| |
| |
| |
| Names | |
|---|---|
| Preferred IUPAC name 3-Methylbutyl formate | |
| Systematic IUPAC name 3-Methylbutyl formate | |
| Other names
Isopentyl formate Isopentyl methanoate Isoamyl formate | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| Beilstein Reference | 1739893 |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.003.428 
|
| EC Number |
|
| KEGG | |
| PubChem CID | |
| UNII | |
| CompTox Dashboard (EPA) | |
InChI
| |
SMILES
| |
| Properties | |
| Chemical formula | C6H12O2 |
| Molar mass | 116.160 g·mol |
| Appearance | Colorless liquid |
| Odor | fruity (plum, blackcurrant) |
| Density | 0.881−0.889 g/cm |
| 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 |
| Lethal dose or concentration (LD, LC): | |
| LD50 (median dose) |
|
| Related compounds | |
| Related compounds | Isoamyl acetate |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 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. 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.
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.
Uses
Isoamyl formate is used as an aroma compound and artificial flavoring, for its odor of plum or blackcurrant.
Safety
Isoamyl formate has not been shown to be mutagenic or genotoxic in tests such as the Ames test.
References
- ^ "Isopentyl formate". PubChem. 10 February 2024. Retrieved 13 February 2024.
- "NT0185000". ChemSpider. Retrieved 13 February 2024.
- ^ 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.
- 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.
{{cite book}}: CS1 maint: multiple names: authors list (link) - "isoamyl formate". The Good Scents Company. Archived from the original on 22 July 2023.
| Esters | |
|---|---|
| Methyl esters | |
| Ethyl esters | |
| Propyl esters | |
| Butyl esters | |
| Amyl esters | |
| Hexyl esters | |
| Phenyl esters | |
| Heptyl esters | |
| Benzyl esters | |