Isoamyl Octanoate

Amyl Octanoate FEMA No. 2079 Amyl Caprylate Isoamyl Caprylate Isoamyl Octanoate 214.35/C13H2602/ CH3(CH2)6COOC5Hn colorless liq/ fruity v—ale, most fixed oils ss—prop glycol ins—gly, water/ 260° 1 mL in 7 mL 80% ale remains clear to 10 mL... 

SYNS ISOAMYL OCTANOATE ISOPENTYL OCTANOATE OCTANOIC ACID, ISOPENTYL ESTER... 

Octanoic acid, 3-methylbutyl ester isoamyl octanoate ... 

Isoamyl caproate. See Isoamyl hexanoate Isoamyl caprylate. See Isoamyl octanoate Isoamyl chloride CAS 107-84-6... 

Isoamyl nonylate. See Isoamyl nonanoate Isoamyl octanoate... 

Isopentyi nitrite. See Isoamyl nitrite Isopentyi nonanoate. See Isoamyl nonanoate Isopentyi octanoate. See Isoamyl octanoate 3-lsopentyloxy-1,2-propanediol. See 1 -Isoamyl glycerol ether... 

Octanoic acid, 2-hydroxypropyl ester. See Propylene glycol caprylate Octanoic acid, isopentyl ester. See Isoamyl octanoate... 

Isoamyl octanoate Isoamyl phenylacetate Isoamyl propionate Isoamyl pyruvate ... 

Isoamyl isovalerate Isoamyl octanoate Isoamyl phenethyl ether Isoamyl phenylacetate Isoamyl propionate Isoamyl salicylate Isoamyl tiqiate Isoamyl valerate Isobornyl acetate Isobornyl formate Isobornyl isovalerate Isobornyl methyl ether Isobornyl propionate Isobutyl alcohol Isobutyl angelate... 

Amyl octanoate Decyl propionate Ethyl undecanoate Isoamyl octanoate Isobutyl pelargonate Methyl laurate Octyl isovalerate Octyl neopentanoate... 

Ethyl hexanoate and octanoate were the predominant FA esters found in Tinta Negra wines, whereas diethyl succinate and ethyl lactate were the most abundant diprotic acid ethyl esters. According to the authors, the most sensory important flavors seem to be attributed to 3-methylbutan-l-ol, 2-phenylethanol, isoamyl acetate, diethyl succinate, 2-phenylethylace-tate, phenylacetaldehyde, y-nonalactone, ethyl hexanoate, ethyl octanoate, hexanoic acid, and octanoic acid. 

Propa, Propanoic acid Buta, butanoic acid Penta, pentanoic acid Hexa, hexanoic acid Hepta, heptanoic acid Octa, octanoic acid Nona, nonanoic acid Deca, decanoic acid Pal, palmitic acid St, stearic acid Piva, trimethylacetic acid Vers, Versatic acid a-BrHexa, a-bromohexanoic acid x-BrSt, a-bromostearic acid Me2(OH)Hexa, 2,5-dimethyl-2-hydroxyhexanoic acid a,a -DAC, a,a -dialkylcarboxylic acid Naph, naphthenic acid cy-PA, cyclopentylacetic acid cy-Hexa, cyclohexanecarhoxylic acid C7-C mix, C7-C9 mixture CB, chlorobenzene cy-Hexn, cyclohexane 1,2-DCE, 1,2-dichloro-ethane (i-Pr)2CO, diisopropyl ketone i-amOAc, isoamyl acetate i-amOH, isoamyl alcohol MIBK, 4-methyl-2-pentanone NB, nitrobenzene n-Hexn, n-hexane PE, petroleum ether TCB, 1,2,4-trichlorobenzene. 

Aroma compounds selected were isoamyl alcohol (lOOpL/L), isoamyl acetate (lOOpL/L), ethyl hexanoate (lOOpL/L), ethyl octanoate (40pL/L), ethyl decanoate (lOpL/L), octanal (lOOpL/L), P-ionone (lOOpL/L), y-decalactone (lOOpL/L), supplied by Aldrich (Steinheim, Germany). They are all slightly soluble in water except for isoamyl alcohol which is soluble in water. The hydrophobic constants of volatile compounds are expressed by Log P where P is the partition coefficient of the compound in water/octanol system. 

