31501-11-8

Basic information

• Product Name: cis-3-Hexenyl hexanoate
• Synonyms: CIS-HEX-3-ENYL HEXANOATE;CIS-3-HEXENYL HEXANOATE;CIS-3-HEXENYL CAPROATE;CIS-3-HEXEN-1-YL N-HEXANOATE;HEXENYL-CIS-3-CAPROATE;HEXENYL-CIS-3-HEXANOATE;FEMA 3403;C3 HEXENYL CAPROATE
• CAS NO: 31501-11-8
• Molecular Formula: C₁₂H₂₂O₂
• Molecular Weight: 198.3
• EINECS: 250-661-6
• Product Categories: Alphabetical Listings;Flavors and Fragrances;G-H
• Mol File: 31501-11-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 17.88°C (estimate)
• Boiling Point: 115 °C15 mm Hg(lit.)
• Flash Point: 220 °F
• Appearance: /
• Density: 0.88 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0156mmHg at 25°C
• Refractive Index: n20/D 1.473(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: cis-3-Hexenyl hexanoate(CAS DataBase Reference)
• NIST Chemistry Reference: cis-3-Hexenyl hexanoate(31501-11-8)
• EPA Substance Registry System: cis-3-Hexenyl hexanoate(31501-11-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: MO8380000
• Hazardous Substances Data: 31501-11-8(Hazardous Substances Data)

Usage

Description

cis-3-Hexenyl hexanoate has a powerful, diffusive fruity-green odor.1 It is reminiscent of pear. May be synthesized by azeotropic esterification of ds-3-hexanol with n-hexanoic acid.

Chemical Properties

cis-3-Hexenyl hexanoate has a powerful, diffusive fruity-green odor, reminiscent of pear.

Occurrence

Reported found among the high-boiling components in green tea; also as a component in the volatile fraction of tabasco pepper (Capsicum frutescens). Also reported found in orange peel oil, guava, corn mint oil, passion fruit and juice, plum, plumcot, starfruit, mango, quince, beli (Aegle marmelos Correa), babaco fruit (Carica pentagona Heilborn), nectarine and black choke berry

Preparation

By azeotropic esterification of cis-3-hexanol with n-hexanoic acid

Taste threshold values

Taste characteristics at 20 ppm: green, fruity, waxy and sweet with a berry and tropical nuance

InChI:InChI=1/C12H22O2/c1-3-5-7-9-11-14-12(13)10-8-6-4-2/h5,7H,3-4,6,8-11H2,1-2H3/b7-5-

Upstream product

• 928-96-1 (Z)-3-Hexen-1-ol 
• 626-82-4 butyl hexanoate 
• 142-62-1 hexanoic acid 

Downstream Products

• 626-82-4 butyl hexanoate 
• 6378-65-0 n-hexyl caproate 

Relevant articles and documents

Rape seedling lipase catalyzed synthesis of flavor esters through transesterification in hexane

Butyl butyrate, a short-chain ester with fruity pineapple odor, is a significant flavor compound that is widely used in the food industry. Enzymatic synthesis of butyl butyrate by crude rape seedlings lipase has been investigated in n-hexane using 50 g/L of enzyme at 40 °C through alcoholysis of ethyl butyrate with butanol. The influence of reaction parameters such aswater content, water activity, substrate concentrations and reaction time were also studied. Ester yield of 60% after 96 h has been obtained with 0.5% (v/v) of added water using reversible reaction or activated ester. A concentration of 0.1M of butanol while 0.6 M of ethyl butyrate was found optimal for butyl butyrate synthesis. The esterification catalyzed by lipase was inhibited by increasing the butanol concentration beyond 0.10 M while no inhibition of enzyme was observed with ethyl butyrate. (Z)-3-hexen-1-ol (cis-3-hexen-1-ol) esters posses the odour of freshly cut grass and are used to obtain natural green top notes in food flavours. Two different approaches for rapeseed lipase catalyzed synthesis of these flavour esters were also studied. Acylation of (Z)-3-hexen-1-ol with vinyl acetate (irreversible acyl donor) and butyl caproate (reversible acyl donor) was evaluated. Ester yield of 99 % after 24 h was obtained for (Z)-3-hexen-1-yl acetate with vinyl acetate as acyl donor. Crude rape seedlings lipase has proved to be an efficient catalyst to obtain (Z)-3-hexen-1-ol esters using irreversible acyl donor such as vinyl ester in hexane. Crude lipase also works well at ambient temperature without need of immobilization.