Propyl 4-hydroxy-3-methoxyphenylacetate

Base Information

• Chemical Name: Propyl 4-hydroxy-3-methoxyphenylacetate
• CAS No.: 52744-26-0
• Molecular Formula: C12H16 O4
• Molecular Weight: 224.257
• European Community (EC) Number: 258-151-5
• DSSTox Substance ID: DTXSID40200729
• Nikkaji Number: J295.783C
• Wikidata: Q83073891
• ChEMBL ID: CHEMBL3819069
• Mol file: 52744-26-0.mol

Synonyms:Propyl 4-hydroxy-3-methoxyphenylacetate;52744-26-0;propyl 2-(4-hydroxy-3-methoxyphenyl)acetate;EINECS 258-151-5;Homovanillinsaure-n-propylester;SCHEMBL1878488;Benzeneacetic acid, 4-hydroxy-3-methoxy-, propyl ester;CHEMBL3819069;DTXSID40200729;AKOS028110734;3-methoxy-4-hydroxyphenylacetic Acid Propyl Ester;4-Hydroxy-3-methoxybenzeneacetic acid propyl ester

Chemical Property of Propyl 4-hydroxy-3-methoxyphenylacetate

Chemical Property:

• Vapor Pressure: 5.73E-05mmHg at 25°C
• Boiling Point: 336.5°C at 760 mmHg
• Flash Point: 124.4°C
• PSA: 55.76000
• Density: 1.134g/cm³
• LogP: 1.89650
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 224.10485899
• Heavy Atom Count: 16
• Complexity: 217

Purity/Quality:

98%Min ^*data from raw suppliers

HomovanillicAcidPropylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCOC(=O)CC1=CC(=C(C=C1)O)OC
• Uses: Homovanillic Acid Propyl Ester, is an intermediate in the synthesis of Sombrevin (S676765), which is an anesthetic agent.

Technology Process of Propyl 4-hydroxy-3-methoxyphenylacetate

There total 4 articles about Propyl 4-hydroxy-3-methoxyphenylacetate 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: 78.2%

propan-1-ol (71-23-8) + Homovanillic acid (306-08-1) → Propyl-2-(4-hydroxy-3-methoxy-phenyl)acetate (52744-26-0)

Guidance literature:

With acetyl chloride; at 60 ℃; for 3h;

DOI:10.1016/j.bmcl.2016.06.028

Reference yield:

2-methoxy-phenol (90-05-1) → Propyl-2-(4-hydroxy-3-methoxy-phenyl)acetate (52744-26-0)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydroxide / water

2: 5%-palladium/activated carbon; hydrogen; acetic acid / water

3: sulfuric acid / 7 h / 90 °C

With sulfuric acid; 5%-palladium/activated carbon; hydrogen; acetic acid; sodium hydroxide; In water;

DOI:10.3390/molecules24193599

Reference yield:

4-hydroxy-3-methoxy-mandelic acid (55-10-7,2394-20-9) → Propyl-2-(4-hydroxy-3-methoxy-phenyl)acetate (52744-26-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 5%-palladium/activated carbon; hydrogen; acetic acid / water

2: sulfuric acid / 7 h / 90 °C

With sulfuric acid; 5%-palladium/activated carbon; hydrogen; acetic acid; In water;

DOI:10.3390/molecules24193599

upstream raw materials:

propan-1-ol

Homovanillic acid

2-methoxy-phenol

4-hydroxy-3-methoxy-mandelic acid

Downstream raw materials:

propanidid

Refernces

• 1、 -. "HOMOVANILLIC ESTER, MORE PARTICULARLY FOR ACHIEVING AN IMPRESSION OF HEAT AND/OR SPICINESS". Paragraph 0195; 0196; 0213-0216. . Retrieved 2019/09/20.
• 2、 Ishimata, Nao,Ito, Hideyuki,Tai, Akihiro. "Structure–activity relationships of vanillic acid ester analogs in inhibitory effect of antigen-mediated degranulation in rat basophilic leukemia RBL-2H3 cells". supporting information. p. 3533 - 3536. Retrieved 2016/07/22.