2-Geranyl-4-isobutyrylphloroglucinol

Base Information

• Chemical Name: 2-Geranyl-4-isobutyrylphloroglucinol
• CAS No.: 72008-03-8
• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.44
• Mol file: 72008-03-8.mol

Synonyms:2-Geranyl-4-isobutyrylphloroglucinol;3-Geranyl-1-(2'-methylpropanoyl)phloroglucinol;2-Geranyl-4-(2-methylpropanoyl)phloroglucinol

Chemical Property of 2-Geranyl-4-isobutyrylphloroglucinol

Chemical Property:

• Boiling Point: 491.6±45.0 °C(Predicted)
• PKA: 7.76±0.50(Predicted)
• PSA: 77.76000
• Density: 1.103±0.06 g/cm3(Predicted)
• LogP: 4.87730

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Geranyl-4-isobutyrylphloroglucinol

There total 3 articles about 2-Geranyl-4-isobutyrylphloroglucinol 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: 55.0%

trans-geranyl bromide (6138-90-5) + phlorisobutyrophenone (35458-21-0) → (E)-1-(3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4,6-trihydroxyphenyl)-2-methylpropan-1-one (72008-03-8,72008-05-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 48h; Inert atmosphere;

DOI:10.1016/j.tet.2011.09.075

Reference yield: 32.85%

geranyl diphosphate (763-10-0) + phlorisobutyrophenone (35458-21-0) → 1-(4-(E-3,7-dimethylocta-2,6-dienyloxy)-2.6-dihydroxylphenyl)-2-methylpropan-1-one (71539-65-6) + (E)-1-(3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4,6-trihydroxyphenyl)-2-methylpropan-1-one (72008-03-8,72008-05-0)

Guidance literature:

With Aspergillus terreus aromatic prenyltransferase; calcium chloride; In dimethyl sulfoxide; glycerol; at 37 ℃; for 2h; pH=7.5; Enzymatic reaction;

DOI:10.1021/acs.orglett.6b03594

Reference yield:

3,5-dihydroxyphenol (108-73-6) → (E)-1-(3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4,6-trihydroxyphenyl)-2-methylpropan-1-one (72008-03-8,72008-05-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: aluminum (III) chloride / carbon disulfide; nitrobenzene / 1 h / 55 °C

1.2: 1 h / 55 °C

2.1: potassium carbonate / acetone / 24 h / Reflux

With aluminum (III) chloride; potassium carbonate; In carbon disulfide; nitrobenzene; acetone; 1.1: |Friedel-Crafts Acylation;

DOI:10.1016/j.ejmech.2014.08.017

upstream raw materials:

trans-geranyl bromide

phlorisobutyrophenone

3,5-dihydroxyphenol

geranyl diphosphate

Downstream raw materials:

(E)-2-(3,7-dimethylocta-2,6-dienyl)-4-isobutyrylbenzene-1,3,5-triyl triacetate

Refernces

• 1、 Zhou, Kang,Wunsch, Carsten,Dai, Jungui,Li, Shu-Ming. "gem-Diprenylation of Acylphloroglucinols by a Fungal Prenyltransferase of the Dimethylallyltryptophan Synthase Superfamily". supporting information. p. 388 - 391. Retrieved 2017/04/21.
• 2、 Sun, Qiu,Schmidt, Sebastian,Tremmel, Martina,Heilmann, J?rg,K?nig, Burkhard. "Synthesis of natural-like acylphloroglucinols with anti-proliferative, anti-oxidative and tube-formation inhibitory activity". . p. 621 - 628. Retrieved 2014/10/15.