Ethyl decadienoate

Last updated
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
ECHA InfoCard 100.019.254 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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
AppearanceColorless 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).

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

Contents

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]

Related Research Articles

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tert-Butylthiol, also known as tert-butyl mercaptan (TBM), and abbreciated t-BuSH, is an organosulfur compound with the formula (CH3)3CSH. This thiol is used as an odorant for natural gas, which is otherwise odorless. It may also have been used as a flavoring agent.

Decadienoic acid is any mono-carboxylic acid with an unbranched chain of ten carbon atoms, connected by seven single bonds and two double bonds. That is, any compound with formula HO(O=)C–(CH
2
)
x
–CH=CH–(CH
2
)
y
–CH=CH–(–CH
2
)
z
–H where x, y, and z can be zero or more, and x+y+z = 5 ; or HO(O=)C–(CH
2
)
r
–CH=C=CH–(CH
2
)
s
–H where r + s = 6. All these compounds have the formula C
10
H
16
O
2
. A salt or ester of such an acid is called a decadienoate.

References

  1. 1 2 Michael Zviely (August 23, 2011). "Pear Ester: Ethyl (E,Z)-2,4-decadienoate". Perfumer & Flavorist.
  2. 1 2 "Ethyl 2-trans-4-cis-decadienoate". Sigma-Aldrich.
  3. 1 2 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. 1 2 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); Collected Volumes, vol. 8, p. 251.
  5. "Ethyl (E,Z)-2,4-decadienoate". Good Scents Company.
  6. "ETHYL DECADIENOATE, NATURAL". natural-advantage.net. Archived from the original on 2011-01-04. Retrieved 2012-09-27.