Chemistry:Ethyl decadienoate

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Ethyl decadienoate
Ethyl decadienoate.svg
Names
Preferred IUPAC name
Ethyl (2E,4Z)-deca-2,4-dienoate
Other names
Ethyl (2E,4Z)-2,4-decadienoate
Pear ester
Ethyl 2-trans-4-cis-decadienoate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
Properties
C12H20O2
Molar mass 196.290 g·mol−1
Appearance Colorless liquid[1]
Boiling point 70–72 °C (158–162 °F; 343–345 K)
  • (0.05 mmHg)[2]
  • 81–82 °C (178–180 °F) (0.1 mmHg)[3]
  • 83–88 °C (181–190 °F) (0.1 mmHg)[4]
8.588 mg/L (est.)[5]
Hazards
Flash point 113 °C (235 °F)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Ethyl decadienoate, also known as pear ester, is an organic chemical compound used in flavors and perfumery for its pear-like taste and odor.

Occurrence and preparation

Ethyl decadienoate is found in apples, Bartlett pears, Concord grapes, beer, pear brandy and quince.[1]

It can also be prepared synthetically from 1-octyn-3-ol[4] or from ethyl propiolate.[3]

Uses

Ethyl decadienoate is used in natural flavors and fragrances for its intense fruity flavor. In the United States, as a food additive it is listed as generally recognized as safe (GRAS).[6]

References

  1. 1.0 1.1 Michael Zviely (August 23, 2011). "Pear Ester: Ethyl (E,Z)-2,4-decadienoate". Perfumer & Flavorist. http://www.perfumerflavorist.com/fragrance/rawmaterials/natural/128267048.html. 
  2. 2.0 2.1 "Ethyl 2-trans-4-cis-decadienoate". Sigma-Aldrich. http://www.sigmaaldrich.com/catalog/product/ALDRICH/W314811?lang=en. 
  3. 3.0 3.1 Alexakis, A.; Cahiez, G.; Normant, J.F. (1980). "Vinyl-copper derivatives—XI". Tetrahedron 36 (13): 1961. doi:10.1016/0040-4020(80)80209-2. 
  4. 4.0 4.1 S. Tsuboi, T. Masuda, S. Mimura, and A. Takeda (1988). "Ethyl (E,Z)-2,4-Decadienoate". Organic Syntheses 66: 22. http://www.orgsyn.org/demo.aspx?prep=cv8p0251. ; Collective Volume, 8, pp. 251 
  5. "Ethyl (E,Z)-2,4-decadienoate". Good Scents Company. http://www.thegoodscentscompany.com/data/rw1029341.html. 
  6. "ETHYL DECADIENOATE, NATURAL". natural-advantage.net. http://www.natural-advantage.net/Et-Deca.htm.