Isoamyl Hexanoate, 512,

Isoamyl Hexanoate FEMA No. 2075 Amyl Hexanoate Isoamyl Caproate Pentyl Hexanoate 186.29/C H2202/ CH3(CH2)4COOCH2CH2CH(CH3)2 colorless liq/ fruity s—ale, most fixed oils ins—gly, prop glycol, water/ 222° 1 mL in 3 mL 80% ale gives clear soln... 

SYNS AMYL HEXANOATE FEMA No. 2075 ISOAMYL CAPROATE ISOAMYL HEXANOATE ISOPENTYL HEX.YNOATE ISOPENTYL-n-HEXANOATE... 

Geranyl phenylacetate 228 Isoamyl hexanoate 276 Methyl benzoate... 

Penta Mfg. http //www.pentamfg.com See aiso Isoamyl hexanoate... 

Amyl hexanoate. See Isoamyl hexanoate Amyl hexylate. See Amyl hexanoate Amyl hydride. See n-Pentane... 

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

CAS 109-25-1 EINECS/ELINCS 203-658-9 Synonyms 3-Methylbutyl heptanoate Toxicology TSCA listed Uses Fragrance in cosmetics flavor Manuf./Distrib. Advanced Synthesis Tech. http //WWW.advancedsynthesis.com, Grau Arom ati cs http //www.grau-aromatics. de Isoamyl hexanoate... 

Isoamyl cinnamate Isoamyl formate Isoamyl 4-(2-furan) butyrate Isoamyl 3-(2-furan) propionate Isoamyl hexanoate Isoamyl isobutyrate Isoamyl isovalerate Isoamyl laurate lsoamyl-2-methylbutyrate Isoamyl nonanoate... 

Isoamyl crotonate Isoamyl formate Isoamyl heptanoate Isoamyl hexanoate Isoamyl isobutyrate... 

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... 

Fntity Benzyl propionate Butyl acetate Cinnamyl anthranilate. formate Citronellyl acelate. butyrate, isobutyrate. propionate, Delta-decalactone Diethyl malunate Dimethylbenzyl carbinyl acetate Delta-dodecalactone Ethyl p-anlsate. benzoate, butyrate, heptanoate, hexanoate. maltol. nonanoate Isoamyl butyrate, hexanoate. isovalerate, cinnamate Linalyl isobutyrate. propionate Mallol Methyl benzoate, cinnamate 2-Methyl-undecanal, Nerohdol Octanol. Octyl formaie Phencthyl isobuiyrate. isovalerate gamma- Indecalactone. 

Figure 11.3 Partial fluxes of isoamyl alcohol, ethyl acetate, isoamyl acetate and ethyl hexanoate as a function of their feed crossflow velocity (bottom axis) and Reynolds number (top axis) in a singlechannel module, using a POMS-PEI composite membrane. Notice that external mass-transfer limitations are not fully overcome when soluteswith a high affinity towardsthe membrane are processed (Adapted from Ref. 32.)...

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. 

Polysaccharides, including starches and dextrins, have been shown to reduce the volatility of aroma compounds, such as limonene, isoamyl acetate, ethyl hexanoate and beta-ionones.237... 

Hexyl butanoate Butyl hexanoate Fenchyl acetate Menthyl acetate a-Terpinyl acetate Bornyl acetate Isobornyl acetate Linalyl acetate Citronellyl isobutyrate Phenethyl formate Anisyl formate Ethyl salicylate Pentyl salicylate isoamyl Salicylate hexyl Salicylate... 

Dimethoxy Phenol 3,4-Dimethyl 1,2-Cyclopen tandione 5-Ethyl 3-Hydroxy 4-Methyl 2(5H)-Furanone 3-Ethyl Pyridine Furfuryl Mercaptan Geranyl Isovalerate 2,3 -Heptandione (Z)-3-Hexenyl Butyrate (Z)-3-Hexenyl Formate Hexyl Butyrate Hexyl Hexanoate Isoamyl Isobutyrate Isobutyl Formate Isobutyl Hexanoate Linalool Oxide... 

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. 

Fig. 8F.1 Ethyl hexanoate (a) and isoamyl alcohol (b) partition coefficients [K (mol/mol)/(mol/mol)] at 25 °C in water, in 10 vol.% ethanol, and in 20 vol.% ethanol, with three static headspace methods PRV, VPC, and LC-SH (reprinted with permission from Athes et al. (2004) J Agile Food Chem 52 2021-2027. Copyright (2004) American Chemical Society)...

Interactions between mannoproteins from yeast cell walls and aroma compounds have been studied by Langourieux and Crouzet (1997). They performed the experiments with crude mannoproteins extracts and observed no effect on the activity coefficient of isoamyl acetate, and a slight decrease on the activity coefficients of ethyl hexanoate and limonene. However, when they purified the mannoproteins or when they used a model glycopeptide, they did not observe any effect on limonene volatility. If the synthetic peptide was heat treated (50 °C), they observed a slight reduction on the activity coefficient of limonene. This was explained by an increase in the hydrophobicity of the glycopeptide after the thermal treatment. 

Chalier et al. (2007), using mannoprotein at levels usually found in wines (150 mg/L), compared the effect of a whole mannoprotein extract (isolated from a synthetic medium subjected to alcoholic fermentation) to that of well characterized different mannoproteins fractions. From the four wine aroma compounds studied (isoamyl acetate, hexanol, ethyl hexanoate and /3-ionone), all except isoamyl acetate showed a decrease in volatility (up to 80%) when mannoproteins were present (Fig. 8F.3). They suggested that both the glycosidic and the peptidic parts of these macromolecules may be responsible for the interaction. They also found that the interactions of the whole mannoprotein extract Vs. mannoprotein fractions were different, suggesting that the conformational and compositional structure of these... 

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. 

Fining Agents. The binding capacity of caseinate, used for fining white and red wines was measured by heaspace analysis (Table III). Sodium caseinate at 1 g/L in model wine decreases the volatility of p-ionone more than that of ethyl hexanoate and isoamyl acetate. Like yeast walls, the most hydrophobic compound is the most bound to a larger extent. 

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). 

Phenylethyl Alcohol Ethyl Acetate Isoamyl Acetate Organic Acids Ethyl Hexanoate Methionol... 

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.

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