3-Methyl-1-(2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl)butan-1-one

Base Information

• Chemical Name: 3-Methyl-1-(2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl)butan-1-one
• CAS No.: 54614-64-1
• Molecular Formula: C16H22O4
• Molecular Weight: 278.34300
• DSSTox Substance ID: DTXSID90539955
• Nikkaji Number: J1.061.561E
• Mol file: 54614-64-1.mol

Synonyms:54614-64-1;4-prenylphlorisovalerophenone;3-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-enyl)phenyl]butan-1-one;3-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-1-butanone;3-Methyl-1-(2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl)butan-1-one;3-Methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]butan-1-one;starbld0022492;DTXSID90539955;CHEBI:134341;2-isovaleryl-4-prenylphloroglucinol;2-isopentanoyl-4-prenylphloroglucinol;AKOS030255105;2-(3-methylbutanoyl)-4-prenylphloroglucinol;2',4',6'-trihydroxy-3'-(3-methylbut-2-enyl)isovalerophenone

Chemical Property of 3-Methyl-1-(2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl)butan-1-one

Chemical Property:

• PSA: 77.76000
• LogP: 3.54090
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 278.15180918
• Heavy Atom Count: 20
• Complexity: 358

Purity/Quality:

3-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-1-butanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(=O)C1=C(C=C(C(=C1O)CC=C(C)C)O)O
• Uses: 3-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-1-butanone is an impurity in the synthesis of Lupulone (L478000), a hop plant (Humulus lupulus L.) acid that inhibits tumorigenicity of hepatocellular carcinoma cells.

Technology Process of 3-Methyl-1-(2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl)butan-1-one

There total 8 articles about 3-Methyl-1-(2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl)butan-1-one 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: 16.47%

dimethylallyl diphosphate (358-72-5) + phloroisovalerophenone (26103-97-9) → 2',4',6'-trihydroxy-3'-(3-methylbut-2-enyl)isovalerophenone (54614-64-1) + C16H22O4 + C21H30O4 + 3,3-di(2-isopentenyl)phloroisovalerophenone

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:

phloroisovalerophenone (26103-97-9) + prenyl bromide (870-63-3) → deoxyhumulone (4374-93-0) + lupulone + 2',4',6'-trihydroxy-3'-(3-methylbut-2-enyl)isovalerophenone (54614-64-1)

Guidance literature:

Reference yield:

methanol (67-56-1) + phloroisovalerophenone (26103-97-9) + sodium methylate (124-41-4) + prenyl bromide (870-63-3) → deoxyhumulone (4374-93-0) + lupulone + 2',4',6'-trihydroxy-3'-(3-methylbut-2-enyl)isovalerophenone (54614-64-1)

Guidance literature:

upstream raw materials:

methanol

phloroisovalerophenone

sodium methylate

prenyl bromide

Downstream raw materials:

3-methyl-1-(2,4,6-trihydroxy-3-isopentylphenyl)butan-1-one

4-isopentyl-6-(3-methylbut-2-enyl)-3,5,6-trihydroxy-2-isovalerylcyclohexa-2,4-dien-1-one

2',4',6'-trihydroxy-3'-isopentyl-5'-(3-methylbut-2-enyl)isovalerophenone

6-isopentyl-4-(3-methylbut-2-enyl)-3,5,6-trihydroxy-2-isovalerylcyclohexa-2,4-dien-1-one

Refernces

• 1、 Zhou, Kang,Ludwig, Lena,Li, Shu-Ming. "Friedel-Crafts Alkylation of Acylphloroglucinols Catalyzed by a Fungal Indole Prenyltransferase". . p. 929 - 933. Retrieved 2015/05/05.