Pelargonic acid methyl ester

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Structural formula
Structural formula of pelargonic acid methyl ester
General
Surname Pelargonic acid methyl ester
other names
  • Methyl nonanoate ( IUPAC )
  • Methyl pelargonate
  • Nonanoic acid methyl ester
  • METHYL PELARGONATE ( INCI )
Molecular formula C 10 H 20 O 2
Brief description

colorless liquid

External identifiers / databases
CAS number 1731-84-6
EC number 217-052-7
ECHA InfoCard 100.015.502
PubChem 15606
ChemSpider 14846
DrugBank DB01631
Wikidata Q3343334
properties
Molar mass 172.27 g mol −1
Physical state

liquid

density

0.875 g cm −3

Melting point

−30 ° C

boiling point

213 ° C

Vapor pressure

0.1 hPa (20 ° C)

solubility
Refractive index

1.421 (20 ° C)

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Pelargonic acid methyl ester is a fruit flavor and a chemical compound from the group of carboxylic acid esters .

Occurrence

Pelargonic acid methyl ester was found in Orris derivatives, apples , bananas , blackberries , baked potatoes, blue cheese , beef fat, hop oil , white wine , star fruit , prickly pears , bourbon vanilla, mountain papaya, monkey orange and rooibos tea ( Aspalathus linearis ).

  • Apple

  • banana

  • blackberry

  • Blue cheese

Extraction and presentation

Pelargonic acid methyl ester can be obtained industrially by acid-catalyzed esterification of pelargonic acid with methanol at temperatures of 30-60 ° C in the presence of acidic cation exchangers based on a sulfonated styrene-divinylbenzene copolymer and subsequent rectification .

Acid-catalyzed esterification of nonanoic acid with methanol to give methyl nonanoate and water in the presence of an acidic cation exchange resin

Another possibility is the catalytic hydrogenation of 1,5-octadienecarboxylic acid methyl ester using palladium (II) chloride in methanol as solvent.

properties

Pelargonic acid methyl ester is a flammable, difficult to ignite, colorless liquid that is practically insoluble in water. The compound has a wine-like and coconut-like odor. Below 10 ppm it has a sweet, coconut-like taste.

use

Pelargonic acid methyl ester for the synthesis of vanillyl nonanoate , a model compound of capsinoids , and used as a flavoring substance .

safety instructions

The vapors of pelargonic acid methyl ester can form an explosive mixture with air ( flash point 87 ° C).

Individual evidence

  1. ↑ Entry on METHYL PELARGONATE in the CosIng database of the EU Commission, accessed on July 6, 2020.
  2. ↑ a b c d e f g h i j k Entry on pelargonic acid methyl ester in the GESTIS substance database of the IFA , accessed on December 14, 2018(JavaScript required) .
  3. ↑ a b c d e George A. Burdock: Fenaroli's Handbook of Flavor Ingredients . CRC Press, 2004, ISBN 978-1-4200-3787-6 , pp. 1240 ( limited preview in Google Book search).
  4. ↑ a b Data sheet Methyl nonanoate, 98% from Sigma-Aldrich , accessed on December 14, 2018 ( PDF ).
  5. ↑ Mamta Sharma, Ravinder Kumar Wanchoo, Amrit Pal Toor: Adsorption and Kinetic Parameters for Synthesis of Methyl Nonanoate over Heterogeneous Catalysts. In: Ind. Eng. Chem. Res. 2012, 51, 44, 14367-14375, ACS Publications , October 2, 2012, doi : 10.1021 / ie301661n .