The interactions between aroma compounds and macromolecules from yeast released during alcoholic fermentation (F) and autolysis (A) were studied by the headspace technique (11). The values of infinite dilution activity coefficients of volatile compounds were measured in a model wine with and without macromolecules at Ig/L (Table I). The volatility of ethyl decanoate stays constant in the presence of both extracts. For ethyl hexanoate and octanal, the F extract produces a significant (P< 0.01) decrease in the activity coefficient, by 12 and 8% respectively. Conversely F extract increases the volatility of isoamyl alcohol and ethyl octanoate by 6 and 19% respectively. The A extract increases the volatility of ethyl hexanoate by 6% and the volatility of ethyl octanoate by 15%. These results demonstrate the complex influence of macromolecules from yeast released during fermentation or autolysis on the volatility of aroma compounds. 

The hydrophobic nature of the volatile substance seemed an important factor. The volatile compound with the highest hydrophobic constant (log P = 3.88), ethyl octanoate, is bound to a larger extent on yeast walls. Conversely, isoamyl alcohol, with log P= 1.21, is less fixed the decrease in volatility is 9%. 

Iodine Potassium Iodide Dodecylbenzene Tridecyibenzene Hydroquinone Propionaldehyde Methylform amide Diacetone Alcohol Isoamyl Alcohol Pentanedione (2,4-) Acetylacetone Paraldehyde Butylaldehyde Butyraldehyde Levulinic Acid Dioctyl Adipate Acetic Acid Butyl Ester Butyl Acetate Dioxane (1,4-) Dioxane Dioxane (p-) Isoamyl Acetate Thiodiacetic Acid Butyl Stearate Santoprene 201-73 Kamax T-260 Adipic Acid Ethylene Chloroformate Caprylic Acid Octanoic Acid Hexamethylenediamine Butyl Carbitol Acetate Decane Carbon Dioxide Dimethylamine Sodium Methylate Freon 114B2 Tetrachloropentane Santicizer 141 Santoprene 201-64 Ecolan Hetron 99P Calcium Hydride Triton Sulfolane Tributyl Phosphate Tributylphosphate Sodium Diacetate Methacrylonitrile... 

The organic samples can also be injected directly into a GC without any preconcentration using a large volume on column system injection. This was tested in the case of liquid-liquid extraction with pentane/dichloromethane (2 1 v/v), by comparing the peak areas obtained with both injection methods for different compound categories present in wines in different levels, such as isoamyl acetate, acetoin, n-hexanol, trans 3-hexenol, cis 3-hexenol, ethyl octanoate, linalool, diethyl succinate, hexanoic and octanoic acids, N(3-methylbutyl)-acetamide, monoethyl succinate, 4-vinylphenol and 4-vinylguaiacol... 

As a consequence of the sensitivity of the method, higher values of the slope are reported for the hexanoate, octanoate and decanoate ethyl esters, and secondly for the isoamyl and 2-phenethyl acetates. On the contrary, 2-phenylethanol and ethyl acetate showed the smallest enrich-... 

Figure 5.4 GC-MS total ion current (TIC) chromatogram of a red Italian wine (Corvina) after HS- SPME automated aroma enrichment using a 1 cm CAR-PDMS-DVB fiber. 1. ethyl acetate, 2. ethanol, 3. isobutyl alcohol, 4. isoamyl acetate, 5. isoamyl alcohols, 6. ethyl hexanoate, 7. methyl heptanoate (I.S.), 8. linalyl ethylether, 9. 1-hexanol, 10. ethyl octanoate, 11. acetic acid, 12. geranyl ethylether, 13. linalool, 14. ethyl decanoate, 15. diethylsuccinate, 16. ethyl 9-decenoate, 17. 2-phenethyl acetate, 18. hexanoic acid, 19. 2-phenylethanol, 20. octanoic acid, 21. decanoic acid...

