Methyl hexanoate

Methyl hexanoate is the fatty acid methyl ester of hexanoic acid (caproic acid), a colourless liquid organic compound with the chemical formula CH₃−(CH₂)₄−COO−CH₃. It is found naturally in many foods and has a role as a plant metabolite. It can also be found in the cytoplasm of cells.^[1]

Methyl hexanoate

Names
Preferred IUPAC name Methyl hexanoate
Other names Methyl caproate Methyl hexanate
Identifiers
CAS Number	106-70-7
3D model (JSmol)	Interactive image
Beilstein Reference	1744683
ChEBI	CHEBI:77322
ECHA InfoCard	100.003.115
EC Number	203-425-1
PubChem CID	7824
UNII	246364VPJS
UN number	1993
CompTox Dashboard (EPA)	DTXSID0047616
InChI InChI=1S/C7H14O2/c1-3-4-5-6-7(8)9-2/h3-6H2,1-2H3 Key: NUKZAGXMHTUAFE-UHFFFAOYSA-N
SMILES CCCCCC(=O)OC
Properties[1]
Chemical formula	C7H14O2
Molar mass	130.187 g·mol−1
Density	0.8846
Melting point	−71.0 °C (−95.8 °F; 202.2 K)
Boiling point	149.5 °C (301.1 °F; 422.6 K)
Solubility in water	1.33 mg/mL at 20 °C
Solubility	ethanol
Refractive index (nD)	1.4049
Related compounds
Related compounds	Ethyl hexanoate, Propyl hexanoate, Butyl hexanoate Allyl hexanoate
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226
Precautionary statements	P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, P501
Flash point	73 °C; 163 °F; 346 K
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Methyl hexanoate is produced industrially for use as a flavouring agent.^[2][3] It can also be used as fragrance for a pineapple smell.^[4]

Production

Methyl hexanoate is produced in multi-tonne quantities for use as a flavouring agent.^[3] It is made by combining methanol with hexanoic acid.^{[citation needed]}

Uses

Methyl hexanoate is found naturally in foods like potatoes, tomatoes and cheese and is a constituent of some alcoholic beverages.^[2] It can be used to mimic the flavor of pineapple like its related ester ethyl hexanoate.^[4]

Safety

The LD₅₀ for rats is more than 5 g/kg,^[1] indicating low toxicity. When heated to decomposition, methyl hexanoate emits toxic fumes. It can cause burns.

Flammability

Methyl hexanoate is flammable. It has a flash point of 163 °F (73 °C).^[1]

See also

• Ethyl hexanoate
• Propyl hexanoate

References

1. "Methyl hexanoate". PubChem. Retrieved 12 August 2020.
2. Maarse, Henk (29 March 1991). Volatile Compounds in Foods and Beverages. ISBN 978-0824783907.
3. "Methyl hexanoate – Substance Information". European Chemicals Agency. Retrieved 12 August 2020.
4. "Methyl hexanoate". The Good Scents Company. Retrieved 15 August 2020.