Synthesis of Isoamyl Acetate for Air Freshener Application

Total Page：16

File Type：pdf, Size：1020Kb

SYNTHESIS OF ISOAMYL ACETATE FOR AIR FRESHENER APPLICATION Christian A. Malapit Organic Chemistry Laboratory Department of Chemistry Ateneo de Manila University Esters are a class of compounds widely distributed in nature. The simple esters tend to have pleasant odors. In many cases, although not exclusively so, the characteristic flavors and fragrances of flowers and fruits are due to compounds with the ester functional group. An exception is the case of the essential oils. The odors and flavors of fruits and flowers may often be due to a single ester, but more often, it is due to a complex mixture in which a single ester predominates. In this experiment, you will prepare an ester, isoamyl acetate (isopentyl acetate). This ester is ofter referred to as banana oil, since it has the familiar odor of this fruit. Isoamyl acetate is used to confer banana flavor in foods. It is also used as a solvent for some varnishes and nitrocellulose lacquers, as well as being a honey bee pheromone and can be used to attract large groups of honeybees to a small area. Isoamyl acetate is prepared by the direct acid-catalyzed esterification of acetic acid with isoamyl alcohol as seen in scheme 1. Scheme 1. Acid-catalyzed esterification of isoamyl alcohol and acetic acid to form isoamyl acetate. Procedure A. Synthesis of isoamyl acetate In 50 mL round bottom flask, mix 15 mL of isoamyl alcohol, 12 mL glacial acetic acid and 4.0 mL concetrated sulfuric acid. Swirl the solution and add boiling chips. Set-up reflux apparatus and heat the mixture for 20 to 30 minutes. Allow the mixture to cool to room temperature then transfer it in a separatory funnel. Wash the mixture with cold 25 mL of 5 % aqueous sodium bicarbonate solution. Do this 2 to 3 times. Collect the upper layer and dry it over anhydrous sodium sulfate. Perform hydroxamic acid test and determine the mass and density of the product. Report the % yield of the reaction. B. Formulation of an air freshener Prepare an unscented gelatin (carrageenan-based gelatin). The usual preparation is done by dissolving the solid gelatin sample in enough boiling water. Allow the mixture to cool. Before the solution turns gel, add the synthesized isoamyl acetate (15-20 parts gelatin to 1 part isoamyl acetate by volume). Continue mixing then place the gel in a molder or container. Package and label the product. References Figures can be accessed at: http://en.wikipedia.org/wiki/Isoamyl_acetate or by searching ‘banaba’ and ‘pear’. Boch R; Shearer DA, Stone BC (September 8, 1962). "Identification of isoamyl acetate as an active component in the sting pheromone of the honey bee.". Nature (England: Nature Publishing Group) 195: 1018–20. .

Copy Link

Recommended publications

Effect of Enzymes on Strawberry Volatiles During Storage, at Different Ripeness
Effect of Enzymes on Strawberry Volatiles During Storage, at Different Ripeness Level, in Different Cultivars and During Eating Thesis Presented in Partial Fulfillment of the Requirements for the Degree Master of Science in the Graduate School of The Ohio State University By Gulsah Ozcan Graduate Program in Food Science and Technology The Ohio State University 2010 Thesis Committee: Sheryl Ann Barringer, Adviser W. James Harper John Litchfield 1 Copyright by Gülşah Özcan 2010 ii ABSTRACT Strawberry samples with enzyme activity and without enzyme activity (stannous chloride added) were measured for real time formation of lipoxygenase (LOX) derived aroma compounds after 5 min pureeing using selected ion flow tube mass spectrometry (SIFT-MS). The concentration of (Z)-3-hexenal and (E)-2-hexenal increased immediately after blending and gradually decreased over time while hexanal concentration increased for at least 5 min in ground strawberries. The formation of hexanal was slower than the formation of (Z)-3-hexenal and (E)-2-hexenal in the headspace of pureed strawberries. The concentration of LOX aldehydes and esters significantly increased during refrigerated storage. Damaging strawberries increased the concentration of LOX aldehydes but did not significantly affect the concentration of esters. The concentrations of many of the esters were strongly correlated to their corresponded acids and/or aldehydes. The concentration of LOX generated aldehydes decreased during ripening, while fruity esters increased. Different varieties had different aroma profiles and esters were the greatest percentage of the volatiles. The aroma release of some of the LOX derived aldehydes in the mouthspace in whole strawberries compared to chopped strawberries showed that these volatiles are formed in the mouth during chewing.
