110599-11-6

Basic information

• Product Name: 2-(2-hydroxyethoxy)ethyl 2-(6-methoxynaphthalen-2-yl)propanoate
• CAS NO: 110599-11-6
• Molecular Formula: C₁₈H₂₂O₅
• Molecular Weight: 318.3643
• Mol File: 110599-11-6.mol

Chemical Properties

• Boiling Point: 481.5°C at 760 mmHg
• Flash Point: 171.1°C
• Density: 1.174g/cm³
• Vapor Pressure: 4.41E-10mmHg at 25°C
• Refractive Index: 1.567
• CAS DataBase Reference: 2-(2-hydroxyethoxy)ethyl 2-(6-methoxynaphthalen-2-yl)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-hydroxyethoxy)ethyl 2-(6-methoxynaphthalen-2-yl)propanoate(110599-11-6)
• EPA Substance Registry System: 2-(2-hydroxyethoxy)ethyl 2-(6-methoxynaphthalen-2-yl)propanoate(110599-11-6)

Safety Data

• Hazardous Substances Data: 110599-11-6(Hazardous Substances Data)

Usage

Physical State

Clear liquid

Odor

Mild floral

Primary Use

Absorbing UVB rays in sunscreens to protect skin from sun damage

Safety

Considered safe for use in cosmetics and personal care products when used within concentration limits set by regulatory authorities

Potential Concern

Possible disruption of hormone regulation in the body

Regulation

Use is regulated in some regions due to potential hormone-disrupting properties

Upstream product

• 51091-84-0 (S)-naproxenoyl chloride 
• 111-46-6 diethylene glycol 
• 22204-53-1 (2S)-2-(6-methoxy(2-naphthyl))propanoic acid 

Relevant articles and documents

Esters of naproxen as prodrugs for skin penetration, I: Synthesis and physico-chemical properties

Several esters of the nonsteroidal antiinflammatory drug Naproxen [2-(6-methoxy-2-naphthyl)propionic acid] were synthesized by standard procedures. Melting points and enthalpies of melting were obtained by differential scanning calorimetry. Solubilities in water were measured using HPLC. The partition coefficients (octanol/water) were calculated according to Rekker and Mannhold and Rm-values were determined by RP-TLC. The two latter parameters were correlated with high significance.

In vitro and in vivo evaluation of polyoxyethylene esters as dermal prodrugs of ketoprofen, naproxen and diclofenac

Novel polyoxyethylene esters of ketoprofen (1a-e), naproxen (2a-e) and diclofenac (3a-e) were synthesized and evaluated as potential dermal prodrugs of naproxen, ketoprofen and diclofenac. These esters were obtained by coupling these drugs with polyoxyethylene glycols by a succinic acid spacer. The aqueous solubilities, lipophilicities and hydrolysis rates of esters 1a-e, 2a-e and 3a-e were determined in a buffered solution and in porcine esterase. The permeation of these prodrugs through excised human skin was studied in vitro. Furthermore we investigated the in vivo topical anti-inflammatory activity of esters 1d, 2e and 3e, which showed the best in vitro profile, evaluating the ability of these compounds to inhibit methyl nicotinate (MN)-induced skin erythema on healthy human volunteers. Esters 1a-e, 2a-e and 3a-e showed good water stability and rapid enzymatic cleavage and their hydrolysis rates, both chemical and enzymatic, were not significantly affected by the length of the polyoxyethylenic chain used as promoiety. Concerning in vitro percutaneous absorption studies, only esters 1d-e, 2d-e and 3c-e showed an increased flux through stratum corneum and epidermis membranes compared to their respective parent drugs. In vivo results showed an interesting delayed and sustained activity of esters 1d and 3e compared to the parent drugs. In conclusion polyoxyethylene glycols could prove to be suitable promoieties for ketoprofen, naproxen and diclofenac design since esters 1d-e, 2d-e and 3c-e showed some requirements (chemical stability, enzymatic lability and an increased skin permeation) needed to obtain successful dermal prodrugs. Furthermore, was observed an appreciable and sustained in vivo topical anti-inflammatory activity of esters 1d and 3e, compared to the parent drugs, using MN-induced erythema in human volunteers as inflammation model. Copyright