Geranyl diphosphate

Base Information

• Chemical Name: Geranyl diphosphate
• CAS No.: 763-10-0
• Molecular Formula: C10H20 O7 P2
• Molecular Weight: 314.212
• UNII: 7X7DBM66JG
• DSSTox Substance ID: DTXSID801315430
• Nikkaji Number: J39.583H,J393.135H,J1.452.575K
• Wikipedia: Geranyl_pyrophosphate
• Wikidata: Q418125
• Pharos Ligand ID: 1CB8NDBUDGYP
• Metabolomics Workbench ID: 28001
• ChEMBL ID: CHEMBL41342
• Mol file: 763-10-0.mol

Synonyms:geranyl diphosphate

Chemical Property of Geranyl diphosphate

Chemical Property:

• Vapor Pressure: 1.05E-10mmHg at 25°C
• Boiling Point: 484.2°C at 760 mmHg
• PKA: 1.05±0.50(Predicted)
• Flash Point: 20 °C
• PSA: 132.91000
• Density: 1.342g/cm³
• LogP: 2.90540
• Storage Temp.: −20°C
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 314.06842697
• Heavy Atom Count: 19
• Complexity: 431

Purity/Quality:

98%,99%, ^*data from raw suppliers

Geranyl pyrophosphate ammonium salt 1?mg/mLinmethanol(:aqueous10mMNH4OH(7:3)),≥95%(TLC) ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CCOP(=O)(O)OP(=O)(O)O)C)C
• Isomeric SMILES: CC(=CCC/C(=C/COP(=O)(O)OP(=O)(O)O)/C)C

Technology Process of Geranyl diphosphate

There total 31 articles about Geranyl 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: 92.0%

dimethylallyl diphosphate (358-72-5) + isopentyl pyrophosphate (358-71-4) → geranyl diphosphate (763-10-0)

Guidance literature:

With Artemisia tridentata farnesyl diphosphate synthase C₉ chimera consisting of CPPase sequence from the N-terminus to the 9 junction (S₁₈₂) with the remaining sequence from FPPase; In aq. buffer; at 30 ℃; for 2h; pH=7.6; Enzymatic reaction;

DOI:10.1021/jacs.7b07608

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: 78.0%

tris(tetra-n-butylammonium) hydrogen pyrophosphate (76947-02-9) + 1-chloro-3,7-dimethylocta-2,6-diene (5389-87-7) → geranyl diphosphate (763-10-0)

Guidance literature:

In acetonitrile; for 2h; Ambient temperature;

DOI:10.1021/jo00375a005

upstream raw materials:

Nerol

neryl chloride

tris(tetra-n-butylammonium) hydrogen pyrophosphate

dimethylallyl diphosphate

Downstream raw materials:

(S,2E,6E)-3,4,7,11-tetramethyldodeca-2,6,10-trien-1-ol

(R)-4-methylfarnesol

(3Z,7E)-4,8,12-Trimethyltrideca-3,7,11-trien-1-ol

3,7-dimethylocta-1,6-dien-3-ol

Refernces

Monoterpene biosynthesis. I. Occurrence and mevalonoid origin of gentiopicroside and loganic acid in Swertia caroliniensis

10.1021/bi00840a054

The research investigates the biosynthesis of gentiopicroside and loganic acid, two monoterpene glucosides found in the plant Swertia caroliniensis. The study aims to elucidate their biosynthetic pathways and confirm their mevalonoid origin. Key chemicals used include acetate-2-14C, mevalonate-2-14C, and mevalonate-2-3H-2-14C as labeled precursors. Through tracer experiments and various chemical transformations such as methylation, acetylation, and oxidation, the researchers demonstrated that both compounds originate from mevalonate. They also revised the structure of gentiopicroside based on chemical and spectral data, including double-resonance nuclear magnetic resonance studies. The results support a biogenetic scheme where mevalonate is converted to geranyl pyrophosphate, then to loganic acid, which undergoes ring cleavage to form gentiopicroside. The study concludes that loganic acid and its derivatives play a significant role as precursors for various iridoids and secoiridoids, and potentially for indole alkaloids, highlighting the interconnected biosynthetic pathways of these plant metabolites.

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