[Show full text]
Fermentation and Ester Taints
Fermentation and Ester Taints Anita Oberholster Introduction: Aroma Compounds • Grape‐derived –provide varietal distinction • Yeast and fermentation‐derived – Esters – Higher alcohols – Carbonyls – Volatile acids – Volatile phenols – Sulfur compounds What is and Esters? • Volatile molecule • Characteristic fruity and floral aromas • Esters are formed when an alcohol and acid react with each other • Few esters formed in grapes • Esters in wine ‐ two origins: – Enzymatic esterification during fermentation – Chemical esterification during long‐term storage Ester Formation • Esters can by formed enzymatically by both the plant and microbes • Microbes – Yeast (Non‐Saccharomyces and Saccharomyces yeast) – Lactic acid bacteria – Acetic acid bacteria • But mainly produced by yeast (through lipid and acetyl‐CoA metabolism) Ester Formation Alcohol function Keto acid‐Coenzyme A Ester Ester Classes • Two main groups – Ethyl esters – Acetate esters • Ethyl esters = EtOH + acid • Acetate esters = acetate (derivative of acetic acid) + EtOH or complex alcohol from amino acid metabolism Ester Classes • Acetate esters – Ethyl acetate (solvent‐like aroma) – Isoamyl acetate (banana aroma) – Isobutyl acetate (fruit aroma) – Phenyl ethyl acetate (roses, honey) • Ethyl esters – Ethyl hexanoate (aniseed, apple‐like) – Ethyl octanoate (sour apple aroma) Acetate Ester Formation • 2 Main factors influence acetate ester formation – Concentration of two substrates acetyl‐CoA and fusel alcohol – Activity of enzyme responsible for formation and break down reactions • Enzyme activity influenced by fermentation variables – Yeast – Composition of fermentation medium – Fermentation conditions Acetate/Ethyl Ester Formation – Fermentation composition and conditions • Total sugar content and optimal N2 amount pos. influence • Amount of unsaturated fatty acids and O2 neg. influence • Ethyl ester formation – 1 Main factor • Conc. of precursors – Enzyme activity smaller role • Higher fermentation temp formation • C and N increase small effect Saerens et al.
[Show full text]
Isoamyl Acetate
SUMMARY OF DATA FOR CHEMICAL SELECTION Isoamyl Acetate CAS No. 123-92-2 Prepared for NTP by Technical Resources International, Inc Prepared on 11/94 Under NCI Contract No. N01-CP-56019 Table of Contents I. Chemical Identification II. Exposure Information Table 1. Levels of isoamyl acetate reported in foods III. Evidence for Possible Carcinogenic Activity Appendix A: Structural Analogs of Isoamyl Acetate IV. References SUMMARY OF DATA FOR CHEMICAL SELECTION CHEMICAL IDENTIFICATION CAS Registry No.: 123-92-2 Chem. Abstr. Name: 1-Butanol, 3-methyl-, acetate Synonyms: Acetic acid 3-methylbutyl ester; acetic acid, isopentyl ester; AI3-00576; banana oil; isoamyl ethanoate; isopentyl acetate; isopentyl alcohol, acetate; pear oil; 3-methyl-1-butanol acetate; 3-methyl-1-butyl acetate; 3-methylbutyl acetate; 3-methylbutyl ethanoate; i-amyl acetate Structure: Molecular Formula and Molecular Weight: C7H14O2 Mol. Wt.: 130.18 Chemical and Physical Properties: Description: Colorless, flammable liquid with a banana-like odor (ACGIH, 1993). Boiling Point: 142°C (Lide, 1993) Melting Point: -78.5°C (Mark, et al, 1984; Lide, 1993) Solubility: Soluble in water (2000 mg/L at 25°C) (Howard, 1990); soluble in ethanol, diethyl ether, and acetone (Lide, 1993). Vapor 4.5 mm Hg at 20°C (Howard, 1990) Pressure: Refractive 1.4003 (Lide, 1993) Index: Flash Point: closed cup, 33°C; open cup, 38°:C (Budavari, 1989) Density: 0.876 (Lewis, 1993) Reactivity: Thermal decomposition of isoamyl acetate may produce acrid fumes. Contact with strong oxidizing agents, strong acids, and alkaline materials should be avoided (Haarmann & Reimer Corp., 1994). Hazardous decomposition products of isoamyl acetate include CO and CO2 (AESAR/Alfa, 1994) Log 2.13 (Howard, 1990) P(octanol/water partition coefficient): Technical Isoamyl acetate is commercially available as both a natural and synthetic product with a purity Products and range of 95-99+%.
