Chemistry:Isoamyl formate
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| Names | |
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| Preferred IUPAC name
3-Methylbutyl formate | |
| Systematic IUPAC name
3-Methylbutyl formate | |
| Other names
Isopentyl formate
Isopentyl methanoate Isoamyl formate | |
| Identifiers | |
3D model (JSmol)
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| 1739893 | |
| ChEBI | |
| ChEMBL | |
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PubChem CID
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| Properties | |
| C6H12O2 | |
| Molar mass | 116.160 g·mol−1 |
| Appearance | Colorless liquid |
| Odor | fruity (plum, blackcurrant) |
| Density | 0.881−0.889 g/cm3 |
| 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) |
| 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)
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1.396−1.400 |
| Hazards | |
| GHS pictograms |  
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| GHS Signal word | Danger |
| H225, H319, H335 | |
| P210, P233, P240, P241, P242, P243, P261, P264+265Script error: No such module "Preview warning".Category:GHS errors, P271, P280, P303+361+353, P304+340, P305+351+338, P319Script error: No such module "Preview warning".Category:GHS errors, P337+317Script error: No such module "Preview warning".Category:GHS errors, P370+378, P403+233, P403+235, P405, P501 | |
| Flash point | 27 °C[3] |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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| Related compounds | |
Related compounds
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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 C
6H
12O
2. 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
- ↑ 1.0 1.1 "Isopentyl formate". 10 February 2024. https://pubchem.ncbi.nlm.nih.gov/compound/Isopentyl-formate.
- ↑ "NT0185000". http://www.chemspider.com/Chemical-Structure.7761.html?rid=d7c27e48-ab57-432e-9223-08ae88de50dc.
- ↑ 3.0 3.1 3.2 3.3 Api, A.M.; Belsito, D.; Botelho, D.; Browne, D.; Bruze, M.; Burton Jr., G.A.; Buschmann, J.; Calow, P. et al. (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.
- ↑ "isoamyl formate". http://www.thegoodscentscompany.com/data/rw1019851.html.
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