Isoamyl formate

Isoamyl formate^[1]^[2]

Names
Preferred IUPAC name 3-Methylbutyl formate
Systematic IUPAC name 3-Methylbutyl formate
Other names Isopentyl formate Isopentyl methanoate Isoamyl formate
Identifiers
CAS Number	110-45-2^Y
3D model (JSmol)	Interactive image
Beilstein Reference	1739893
ChEBI	CHEBI:31726^Y
ChEMBL	ChEMBL42013^Y
ChemSpider	7761^Y
ECHA InfoCard	100.003.428
EC Number	203-769-2
KEGG	C12293^Y
PubChem CID	8052
UNII	50L53EN043^Y
CompTox Dashboard (EPA)	DTXSID00861734
InChI InChI=1S/C6H12O2/c1-6(2)3-4-8-5-7/h5-6H,3-4H2,1-2H3 Key: XKYICAQFSCFURC-UHFFFAOYSA-N
SMILES CC(C)CCOC=O
Properties
Chemical formula	C6H12O2
Molar mass	116.160 g·mol^−1
Appearance	Colorless liquid
Odor	fruity (plum, blackcurrant)
Density	0.881−0.889 g/cm^3
Melting point	−93.5 °C (−136.3 °F; 179.7 K)
Boiling point	123.00 to 124.00 °C (253.40 to 255.20 °F; 396.15 to 397.15 K)
Solubility in water	3.5 g/L at 25 °C
Solubility	soluble in ethanol, most fixed oils and propylene glycol; insoluble in glycerol
Vapor pressure	9.97 mmHg (20 °C) 13.4 mmHg (25 °C)
Refractive index (nD)	1.396−1.400
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H319, H335
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264+P265, P271, P280, P303+P361+P353, P304+P340, P305+P351+P338, P319, P337+P317, P370+P378, P403+P233, P403+P235, P405, P501
Flash point	27 °C[3]
Lethal dose or concentration (LD, LC):
LD50 (median dose)	9840 mg/kg (oral, rat) 3020 mg/kg (oral, rabbit) >5 g/kg (dermal, rabbit)
Related compounds
Related compounds	Isoamyl acetate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Isoamyl formate, also known as isopentyl formate, is an ester formed from isoamyl alcohol and formic acid, with the formula C₆H₁₂O₂. It is a colorless liquid with a fruity odor of plum or blackcurrant.

Natural occurrence

Isoamyl formate is found in nature in the plant Plectranthus glabratus.^[1] It occurs in the following foods and drinks: avocado, beer, cheese, grape brandy, honey, pineapple, Mangifera (a plant genus including mangos), plum, quince, cider, rum, sea buckthorn, strawberry, tea, tequila, vinegar, and wine.^[3]

Preparation

Isoamyl formate may be prepared by the Fischer esterification of isoamyl alcohol and formic acid. Fischer esterifications of formic acid use an excess of formic acid as the solvent, and formic acid is a strong enough acid to self-catalyze the reaction without any other acid catalyst added.^[4]

Uses

Isoamyl formate is used as an aroma compound and artificial flavoring, for its odor of plum or blackcurrant.^[3][5]

Safety

Isoamyl formate has not been shown to be mutagenic or genotoxic in tests such as the Ames test.^[3]

References

1. "Isopentyl formate". PubChem. 10 February 2024. Retrieved 13 February 2024.
2. "NT0185000". ChemSpider. Retrieved 13 February 2024.
3. Api, A.M.; Belsito, D.; Botelho, D.; Browne, D.; Bruze, M.; Burton Jr., G.A.; Buschmann, J.; Calow, P.; Dagli, M.L.; Date, M.; Dekant, W.; Deodhar, C; Fryer, A.D.; Joshi, K.; La Cava, S.; Lapczynsky, A.; Lieblier, D.C.; O'Brien, D.; Parakhia, R.; Patel, A.; Penning, T.M.; Ritacco, G.; Romine, J.; Salvito, D.; Schultz, T.W.; Sipes, I.G.; Thakkar, Y.; Tsang, S.; Wahler, J. (2017). "RIFM fragrance ingredient safety assessment, isoamyl formate, CAS Registry Number 110-45-2". Food and Chemical Toxicology. 110: S142 – S150. doi:10.1016/j.fct.2017.04.013. PMID 28419849.
4. Furniss, Brian S.; Hannaford, Antony, J.; Smith, Peter W. G.; Tatchell, Austin S. (1989). Vogel's Textbook of Practical Organic Chemistry (5th ed.). Longman Scientific & Technical. pp. 696, 701. ISBN 978-0582462366.
5. "isoamyl formate". The Good Scents Company. Archived from the original on 22 July 2023.