GERANYLGERANIOL

Base Information

• Chemical Name: GERANYLGERANIOL
• CAS No.: 24034-73-9
• Molecular Formula: C20H34O
• Molecular Weight: 290.489
• Hs Code.: 29052290
• Mol file: 24034-73-9.mol

Synonyms:2,6,10,14-Hexadecatetraen-1-ol,3,7,11,15-tetramethyl-, (E,E,E)- (8CI);(E,E,E)-Geranylgeraniol;All-trans-Geranylgeraniol;trans,trans,trans-Geranylgeraniol;trans-Geranylgeraniol;

Chemical Property of GERANYLGERANIOL

Chemical Property:

• Appearance/Colour: light yellow oil
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.492
• Boiling Point: 397.1 °C at 760 mmHg
• PKA: 14.42±0.10(Predicted)
• Flash Point: 128.3 °C
• PSA: 20.23000
• Density: 0.88 g/cm³
• LogP: 6.12440
• Storage Temp.: −20°C
• Solubility.: Chloroform (Sparingly), Dichloromethane (Slightly), Ethyl Acetate (Slightly), He

Purity/Quality:

97% ^*data from raw suppliers

Geranylgeraniol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Geranylgeraniol, a precursor to Geranylgeranylpyrophosphate (G367600), is an intermediate in the mevalonate pathway. Geranylgeraniol has been shown to prevent bone re-adsorption, inhibition of osteocl ast formation, and kinase activation in vitro. Geranylgeraniol, a precursor to Geranylgeranylpyrophosphate (G367600), is an intermediate in the mevalonate pathway. Geranylgeraniol has been shown to prevent bone re-adsorption, inhibition of osteoclast formation, and kinase activation in vitro.

Technology Process of GERANYLGERANIOL

There total 2 articles about GERANYLGERANIOL 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:

dimethylallyl diphosphate (358-72-5) + isopentyl pyrophosphate (358-71-4) → Farnesol (106-28-5) + Geranylgeraniol (24034-73-9)

Guidance literature:

dimethylallyl diphosphate; isopentyl pyrophosphate; With DL-dithiothreitol; ammonium chloride; magnesium chloride; at 37 ℃; for 1h; pH=8.5; Enzymatic reaction;

In isopropyl alcohol; at 37 ℃; for 12h; Enzymatic reaction;

DOI:10.1002/cbic.201500138

Reference yield:

1-chloro-3,7-dimethylocta-2,6-diene (5389-87-7) → Geranylgeraniol (24034-73-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) lithium biphenylide, barium iodide / 1) THF, -78 deg C, 30 min, 2) THF, a) -78 deg C, 1.5 h, b) room temperature, 16 h

2: 95 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 16 h / 23 °C

With lithium biphenylide; barium(II) iodide; tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)79008-3

Reference yield: 100.0%

Geranylgeraniol (24034-73-9) + triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → C29H54OSi

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1002/anie.202104051

upstream raw materials:

1-chloro-3,7-dimethylocta-2,6-diene

dimethylallyl diphosphate

isopentyl pyrophosphate

Downstream raw materials:

2E,6E,10E-geranylgeranyl aldehyde

2E,6E,10E-geranylgeranyl bromide

β-springene

(E,E,E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl 4-nitrobenzoate