[Show full text]
United States Patent (19) 11 Patent Number: 4,917,822 Thiel Et Al
United States Patent (19) 11 Patent Number: 4,917,822 Thiel et al. (45) Date of Patent: Apr. 17, 1990 (54) GRAPHITE-CONTAINING CONDUCTIVE (56) References Cited SUSPENSION FOR PICTURETUBES U.S. PATENT DOCUMENTS 75) Inventors: Norbert Thiel, Bad Säckingen; Rolf 3,923,697 12/1975 Ellis ..................................... 252/506 Zondler, Straubing-Ittling, both of 4,038,091 7/1977 Francel et al. ........................ 501/15 Fed. Rep. of Germany 4,098,611 7/1978 Francel et al. ........................ 501/15 4,099,977 7/1978 Francel et al. ........................ 50/15 (73) Assignee: Nokia Graetz, Pforzheim, Fed. Rep. 4,547,310 10/1985 Kasanami et al. .................. 252/511 of Germany 4,613,375 9/1986 Förster et al. ...................... 252/511 (21) Appl. No.: 193,372 Primary Examiner-Josephine Barr Attorney, Agent, or Firm-Peter C. Van der Sluys (22 Filed: May 12, 1988 57 ABSTRACT Related U.S. Application Data A conductive suspension for making contact to the inside of a picture tube consists of graphite, glass-frit 63 Continuation-in-part of Ser. No. 108,066, Oct. 13, 1987, powder, a binder, such as nitrocellulose, a solvent, such abandoned. as isoamyl acetate. It can be applied prior to or after the (30) Foreign Application Priority Data aluminizing process by various techniques, such as brushing, printing, or spraying, and permits the bake Oct. 16, 1986 DE Fed. Rep. of Germany ....... 3636186 out process and the frit-sealing process to be performed 511 Int. Cl." ............................................... H01B 1/06 in one step because it is permeable to organic sub 52 U.S. C. .................................... 252/511; 252/502; stances.
[Show full text]
Characterization of Key Aroma Compounds in Xiaoqu Liquor and Their Contributions to the Sensory Flavor
beverages Article Characterization of Key Aroma Compounds in Xiaoqu Liquor and Their Contributions to the Sensory Flavor Zhe Wang 1,2, Xizhen Sun 2, Yuancai Liu 2 and Hong Yang 1,* 1 College of Food Science and Technology, Huazhong Agricultural University, Wuhan 430070, China; [email protected] 2 Hubei Provincial Key Lab for Quality and Safety of Traditional Chinese Medicine Health Food, Jing Brand Research Institute, Jing Brand Co., Ltd., Daye 435100, China; [email protected] (X.S.); [email protected] (Y.L.) * Correspondence: [email protected]; Tel.: +86-027-8728-2111 Received: 25 May 2020; Accepted: 27 June 2020; Published: 1 July 2020 Abstract: The objective of this study was to investigate the aroma profile and major flavor compounds in Xiaoqu liquor by a combination of sensory profiling, GC-O/GC-MS analysis, and SBSE-GC-MS. A total of 57 important volatile compounds (FD 2) were screened based on the retention ≥ indices, aromatic characteristics, standard comparison, and aroma extract dilution analysis (AEDA). By calculating the odor activity values (OAVs), 32 aroma active compounds were identified in Xiaoqu liquor. In the aroma recombination experiments, these active compounds were dissolved in 46% ethanol water at their natural concentrations, resulting in successful simulations of the typical aromas of Xiaoqu liquor, including fruity aroma, sweet aroma, and grain aroma. Omission experiments showed that the critical compounds that contribute to the characteristic flavor of Xiaoqu liquor include ethyl octanoate, acetaldehyde, 1,1-diethoxyethane, isoamyl acetate, ethyl acetate, valeric acid, 1-octen-3-ol, and ethyl isovalerate. The results provide some guidance for upgrading the fermentation and microbial strain in the production of Xiaoqu liquor.
