6290-37-5

Basic information

• Product Name: FEMA 3221
• Synonyms: 2-Phenethyl hexanoate;2-Phenylethylhexanoate;Hexanoic acid, 2-phenylethyl ester;Hexanoic acid, phenethyl ester;Hexanoicacid,2-phenylethylester;Hexanoicacid,phenethylester;Phenylethyl n-hexanoate;FEMA 3221
• CAS NO: 6290-37-5
• Molecular Formula: C₁₄H₂₀O₂
• Molecular Weight: 220.31
• EINECS: 228-538-3
• Mol File: 6290-37-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 304.5°Cat760mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 0.971 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000869mmHg at 25°C
• Refractive Index: n20/D 1.486(lit.)
• CAS DataBase Reference: FEMA 3221(CAS DataBase Reference)
• NIST Chemistry Reference: FEMA 3221(6290-37-5)
• EPA Substance Registry System: FEMA 3221(6290-37-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 6290-37-5(Hazardous Substances Data)

Usage

Chemical Properties

Phenethyl hexanoate has a fresh, fruity green, rosy, fresh, banana-like odor reminiscent of pineapple and a pleasant taste

Occurrence

Reported found in Burley tobacco, yellow passion fruit, blue cheese, beer, cognac, malt whiskey, cider, sherry, white wine, red wine, botrytised wine, rum, apple brandy, grape brandy, lamb’s lettuce and sea buckthorn.

Aroma threshold values

Aroma characteristics at 1.0%: sharp, winey, cocoa, honey, vanilla, yeasty, floral with hints of jamy fruity nuances.

Taste threshold values

Taste characteristics at 10 ppm: cocoa, fruity, green, winey, fermented and slightly astringent.

InChI:InChI=1/C14H20O2/c1-2-3-5-10-14(15)16-12-11-13-8-6-4-7-9-13/h4,6-9H,2-3,5,10-12H2,1H3

Upstream product

• 60-12-8 2-phenylethanol 
• 111-27-3 hexan-1-ol 
• 142-62-1 hexanoic acid 
• 1074-16-4 2-bromophenylethyl alcohol 
• 616-05-7 2-bromohexanoic acid 
• 93-54-9 1-Phenyl-1-propanol 
• 142-61-0 Hexanoyl chloride 
• 2051-49-2 n-hexanoic anhydride 

Downstream Products

• 60-12-8 2-phenylethanol 
• 111-27-3 hexan-1-ol 

Relevant articles and documents

Further evidence of extensive pulmonary first-pass ester hydrolysis after airways administration in rats

The aim of this study was to synthesize an ester with low lipophilicity, and to use this ester to further investigate pre-absorptive pulmonary first-pass metabolism. Hexanoic acid phenethyl ester was synthesized by reacting 2-phenylethanol with hexanoyl chloride. Pre-absorptive first-pass metabolism was assessed by comparing the areas under the blood concentration-time curves after intra-arterial administration of the hexanoic acid phenethyl ester with those after intratracheal instillation. Hexanoic acid phenethyl ester experienced extensive first-pass metabolism (53% of the absorbed dose) before or during absorption. This and earlier data suggests that the extent of this first-pass extraction is dependent on the physicochemical properties of the ester and in particular whether a compound experiences diffusion-limited absorption. Pre-absorptive pulmonary first-pass metabolism of compounds whose absorption iS diffusion-rate limited may be extensive even when pulmonary enzyme expression is low. This has consequences for the systemic delivery of drugs and in particular esters via the lungs.

Transfer Hydro-dehalogenation of Organic Halides Catalyzed by Ruthenium(II) Complex

A simple and efficient Ru(II)-catalyzed transfer hydro-dehalogenation of organic halides using 2-propanol solvent as the hydride source was reported. This methodology is applicable for hydro-dehalogenation of a variety of aromatic halides and α-haloesters and amides without additional ligand, and quantitative yields were achieved in many cases. The potential synthetic application of this method was demonstrated by efficient gram-scale transformation with catalyst loading as low as 0.5 mol %.

Recyclable hypervalent iodine(III) reagent iodosodilactone as an efficient coupling reagent for direct esterification, amidation, and peptide coupling

A hypervalent iodine(III) reagent plays a novel role as an efficient coupling reagent to promote the direct condensation between carboxylic acids and alcohols or amines to provide esters, macrocyclic lactones, amides, as well as peptides without racemization. The regeneration of iodosodilactone (1) can also be readily achieved. The intermediate acyloxyphosphonium ion C from the activation of a carboxylic acid is thought to be involved in the present esterification reaction.