Among esters, compounds relevant in the characterization of the fruity aroma of wine are isoamyl acetate, hexyl acetate, 2-phenylethyl acetate and the ethyl esters of the hexanoic, octanoic and decanoic acids. Diethyl succinate is considered as an index of wine ageing and bacterial activity. For all these compounds and the corresponding fatty acids, there is a good linear correlation between XAD-2 enrichment and Kaltron liquid-liquid extraction. A little higher extraction, related to the internal standard, of Kaltron with respect to XAD-2 resin is obtained for most esters and acids, but not for the diethyl succinate and the... 

Figure 5.6 GC-MS analyses of a White Muscat wine by SPE wine aroma enrichment using a C18 pre-packed cartridge (a) and a XAD-2 hand-made cartridge (b) performed in the same analytical conditions (Versini et al., 1995). 1. isoamyl acetate, 2. ethyl hexanoate, 3. 1-hexanol, 4. linalool, 5. ho-trienol, 6. ethyl decanoate, 7. diethyl succinate, 8. a-terpineol, 9. trans pyran linalooloxide, 10. hexanoic acid, 11. Ho-diendiol (I), 12. octanoic acid, 13. Ho-diendiol (II), 14. diethyl 2-hydroxyglutarate, 15. hydroxycitronellol, 16. decanoic acid, 17. trans 8-hydroxylinalool, 18. cis 8-hydroxylinalool, 19. trans geranic acid, 20. 4-vinylphenol...

In addition to diacetyl, O. oeni produces esters, flavor compounds also important for wine flavor and aroma. Esters are primarily produced by Saccharomyces during alcoholic fermentation (Mason and Dufour, 2000 Nykanen, 1986 Nykanen and Nykanen, 1977 Soles et al., 1982), although evidence shows that esters such as ethyl acetate, ethyl lactate, ethyl hexano-ate, and ethyl octanoate can be synthesized by O. oeni (De Revel et al., 1999 Delaquis-Pascal et al., 2000 Edwards and Peterson, 1994 Maicas et al., 1999 Tracey and Britz, 1989). For example, Edwards and Peterson (1994) reported that strains of O. oeni synthesized relatively large amounts of ethyl lactate (183-1280 /ig/L) during growth in microbiological medium. In agreement, Maicas et al. (1999) reported that 50 mg/L of ethyl lactate was produced in wines fermented with O. oeni, as well as isoamyl acetate and ethyl caproate, compounds important for a pleasant fruity note in wine (Gil et al., 1996 Mason and Dufour, 2000 Nykanen, 1986). 

Figure 5.1. HS (headspace)-SPME-GC/MS chromatogram recorded in the analysis of a Gewiirztraminer wine volatiles performed using a CAR-PDMS-DVB fiber and the experimental conditions reported in Table 5.1. (1) ethyl hexanoate (2) 2- and 3-methyl-1-butanol (isoamyl alcohols) (3) ethyl lactate (4) 1-hexanol (5) ethyl octanoate (6) 1-heptanol (internal standard) (7) benzaldehyde (8) linalool (9) ethyl decanoate (10) diethyl succinate (11) a-terpineol (12) 2-phenylethyl acetate (13) 2-phenylethanol (14) octanoic acid.

Amyl nitrite. See Isoamyl nitrite Amyl octanoate... 

Synonyms Isoamyl caprylate Isopentyl octanoate 3-Methylbutyl octanoate Octanoic acid, isopentyl ester Octanoic acid, 3-methylbutyl ester... 

Ethyl octanoate Isoamyl isovalerate essence, fruit artificial Ethyl isovalerate Heptyl acetate Heptyl formate Isoamyl formate essential oils... 