[Show full text]
Isoamyl Acetate
isoamyl acetate CAS number: 123-92-2 IUPAC: 3-methylbut-1-yl ethanoate; SMILES (Simplified MoleCular Input Line-Entry System): O=C(OCCC(C)C)C Molecular Formula: C7H14O2 Mol. Wt.: 130.18 Colorless, flammable liquid with a banana-liKe odor (ACGIH, 1993). Isoamyl aCetate is CommerCially available as both a natural and synthetiC produCt with a purity range of 95-99+%. (Allured Publishing Corp., 1993; AldriCh ChemiCal Co., InC., 1994; Pfaltz & Bauer, 1994) Use Pattern: Isoamyl aCetate is used as a solvent for tannins, nitrocellulose, lacquers, Celluloid, and Camphor. It is also used as a flavoring agent in soft drinKs, Chewing gum, and Candies. Isoamyl aCetate is used during the manufaCturing proCess of artifiCial silK, leather, pearls, photographiC films, Celluloid Cements, waterproof varnish, bronzing liquids, metalliC paints, dyeing, and finishing teXtiles (Howard, 1990). Isoamyl aCetate is used in the following produCts at the following typiCal ConCentrations (%): soap, 0.05; detergent, 0.005; Creams, lotions, 0.003; perfume, 0.05 (OpdyKe, 1975). Isoamyl aCetate has reportedly been used in the following produCts at the following levels: non-alCoholiC beverages, 28 ppm; iCe Cream, iCes, etC, 56 ppm; Candy, 190 ppm; baKed goods, 120 ppm; gelatins and puddings, 100 ppm; and Chewing gum, 2700 ppm (Furia & Bellanca, 1975). Occurrence: Isoamyl aCetate is a plant volatile. It is released during the fermentation proCess in maKing beer and whisKey. It is a sting pheromone of the honey bee (Apis mellifera), and can be used to attraCt large groups of honeybees to a small area. The Compound is released by the honey bee when it stings and the resulting sCent Calls other bees to sting the viCtim.
[Show full text]
Annex I: Clinical Evidence Regarding Sensitisation to Individual Fragrance Chemicals and to Natural Extracts
Annex I: Clinical evidence regarding sensitisation to individual fragrance chemicals and to natural extracts Contents Single chemicals ............................................................................. 2 Catalogue of single chemicals evaluated ............................................. 5 Natural extracts / essential oils ........................................................68 Catalogue of natural extracts / essential oils evaluated ........................68 References ....................................................................................99 1 Single chemicals Often, results with the single constituents of the FM I or, yet more rarely, FM II, are presented in one paper. As the main ordering is by allergen, core information on these studies is presented in a tabular format and referenced by a unique acronym in the single sections, to avoid redundancy. Regarding nomenclature, terms which are often not officially an INCI Name but Perfuming Name as listed by CosIng are used. Table 1: Background information on studies reporting results with (all) single constituents of the FM I (amyl cinnamal, cinnamyl alcohol, cinnamal, eugenol, geraniol, hydroxycitronellal, isoeugenol, EVERNIA PRUNASTRI) Reference Country Study period, Comments by Patients reviewers Larsen 2002 c 7 industrial countries Prior to 2002 Test concentrations (1) worldwide n=218 patients with identified as non- known contact allergy irritating in serial to fragrance dilution testing in 20 ingredients healthy volunteers Utrecht 1999 Utrecht, The Netherlands
[Show full text]
Fermentation-Derived Aroma Compounds in Varietal Young Wines from South Africa
