Ethyl decadienoate

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

Ethyl decadienoate
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
ECHA InfoCard 100.019.254
UNII
  • InChI=1S/C12H20O2/c1-3-5-6-7-8-9-10-11-12(13)14-4-2/h8-11H,3-7H2,1-2H3/b9-8-,11-10+
    Key: OPCRGEVPIBLWAY-QNRZBPGKSA-N
  • InChI=1/C12H20O2/c1-3-5-6-7-8-9-10-11-12(13)14-4-2/h8-11H,3-7H2,1-2H3/b9-8-,11-10+
    Key: OPCRGEVPIBLWAY-QNRZBPGKBN
  • O=C(OCC)\C=C\C=C/CCCCC
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

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. Michael Zviely (August 23, 2011). "Pear Ester: Ethyl (E,Z)-2,4-decadienoate". Perfumer & Flavorist.
  2. "Ethyl 2-trans-4-cis-decadienoate". Sigma-Aldrich.
  3. 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. S. Tsuboi, T. Masuda, S. Mimura, and A. Takeda (1988). "Ethyl (E,Z)-2,4-Decadienoate". Organic Syntheses. 66: 22.{{cite journal}}: CS1 maint: multiple names: authors list (link); Collective Volume, vol. 8, p. 251
  5. "Ethyl (E,Z)-2,4-decadienoate". Good Scents Company.
  6. "ETHYL DECADIENOATE, NATURAL". natural-advantage.net.
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