Chemical compound with plum odor
Isoamyl formate[ 1] [ 2]
Names
Preferred IUPAC name
Systematic IUPAC name
Other names
Isopentyl formate
Identifiers
1739893
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.428
EC Number
KEGG
UNII
InChI=1S/C6H12O2/c1-6(2)3-4-8-5-7/h5-6H,3-4H2,1-2H3
Key: XKYICAQFSCFURC-UHFFFAOYSA-N
Properties
C 6 H 12 O 2
Molar mass
−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;
Vapor pressure
9.97 mmHg (20 °C)
1.396−1.400
Hazards
GHS labelling
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).
Chemical compound
Isoamyl formate , also known as isopentyl formate , is an ester formed from isoamyl alcohol and formic acid , with the formula C6 H12 O2 . 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] 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
^ a b "Isopentyl formate" . PubChem . Retrieved 13 February 2024 .^ "NT0185000" . ChemSpider . Retrieved 13 February 2024 .^ 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 . ^ 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.
Methyl esters Ethyl esters Propyl esters Butyl esters Amyl esters Hexyl esters Phenyl esters Heptyl esters Benzyl esters
