Allyl hexanoate

Allyl hexanoate is an organic compound with the formula C5H11CO2CH2CH=CH2. It is a colorless liquid, although commercial samples appear yellowish. It occurs naturally in pineapples.[3]

Allyl hexanoate
Names
Preferred IUPAC name
Prop-2-en-1-yl hexanoate
Other names
Prop-2-enyl hexanoate
Allyl hexanoate
Allyl caproate
Allyl n-caproate
2-Propenyl n-hexanoate
Hexanoic acid 2-propenyl ester
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.222
EC Number
  • 204-642-4
UNII
  • InChI=1S/C9H16O2/c1-3-5-6-7-9(10)11-8-4-2/h4H,2-3,5-8H2,1H3 checkY
    Key: RCSBILYQLVXLJG-UHFFFAOYSA-N checkY
  • InChI=1/C9H16O2/c1-3-5-6-7-9(10)11-8-4-2/h4H,2-3,5-8H2,1H3
    Key: RCSBILYQLVXLJG-UHFFFAOYAX
  • CCCCCC(OCC=C)=O
  • O=C(OCC=C)CCCCC
Properties
C9H16O2
Molar mass 156.225 g·mol−1
Appearance Colorless to pale yellow clear liquid[1]
Density 0.887 g/mL[2]
0.884-0.892 g/mL[1]
Boiling point 190 to 191 °C (374 to 376 °F; 463 to 464 K)[1]
75-76 °C (15 mmHg)[2]
Insoluble[1]
Hazards
GHS labelling:
GHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
Danger
H301, H311, H315, H319, H331, H410, H411, H412
P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P311, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P391, P403+P233, P405, P501
Flash point 66 °C (151 °F; 339 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Uses

Allyl hexanoate is employed principally in the formulation of pineapple flavors but it can also be used for peach and apricot essences and for apple blossom, peach blossom, and wisteria perfume compositions.[1] It is an ingredient of some lipstick perfumes and cigarette tobacco. It also adds a sweet juicy note to citrus flavors.

References
  1. Allyl hexanoate at The Good Scents Company
  2. Allyl caproate at Sigma-Aldrich
  3. Johannes Panten and Horst Surburg "Flavors and Fragrances, 2. Aliphatic Compounds" in Ullmann's Encyclopedia of Industrial Chemistry, 2015, Wiley-VCH, Weinheim.doi:10.1002/14356007.t11_t01
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