LogP: 1.17890
• Storage Temp.: −20°C
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 246.00582671
• Heavy Atom Count: 14
• Complexity: 299

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Hazard Codes: T
• Statements: 10-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

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

Technology Process of Dimethylallyl diphosphate

There total 11 articles about Dimethylallyl 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: 91.0%

prenyl bromide (870-63-3) → dimethylallyl diphosphate (358-72-5)

Guidance literature:

prenyl bromide; With tris(tetra-n-butylammonium) hydrogen pyrophosphate; In acetonitrile; at -35 ℃; for 0.166667h;

DOI:10.1002/anie.201902910

Reference yield: 80.0%

tris(tetra-n-butylammonium) hydrogen pyrophosphate (76947-02-9) + prenyl bromide (870-63-3) → dimethylallyl diphosphate (358-72-5)

Guidance literature:

In acetonitrile; for 2h; Ambient temperature;

DOI:10.1021/jo00375a005

Reference yield:

isopentyl pyrophosphate (358-71-4) → dimethylallyl diphosphate (358-72-5)

Guidance literature:

With dipotassium hydrogenphosphate; potassium chloride; magnesium chloride; diothiothreitol; In water; at 24 ℃; Kinetics; Saccharomyces cerevisiae IPP isomerase;

DOI:10.1021/ja00179a049

upstream raw materials:

phosphoramidic acid mono-(3-methyl-but-2-enyl) ester

tris(tetra-n-butylammonium) hydrogen pyrophosphate

prenyl bromide

isopentyl pyrophosphate

Downstream raw materials:

terpineol

limonene.

(S)-2-amino-3-(4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl)propanoic acid

6,6-dimethyldihydropyran (2,3:7,8)-5,4'-dihydroxyflavonol

Refernces

• 1、 Takagi, Motoki,Kaneda, Kazuhide,Shimizu, Tomohiro,Hayakawa, Yoichi,Seto, Haruo,Kuzuyama, Tomohisa. "Bacillus subtilis ypgA gene is fni, a nonessential gene encoding type 2 isopentenyl diphosphate isomerase". . p. 132 - 137. Retrieved 2004.
• 2、 Wu, Zheng,Wouters, Johan,Poulter, C. Dale. "Isopentenyl diphosphate isomerase. Mechanism-based inhibition by diene analogues of isopentenyl diphosphate and dimethylallyl diphosphate". . p. 17433 - 17438. Retrieved 2005.
• 3、 Allemann, Rudolf K.,Benton, Jennifer C. R.,Dunbabin, Alice,Johnson, Luke A.,Mart, Robert J.. "Modular Chemoenzymatic Synthesis of Terpenes and their Analogues". supporting information. p. 8486 - 8490. Retrieved 2020/03/30.
• 4、 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.