Cinnamon acetate

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of (E) -acetic acid cinnamon ester

Structural formula of (Z) -acetic acid cinnamon ester
( E ) -isomer (top) and ( Z ) -isomer
General
Surname Cinnamon acetate
other names
  • Cinnamyl acetate
  • Cinnamyl acetate
  • 3-phenylprop-2-enyl acetate
  • CINNAMYL ACETATE ( INCI )
Molecular formula C 11 H 12 O 2
Brief description

colorless liquid

External identifiers / databases
CAS number
  • 103-54-8
  • 21040-45-9 [( E ) -form]
  • 77134-01-1 [( Z ) form]
EC number 203-121-9
ECHA InfoCard 100,002,838
PubChem 7660
ChemSpider 7377
Wikidata Q61734302
properties
Molar mass 176.21 g mol −1
Physical state

liquid

density

1.057 g cm −3 (25 ° C)

boiling point

265 ° C

solubility
  • soluble in ethanol
  • practically insoluble in water
  • soluble in most organic solvents
Refractive index

1.541 (20 ° C)

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 319
P: 305 + 351 + 338
Toxicological data

3300 mg kg −1 ( LD 50 ,  rat ,  oral )

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

Cinnamon ester is a chemical compound from the ester group , more precisely the cinnamon ester. The compound occurs in two isomeric forms.

Occurrence

Star fruit ( Averrhoa carambola )

Cinnamon ester is found naturally in Chinese cinnamon , melon , star fruit , tarragon , lychee, and others. The ( E ) form dominates in cinnamon . The ( Z ) -form occurs in higher quantities in the leaves.

Extraction and presentation

Cinnamon acetate ( 2 ) can be synthesized by the lipase-catalyzed transesterification of cinnamon alcohol ( 1 ) with vinyl acetate in a non-aqueous medium:

Biosynthesis of cinnamon acetate

From 1 and ethyl acetate, 2 can also be obtained by transesterification under the catalytic effect of Novozyl 435 :

Biosynthesis of cinnamon acetate

The esterification of cinnamon alcohol with acetic acid also gives 2 .

Cinnamon ester ( 2 ) can also be synthesized from cinnamyl bromide ( 3 ) and sodium acetate in a batch reactor using quaternary ammonium bromide as a phase transfer catalyst (PTC) in a solid-liquid reaction mode:

Phase transfer catalyzed synthesis of cinnamon ester

Furthermore, 2 can also be obtained biotechnologically.

properties

Cinnamon acetate is a colorless liquid that is soluble in ethanol . It has a characteristic balsamic-floral odor and a burning, sweet taste that is reminiscent of pineapple .

use

Cinnamon acetate is used as a flavoring and odorant. It is used as a fixator in perfumery and as a fragrance component for oriental notes. In terms of aromas, it is used to create fruity, cinnamon-like notes.

Web links

Commons : Cinnamon Acetate  - Collection of images, videos and audio files

Individual evidence

  1. ↑ Entry on CINNAMYL ACETATE in the CosIng database of the EU Commission, accessed on May 17, 2020.
  2. ↑ a b c d e f g h i j data sheet Cinnamyl acetate, 99% from Sigma-Aldrich , accessed on October 12, 2018 ( PDF ).
  3. ↑ a b c d e George A. Burdock: Encyclopedia of Food and Color Additives . CRC Press, 1997, ISBN 978-0-8493-9412-6 , pp. 2996 ( limited preview in Google Book search).
  4. ↑ J. SCHORMÜLLER: Alkaloid- containing luxury foods, spices, table salt . Springer-Verlag, 2013, ISBN 978-3-642-46225-2 , p. 461 ( limited preview in Google Book search).
  5. ↑ George A. Burdock: Fenaroli's Handbook of Flavor Ingredients . CRC Press, 2016, ISBN 978-1-4200-9086-4 , pp. 2037 ( limited preview in Google Book search).
  6. ↑ VA Parthasarathy, Bhageerathy Chempakam, T. John Zachariah: Chemistry of Spices . CABI, 2008, ISBN 978-1-84593-420-0 , pp. 126, 128 ( limited preview in Google Book search).
  7. ↑ a b Ganapati D. Yadav, Saravanan Devendran: Lipase catalyzed synthesis of cinnamyl acetate via transesterification in non-aqueous medium. In: Process Biochemistry. 47, 2012, p. 496, doi : 10.1016 / j.procbio.2011.12.008 .
  8. ↑ Cinnamyl acetate data sheet from ELAN CHEMICAL COMPANY, INC, November 30, 2005.
  9. ↑ Venu Gopal Devulapelli, Hung-Shan Weng: Synthesis of cinnamyl acetate by solid-liquid phase transfer catalysis: Kinetic study with a batch reactor. In: Catalysis Communications. 10, 2009, p. 1638, doi : 10.1016 / j.catcom.2009.04.032 .
  10. ↑ Hao Dong, Francesco Secundo, Changhu Xue, Xiangzhao Mao: Whole-Cell Biocatalytic Synthesis of Cinnamyl Acetate with a Novel Esterase from the DNA Library of Acinetobacter hemolyticus. In: Journal of Agricultural and Food Chemistry. 65, 2017, p. 2120, doi : 10.1021 / acs.jafc.6b05799 .
  11. ↑ Entry on cinnamyl acetate. In: Römpp Online . Georg Thieme Verlag, accessed on October 13, 2018.