Fermentation-derived Aroma Compounds in Varietal Young Wines from South Africa L. Louw1 ' 2 , A.G.J. Tredoux1, P. Van Rensburg 1 ' 2 , M. Kidd3, T. Naes4 and H.H. Nieuwoudt 1 (1) Institute for Wine Biotechnology, Department of'Viticulture and Oenology, Stellenbosch University, Private Bag Xl, 7602, Matieland, South Africa (2)Distell Ltd., P.O. Box 184, Stellenbosch 7602, South Africa (3) Centre for Statistical Consultation, Stellenbosch University, Private Bag Xl, Matieland 7602, South Africa (4)Nofima Mat, Oslovegen 1, 1430 As, Norway Submitted for publication: May 2010 Accepted for publication: September 2010 Key words: South African young wines, GC-FID, aroma compounds, odour activity, discriminant analysis The volatile composition of 925 single cultivar young Sauvignon blanc, Chardonnay, Pinotage, Merlot, Shiraz and Cabernet Sauvignon wines of vintages 2005 to 2007, was determined using gas chromatography - flame ionisation detection. Compositional data were compared to published data on young wines from South Africa and other countries. South African young wines analysed in this study had a largely similar volatile composition to that reported in the literature. Significant between-vintage and between-cultivar differences were observed in the volatile composition of the wines investigated in this study. The concentration ranges of four compounds in red wines, hexanol, propanol, diethyl succinate and ethyl lactate, and four compounds in white wines, 2-phenylethanol, hexanoic acid, isoamyl acetate and propanol, were not influenced by vintage effects. This finding was interpreted as the first indication that typical concentration ranges for some aroma compounds can be established for South African young cultivar wines. A trend was observed in the white wines that the alcohols and their respective acetate esters, as well as fatty acids and their ethyl esters, were responsible for the vintage-related effects.
[Show full text]
Names & Synonyms Pdf Icon[PDF – 126
V.c. INDEX OF NAMES AND SYNONYMS Example: The references to method title and number are listed in the following manner: ACETIC ACID, 1603 (Method Title) Ethanoic acid, see ACETIC ACID, 1603 (Synonym) Glacial acetic acid, see ACETIC ACID, 1603 (Synonym) Methane carboxylic acid, see ACETIC ACID, 1603 (Synonym) CAS #64-19-7, see ACETIC ACID, 1603 (Chemical Abstracts Registry Number) Acenaphthene, see POLYNUCLEAR AROMATIC HYDROCARBONS, 5506 (HPLC); 5515 (GC) Acenaphthylene, see POLYNUCLEAR AROMATIC HYDROCARBONS, 5506 (HPLC); 5515 (GC) ACETALDEHYDE, 2538 (GC), 3507 (HPLC), see ALDEHYDES, SCREENING, 2539; ALIPHATIC ALDEHYDES, 2018 ACETIC ACID, 1603 Acetic acid anhydride, see ACETIC ANHYDRIDE, 3506 Acetic acid ethyl ester, see ETHYL ACETATE, 1457 Acetic acid butyl ester, see ESTERS I, 1450 Acetic acid 1,1-dimethylethyl ester, see ESTERS I, 1450 Acetic acid ethylene glycol monoethyl ether ester, see ESTERS I, 1450 Acetic acid isobutyl ester, see ESTERS I, 1450 Acetic acid 3-methyl-1-butanol ester, see ESTERS I, 1450 Acetic acid methyl ester, see METHYL ACETATE, 1458 Acetic acid 4-methyl-2-pentanol ester, see ESTERS I, 1450 Acetic acid 1-methyl propyl ester, see ESTERS I, 1450 Acetic acid 1-pentanol ester, see ESTERS I, 1450 Acetic acid 2-pentanol ester, see ESTERS I, 1450 Acetic acid n-propyl ester, see ESTERS I, 1450 Acetic acid vinyl ester, see VINYL ACETATE, 1453 Acetic aldehyde, see ACETALDEHYDE (GC), 2538; 3507 (HPLC) ACETIC ANHYDRIDE, 3506 Acetic ether, see VOLATILE ORGANIC COMPOUNDS (SCREENING), 2549 ACETOIN, 2558 Acetone, see KETONES I,
[Show full text]
Process Modelling of Isoamyl Acetate Synthesis Catalysed by Lipase from Candida Antarctica in a Solvent-Free System
