3,5-Dihydroxycinnamic acid

Base Information

• Chemical Name: 3,5-Dihydroxycinnamic acid
• CAS No.: 127791-54-2
• Molecular Formula: C₉H₈O₄
• Molecular Weight: 180.16
• UNII: 9PD8QLS6G8
• DSSTox Substance ID: DTXSID301030504
• Nikkaji Number: J1.979.587J,J2.370.345I
• Wikipedia: 3,5-Dihydroxycinnamic_acid
• Wikidata: Q4634087
• Mol file: 127791-54-2.mol

Synonyms:3,5-dihydroxycinnamic acid

Chemical Property of 3,5-Dihydroxycinnamic acid

Chemical Property:

• Boiling Point: 431.8±14.0 °C(Predicted)
• PKA: 4.33±0.10(Predicted)
• Density: 1.478±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 180.04225873
• Heavy Atom Count: 13
• Complexity: 202

Purity/Quality:

98% ^*data from raw suppliers

3,5-DihydroxycinnamicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=C(C=C(C=C1O)O)C=CC(=O)O
• Isomeric SMILES: C1=C(C=C(C=C1O)O)/C=C/C(=O)O

Technology Process of 3,5-Dihydroxycinnamic acid

There total 6 articles about 3,5-Dihydroxycinnamic acid 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: 89.0%

(E)-3,5-dimethoxycinnamic acid (20767-04-8) → (2E)-3-(3,5-dihydroxyphenyl)prop-2-enoic acid (127791-54-2,28374-93-8)

Guidance literature:

With boron tribromide; In dichloromethane; at -80 - 20 ℃; for 3h;

DOI:10.1002/bio.3165

Reference yield: 56.0%

malonic acid (141-82-2) + 3,5-dihydroxybenzaldehyde (26153-38-8) → (2E)-3-(3,5-dihydroxyphenyl)prop-2-enoic acid (127791-54-2,28374-93-8)

Guidance literature:

With piperidine; pyridine; at 65 ℃;

DOI:10.1002/cmdc.201800352

Reference yield:

3,5-dimethoxybenzaldehdye (7311-34-4) → (2E)-3-(3,5-dihydroxyphenyl)prop-2-enoic acid (127791-54-2,28374-93-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine / 0.17 h / 20 °C / Inert atmosphere

1.2: 5 h / Reflux; Inert atmosphere

2.1: boron tribromide / dichloromethane / 3.5 h / -78 - 20 °C

With pyridine; boron tribromide; In dichloromethane;

DOI:10.1002/anie.201913023

upstream raw materials:

3,5-diacetoxybenzoyl chloride

malonic acid

(E)-3,5-dimethoxycinnamic acid

3,5-dihydroxybenzaldehyde

Downstream raw materials:

3-(3,5-dimethoxyphenyl)acrylic acid

Refernces

• 1、 Bian, Linglin,Cao, Shining,Cheng, Lihong,Nakazaki, Atsuo,Nishikawa, Toshio,Qi, Jianhua. "Semi-synthesis and Structure–Activity Relationship of Neuritogenic Oleanene Derivatives". supporting information. p. 1972 - 1977. Retrieved 2018/09/06.