Amyl phenylacetate Amyl valerate Amyris (Amyris balsamifera) oil trans-Anethole Anisaldehyde diethyl acetal Anise (Pimpinella anisum) extract p-Anisonitrile Anisyl alcohol o-Anisyl alcohol p-Anisyl isobutyrate Bay (Pimenta acris) oil Benzaldehyde propylene glycol acetal Benzothiazole Benzylacetone 2-Benzylheptanol Benzyl isoamyl ether Benzyl isovalerate Benzyl methyl ether Benzyl octanoate ... 

Dimethyloctanol PSiF 3,7-Dimethyl-1-octanol 106-22-9 Citronellol 80 Citronellol 96 FCC Citronellol AJ FCC 3-Citronellol 106-23-0 Citronellal Citronellal 80 106-24-1 Geraniol 106-25-2 Nerol Nerol 70 Nerolex FCC 106-26-3 Neral 106-27-4 Isoamyl butyrate 106-29-6 Geranyl butyrate 106-30-9 Ethyl heptanoate 106-31-0 Butyric anhydride 106-32-1 Ethyl octanoate... 

Isoamyl butyrate 203-381-3 Geranyl butyrate 203-382-9 Ethyl heptanoate 203-383-4 Butyric anhydride 203-385-5 Ethyl octanoate 203-386-0 Ethyl laurate 203-388-1 3-Heptanone 203-389-7 Propyl propionate Dear n-Propyl Propionate 203-390-2 1,4-Dibromobenzene 203-396-5 p-Xylene... 

Cyclohexanone diethyl acetal 2-Ethyl hexyl acetate Ethyl hydroxyheptyl ketone Ethyl octanoate Hexyl butyrate Hexyl Isobutyrate Hydroxycitronellal Isoamyl Isovalerate lsoamyl-2-methylbutyrate Isoamyl valerate Isobutyl hexanoate Isodecanolc acid p-Menthane-8-hydroperoxlde... 

Undecenol n-Undecenyl alcohol C11H22O2 Amyl hexanoate Butyl heptanoate 2-Ethylhexyl glycidyl ether Ethyl pelargonate Heptyl butyrate Heptyl isobutyrate Hexyl isovalerate Hexyl 2-methyl butyrate Hexyl neopentanoate Hexyl valerate Isoamyl hexanoate Isobutyl heptanoate Isohexyl neopentanoate Isononyl acetate Isopropyl octanoate Methoxycitronellal Methyl caprate n-Nonyl acetate Octyl propionate Propyl octanoate 3,5,5-Trimethylhexyl acetate Undecanoic acid... 

Formaldehyde ethyl cyclododecyl acetal Heptyl octanoate Isoamyl caprate Isodecyl neopentanoate Isopropyl laurate Lauryl glycidyl ether Methyl myristate Octyl heptanoate C15H30O3... 

Methylenebis (dimethylcyclohexylamine) C17H34O2 Isoamyl laurate Isopropyl myristate Methyl palmitate Myristyl propionate Nonyl octanoate Octyl isononanoate C17H34O3 Myristyl lactate Propylene glycol myristate C17H34O4... 

Esters constituted the largest family and included acetates (ethyl, propyl, isobutyl, butyl, isoamyl, and phenethyl), ethyl esters of fatty acids (propanoate, isobutanoate, butanoate, hexanoate, octanoate, 3-hydroxybutanoate, 3-hydroxyhexanoate and furcate), ethyl esters of organic acids (pyruvate, lactate, ethyl myristate, diethyl malate and, mono- and diethyl succinate) and various other esters, such as methyl butanoate, isobutyl lactate and phenylethyl octanoate. The acids quantified included isobutanoic, butanoic, hexanoic, octanoic, decanoic, lauiic and 3-methylbutanoic. The lactones included y-butyrolactone, pantolactone, y-decalactone and E- and Z-oak lactone and the terpenes included neral d-terpineol, P-dtronellol and Z-nerolidol. The aldehyde family comprised acetaldehyde, benzaldehyde, furfural, 5-methylfurfural and octanal, and the phenol family included eugenol, 4-ethylphenol and 4-ethylguaiacol. Finally, 1,1-diethoxyethane, acetoin, sotolon, 2, 3-butanedione, p-cymene and methionol were also determined. 

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