4,5-Dihydroxy-3-methoxycinnamaldehyde

Base Information

• Chemical Name: 4,5-Dihydroxy-3-methoxycinnamaldehyde
• CAS No.: 249647-14-1
• Molecular Formula: C₁₀H₁₀O₄
• Molecular Weight: 194.187
• DSSTox Substance ID: DTXSID001313359
• Mol file: 249647-14-1.mol

Synonyms:SCHEMBL151754;DTXSID001313359;4,5-dihydroxy-3-methoxycinnamaldehyde

Chemical Property of 4,5-Dihydroxy-3-methoxycinnamaldehyde

Chemical Property:

• Vapor Pressure: 1.74E-07mmHg at 25°C
• Boiling Point: 415.2°Cat760mmHg
• Flash Point: 169.8°C
• PSA: 66.76000
• Density: 1.306g/cm³
• LogP: 1.31850
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 194.05790880
• Heavy Atom Count: 14
• Complexity: 214

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1O)O)C=CC=O

Technology Process of 4,5-Dihydroxy-3-methoxycinnamaldehyde

There total 13 articles about 4,5-Dihydroxy-3-methoxycinnamaldehyde 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: 95.0%

(E)-3-methoxy-5-(3-oxoprop-1-en-1-yl)-1,2-phenylene diacetate (340010-10-8) → (E)-3-(3,4-dihydroxy-5-methoxyphenyl)acrylaldehyde (266999-89-7,249647-14-1)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; at 20 ℃;

DOI:10.1002/jccs.200100011

Reference yield: 82.0%

3-methoxy-4,5-diacetoxycinnamaldehyde → 5-hydroxyconiferyl aldehyde (249647-14-1)

Guidance literature:

With sodium hydrogencarbonate; In methanol; water; at 20 ℃; for 12h;

Reference yield:

5-Hydroxyeugenol (4055-72-5) → (E)-3-(3,4-dihydroxy-5-methoxyphenyl)acrylaldehyde (266999-89-7,249647-14-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 88 percent / PdCl₂ / methanol

2.1: pyridine / CH₂Cl₂

2.2: 72 percent / SeO₂ / ethanol / 4 h / Heating

3.1: 95 percent / aq. NaHCO₃ / methanol / 20 °C

With pyridine; sodium hydrogencarbonate; palladium dichloride; In methanol; dichloromethane;

DOI:10.1002/jccs.200400149

upstream raw materials:

5-Hydroxyeugenol

(E)-3-methoxy-5-(3-oxoprop-1-en-1-yl)-1,2-phenylene diacetate

3-methocycatechol

2-allyloxy-3-methoxy-phenol

Refernces

• 1、 Jiang, Tao-Shan,Zhang, Qingqing,Li, Guohui,Cheng, Xi,Cai, Yongping. "DDQ-mediated oxidation of allylarenes: Expedient access to cinnamaldehyde-containing phenylpropanoids". . p. 4611 - 4616. Retrieved 2019/02/01.
• 2、 Jing, Xiaobi,Gu, Wenxin,Ren, Xinfeng,Bie, Pingyan,Pan, Xinfu. "Total synthesis of (±)-Eusiderin G and (±)-Eusiderin M". . p. 59 - 63. Retrieved 2007/10/03.