4-Acetoxy-3,5-dimethoxybenzaldehyde

Base Information

• Chemical Name: 4-Acetoxy-3,5-dimethoxybenzaldehyde
• CAS No.: 53669-33-3
• Molecular Formula: C11H12O5
• Molecular Weight: 224.213
• Hs Code.: 2915390090
• European Community (EC) Number: 611-030-4
• DSSTox Substance ID: DTXSID70350822
• Nikkaji Number: J267.349E
• Wikidata: Q27159287
• Metabolomics Workbench ID: 70036
• Mol file: 53669-33-3.mol

Synonyms:53669-33-3;4-Acetoxy-3,5-dimethoxybenzaldehyde;4-formyl-2,6-dimethoxyphenyl acetate;Syringaldehyde acetate;(4-formyl-2,6-dimethoxyphenyl) acetate;MFCD00016604;4-acetoxy-3,5-dimethoxy benzaldehyde;ACMC-20amq7;ZINC00056855;O-acetylsyringaldehyde;4-Acetyl syringaldehyde;Benzaldehyde, 4-(acetyloxy)-3,5-dimethoxy-;bmse010133;acetic acid 4-formyl-2,6-dimethoxy-phenyl ester;SCHEMBL3395431;CHEBI:86945;DTXSID70350822;BBL023476;STL225135;3,5-dimethoxy-4-acetoxy-benzaldehyde;AKOS000120863;AT10285;3,5-Dimethoxy-4-(acetyl)oxybenzaldehyde;(4-formyl-2,6-dimethoxy-phenyl) acetate;SY162915;VS-07442;4-Acetoxy-3,5-dimethoxybenzaldehyde, 98%;CS-0204284;FT-0617386;EN300-18412;A829720;Q27159287;Z57887900

Chemical Property of 4-Acetoxy-3,5-dimethoxybenzaldehyde

Chemical Property:

• Vapor Pressure: 0.000705mmHg at 25°C
• Melting Point: 115-117 °C(lit.)
• Refractive Index: 1.53
• Boiling Point: 307.9 °C at 760 mmHg
• Flash Point: 152.3 °C
• PSA: 61.83000
• Density: 1.2 g/cm³
• LogP: 1.44160
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly),Methanol (Slightly)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 224.06847348
• Heavy Atom Count: 16
• Complexity: 239

Purity/Quality:

98%min ^*data from raw suppliers

4-Acetoxy-3,5-dimethoxybenzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1=C(C=C(C=C1OC)C=O)OC

Technology Process of 4-Acetoxy-3,5-dimethoxybenzaldehyde

There total 12 articles about 4-Acetoxy-3,5-dimethoxybenzaldehyde 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: 99.8%

acetic anhydride (108-24-7) + syringic aldehyde (134-96-3) → 4-acetoxy-3,5-dimethoxybenzaldehyde (53669-33-3)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃;

DOI:10.1039/c5ra21313d

Reference yield: 99.8%

4,4'-hydrazine-1,2-diylidenebis(methan-1-yl-1-ylidene)bis(2,6-dimethoxyphenol) (14414-32-5) + acetic anhydride (108-24-7) → 4-acetoxy-3,5-dimethoxybenzaldehyde (53669-33-3)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.bmc.2019.04.027

Reference yield:

3,4,5-trimethoxy-benzaldehyde (86-81-7) → 4-acetoxy-3,5-dimethoxybenzaldehyde (53669-33-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / piperidine / H₂O / 20 h / Heating

2: pyridine

With piperidine; pyridine; In water;

upstream raw materials:

O-acetylsyringic acid chloride

acetic anhydride

2,3,4-Tri-O-acetyl-α-L-fucopyranosyl chloride

syringic aldehyde

Downstream raw materials:

3,5-Dimethoxy-4-acetoxy-α-nitromethyl-benzylalkohol

3-(4'-acetoxy-3',5'-dimethoxy)benzylidene-1,2-dihydropyrrolo[2.1-b]quinazoline-9-one

syringic alcohol

2,6-dimethoxy-4-methylphenol

Refernces

• 1、 Dong, Hongbo,Du, Weihong,He, Yujiao,Shi, Zheng,Wang, Yingying,Wu, Min. "Total Syntheses and Anti-inflammatory Activities of Syringin and Its Natural Analogues". . p. 2866 - 2874. Retrieved 2021/11/12.
• 2、 Horbury,Flourat,Greenough,Allais,Stavros. "Investigating isomer specific photoprotection in a model plant sunscreen". supporting information. p. 936 - 939. Retrieved 2018/02/07.