Ethyl decadienoate

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
CAS Number	3025-30-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:4896;
ChemSpider	4444602;
ECHA InfoCard	100.019.254
PubChem CID	5281162;
UNII	79P6KS9Y5Z ;
CompTox Dashboard (EPA)	DTXSID0041357 ;
	InChI 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;
	SMILES O=C(OCC)\C=C\C=C/CCCCC;
Properties
Chemical formula	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];
Solubility in water	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]

gollark: Yes.

gollark: That seems about right.

gollark: Lower frequencies become *less* dominant?

gollark: Just put in the temperature of the sun and a red dwarf, and see which one has the most area under the line around the infrared bits.

gollark: Yep.

References

Michael Zviely (August 23, 2011). "Pear Ester: Ethyl (E,Z)-2,4-decadienoate". Perfumer & Flavorist.
"Ethyl 2-trans-4-cis-decadienoate". Sigma-Aldrich.
Alexakis, A.; Cahiez, G.; Normant, J.F. (1980). "Vinyl-copper derivatives—XI". Tetrahedron. 36 (13): 1961. doi:10.1016/0040-4020(80)80209-2.
S. Tsuboi, T. Masuda, S. Mimura, and A. Takeda (1988). "Ethyl (E,Z)-2,4-Decadienoate". Organic Syntheses. 66: 22.CS1 maint: multiple names: authors list (link); Collective Volume, 8, p. 251
"Ethyl (E,Z)-2,4-decadienoate". Good Scents Company.
"ETHYL DECADIENOATE, NATURAL". natural-advantage.net.

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[PF-1] Michael Zviely (August 23, 2011). "Pear Ester: Ethyl (E,Z)-2,4-decadienoate". Perfumer & Flavorist.

[SA-2] "Ethyl 2-trans-4-cis-decadienoate". Sigma-Aldrich.

[Alexakis-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.

[OrgSynth-4] S. Tsuboi, T. Masuda, S. Mimura, and A. Takeda (1988). "Ethyl (E,Z)-2,4-Decadienoate". Organic Syntheses. 66: 22.CS1 maint: multiple names: authors list (link); Collective Volume, 8, p. 251

[5] "Ethyl (E,Z)-2,4-decadienoate". Good Scents Company.

[6] "ETHYL DECADIENOATE, NATURAL". natural-advantage.net.