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Isoamyl formate

From Wikipedia, the free encyclopedia
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
3D model (JSmol)
1739893
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.428 Edit this at Wikidata
EC Number
  • 203-769-2
KEGG
UNII
  • InChI=1S/C6H12O2/c1-6(2)3-4-8-5-7/h5-6H,3-4H2,1-2H3
    Key: XKYICAQFSCFURC-UHFFFAOYSA-N
  • CC(C)CCOC=O
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)
1.396−1.400
Hazards
GHS labelling:
GHS02: Flammable GHS07: Exclamation mark
Danger
H225, H319, H335
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):
  • 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).

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

[edit]

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

[edit]

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

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

Safety

[edit]

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

References

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  1. ^ a b "Isopentyl formate". PubChem. 10 February 2024. Retrieved 13 February 2024.
  2. ^ "NT0185000". ChemSpider. Retrieved 13 February 2024.
  3. ^ a b c d 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.{{cite book}}: CS1 maint: multiple names: authors list (link)
  5. ^ "isoamyl formate". The Good Scents Company. Archived from the original on 22 July 2023.