52744-26-0

Basic information

• Product Name: propyl 4-hydroxy-3-methoxyphenylacetate
• Synonyms: propyl 4-hydroxy-3-methoxyphenylacetate;4-Hydroxy-3-methoxybenzeneacetic acid propyl ester;Einecs 258-151-5;HoMovanillic Acid Propyl Ester;SYEBQVUZYCJAEQ-UHFFFAOYSA-N
• CAS NO: 52744-26-0
• Molecular Formula: C₁₂H₁₆O₄
• Molecular Weight: 224.25304
• EINECS: 258-151-5
• Product Categories: Aromatics, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 52744-26-0.mol

Chemical Properties

• Boiling Point: 336.5°C at 760 mmHg
• Flash Point: 124.4°C
• Appearance: /
• Density: 1.134g/cm³
• Vapor Pressure: 5.73E-05mmHg at 25°C
• Refractive Index: 1.519
• CAS DataBase Reference: propyl 4-hydroxy-3-methoxyphenylacetate(CAS DataBase Reference)
• NIST Chemistry Reference: propyl 4-hydroxy-3-methoxyphenylacetate(52744-26-0)
• EPA Substance Registry System: propyl 4-hydroxy-3-methoxyphenylacetate(52744-26-0)

Safety Data

• Hazardous Substances Data: 52744-26-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Propyl 4-hydroxy-3-methoxyphenylacetate is used as an intermediate in the synthesis of Sombrevin (S676765), which is an anesthetic agent. Its role in the synthesis process is crucial for the development of effective anesthetics that can provide pain relief during medical procedures.
Used in Anesthetic Applications:
Propyl 4-hydroxy-3-methoxyphenylacetate contributes to the development of anesthetic agents, such as Sombrevin, which are used for their pain-relieving properties during medical and surgical procedures. propyl 4-hydroxy-3-methoxyphenylacetate's involvement in the synthesis of these agents highlights its importance in the field of anesthesiology and patient care.

InChI:InChI=1/C12H16O4/c1-3-6-16-12(14)8-9-4-5-10(13)11(7-9)15-2/h4-5,7,13H,3,6,8H2,1-2H3

Upstream product

• 71-23-8 propan-1-ol 
• 306-08-1 Homovanillic acid 
• 90-05-1 2-methoxy-phenol 
• 55-10-7 4-hydroxy-3-methoxy-mandelic acid 

Downstream Products

• 1421-14-3 propanidid 

Relevant articles and documents

Design, synthesis, and evaluation of phenylpiperazine-phenylacetate derivatives as rapid recovery hypnotic agents

In this paper, we designed and synthesized a series of novel phenylpiperazine-phenylacetate derivatives as rapid recovery hypnotic agents. The best compound 10 had relatively high affinity for the GABAA receptor and low affinity for thirteen other off-target receptors. In three animal models (mice, rats, and rabbits), compound 10 exerted potent hypnotic effects (HD50 = 5.2 mg/kg in rabbits), comparable duration of the loss of righting reflex (LORR), and significant shorter recovery time (time to walk) than propanidid. Furthermore, compound 10 (TI = 18.1) showed higher safety profile than propanidid (TI = 14.7) in rabbits. Above results suggested that compound 10 may have predictable and rapid recovery profile in anesthesia.

Biological evaluation of natural and synthesized homovanillic acid esters as inhibitors of intestinal fatty acid uptake in differentiated Caco-2 cells

With raising prevalence of obesity, the regulation of human body fat is increasingly relevant. The modulation of fatty acid uptake by enterocytes represents a promising target for body weight maintenance. Recent results demonstrated that the trigeminal active compounds capsaicin, nonivamide, and trans-pellitorine dose-dependently reduce fatty acid uptake in differentiated Caco-2 cells as a model for the intestinal barrier. However, non-pungent alternatives have not been investigated and structural determinants for the modulation of intestinal fatty acid uptake have not been identified so far. Thus, based on the previous results, we synthesized 23 homovanillic acid esters in addition to the naturally occurring capsiate and screened them for their potential to reduce intestinal fatty acid uptake using the fluorescent fatty acid analog Bodipy-C12 in differentiated Caco-2 cells as an enterocyte model. Whereas pre-incubation with 100 μM capsiate did not change fatty acid uptake by Caco-2 enterocytes, a maximum inhibition of ?47% was reached using 100 μM 1-methylpentyl-2-(4-hydroxy-3-methoxy-phenyl)acetate. Structural analysis of the 24 structural analogues tested in the present study revealed that a branched fatty acid side chain, independent of the chain length, is one of the most important structural motifs associated with inhibition of fatty acid uptake in Caco-2 enterocytes. The results of the present study may serve as an important basis for designing potent dietary inhibitors of fatty acid uptake.

HOMOVANILLIC ESTER, MORE PARTICULARLY FOR ACHIEVING AN IMPRESSION OF HEAT AND/OR SPICINESS

Compounds of formula (I) and novel uses of compounds of formula (I), such as for flavour compositions. New preparations and new methods using compounds of formula (I).

Structure–activity relationships of vanillic acid ester analogs in inhibitory effect of antigen-mediated degranulation in rat basophilic leukemia RBL-2H3 cells

Methyl vanillate (1) showed strong degranulation inhibitory activity among vanillin derivatives tested. In order to find structure–activity relationships for developing anti-allergic agents with simple structures and potent activity, we synthesized several vanillic acid (VA) ester derivatives with C1–C4and C8alkyl chains and evaluated their degranulation inhibitory activities. The most active compound of VA ester derivatives was derivative 5 with a C4straight alkyl chain, and derivative 5 exhibited approximately three-fold greater inhibitory activity than that of 1. Moreover, we designed 8 types of analogs based on 5, and we found that the minimum structure for potent degranulation inhibitory activity requires direct connection of the butyl ester moiety on the benzene ring and at least one hydroxyl group on the benzene ring. Butyl meta or para hydroxyl benzoate (10 or 11) has a simpler structure than that of 5 and exhibited more potent degranulation inhibitory activity than that of 5.

Short-acting sedative hypnotic agents for anesthesia and sedation

The invention provides compounds compositions and methods useful for inducing or maintaining general anesthesia or sedation in mammals.