Prenyl caffeate

Base Information

• Chemical Name: Prenyl caffeate
• CAS No.: 118971-61-2
• Molecular Formula: C14H16 O4
• Molecular Weight: 248.27
• ChEMBL ID: CHEMBL471184
• Metabolomics Workbench ID: 49266
• Nikkaji Number: J367.543B,J405.580B
• Wikidata: Q27108066
• Mol file: 118971-61-2.mol

Synonyms:1,1-DACAE;1,1-dimethylallyl caffeic acid ester;3-methyl-2-butenyl caffeate;3-methylbut-2-enyl caffeate;isoprenyl caffeate;3-methyl-3-butenyl caffeate;prenyl caffeate

Chemical Property of Prenyl caffeate

Chemical Property:

• Melting Point: 126 °C
• Boiling Point: 417.5°Cat760mmHg
• PKA: 9.33±0.10(Predicted)
• Flash Point: 156.1°C
• PSA: 66.76000
• Density: 1.201g/cm³
• LogP: 2.62040
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 248.10485899
• Heavy Atom Count: 18
• Complexity: 329

Purity/Quality:

98%Min ^*data from raw suppliers

Caffeic acid 1,1-dimethylallyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCOC(=O)C=CC1=CC(=C(C=C1)O)O)C
• Isomeric SMILES: CC(=CCOC(=O)/C=C/C1=CC(=C(C=C1)O)O)C
• Uses: Caffeic Acid 1,1-Dimethylallyl Ester can be used in biological study for chemical properties and antioxidant and antimicrobial activities of Slovenian propolis. Caffeic Acid 1,1-Dimethylallyl Ester can also be used for biological activity and study for synthesis and evaluation of caffeic acid amides as antioxidants.

Technology Process of Prenyl caffeate

There total 2 articles about Prenyl caffeate 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: 42.0%

caffeic acid (331-39-5,501-16-6) + 3-methyl-2-buten-1-ol (556-82-1) → (E)-3-methylbut-2-en-1-yl 3-(3,4-dihydroxyphenyl)acrylate (118971-61-2)

Guidance literature:

With di-isopropyl azodicarboxylate; thiamine diphosphate; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/ol0266471

Reference yield:

→ (E)-3-methylbut-2-en-1-yl 3-(3,4-dihydroxyphenyl)acrylate (118971-61-2)

Guidance literature:

With aqueous acids; Hydrolysis;

upstream raw materials:

caffeic acid

3-methyl-2-buten-1-ol

Refernces

• 1、 Uwai, Koji,Osanai, Yuu,Imaizumi, Takuma,Kanno, Syu-ichi,Takeshita, Mitsuhiro,Ishikawa, Masaaki. "Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages". . p. 7795 - 7803. Retrieved 2008/12/23.