Journal of Engineering Science, Vol. 10, 59–71, 2014 Process Modelling of Isoamyl Acetate Synthesis Catalysed by Lipase from Candida antarctica in a Solvent-free System Leong Sim Siong, Nurhazwani Yusoff Azudin and Syamsul Rizal Abd Shukor* School of Chemical Engineering, Universiti Sains Malaysia, Engineering Campus, 14300 Nibong Tebal, Pulau Pinang, Malaysia *Corresponding author: [email protected] Abstract: The objective of this work is to propose a reaction mechanism and develop a model for the synthesis of isoamyl acetate from isoamyl alcohol and acetate anhydride by using lipase from Candida antarctica in a solvent-free system. Ping-Pong Bi-Bi reaction mechanism with acetic anhydride and acetic acid inhibition is found to be the mechanism which is able to describe this reaction. Unknown parameters of the model developed are obtained by minimising deviation of model prediction from experimental result and it is performed by the Solver Tool in Microsoft Excel. The model prediction is found to match the experimental data quite well (average percentage error = 8.08%). Keywords: Isoamyl acetate, ester, process modelling, Ping-Pong Bi-Bi, solvent-free system 1. INTRODUCTION Ester is a class of chemical compounds which contains carbonyl group (–COO–) as the functional group. Many short-chain esters have distinctive fruit- like odours, and many esters exist naturally in the essential oils of plants.1 Generally, different esters are responsible for different specific fruity fragrances. However, very often one single compound plays a leading role. Due to its unique characteristic, esters are widely used in flavour, fragrance, food, cosmetic and pharmaceutical industries.2 Isoamyl acetate is an ester which is a clear, colourless liquid with a banana-like odour.
[Show full text]
Decrease of Wine Volatile Aroma Esters by Oxidation
View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Stellenbosch University: SUNJournals Decrease of Wine Volatile Aroma Esters by Oxidation M. Patrianakou and I.G. Roussis* Laboratory of Food Chemistry, Department of Chemistry, University of Ioannina, 45110 Greece Date of submission for publication: February 2013 Date of acceptance for publication: July 2013 Key words: Wine, ester, oxidation The effect of oxidation on the levels of wine volatile aroma esters was studied. Chardonnay wine was bottled either in the presence of nitrogen or air in the headspace. Moreover, Fe II was added to the wine and the bottles were closed in the presence of air. Absorbance values were recorded at 420 nm (browning index), while volatile esters were evaluated during storage using SPME/GC-MS. During wine storage of up to nine months, wines bottled in the presence of air exhibited higher browning indexes and lower levels of several esters, such ethyl acetate, isoamyl acetate, ethyl hexanoate, ethyl octanoate and ethyl decanoate, in comparison to wines bottled under nitrogen. Addition of Fe II led to higher browning indexes and lower levels of several esters during wine storage. In addition, Fe II was added along with H2O2 to Chardonnay wine and the bottles were closed in the presence of air. These additions led to wines with higher browning indexes and lower levels of several esters during wine storage up to 40 days. The present results demonstrate that wine volatile aroma esters can be decreased by oxidation under semi-oxidative and forced oxidative conditions. As a result, oxidation should be taken into account in the decrease of aroma esters during wine storage.
[Show full text]
Synthesis of Esters
CHEM& 131 Esters Lab Synthesis of Esters Introduction Esters are a class of compounds widely distributed in nature. They have the general formula (R and R’ represent generic carbon groups.) O || R-C-OR’ The simple esters tend to have pleasant odors. In many cases, although not exclusively so, the characteristic flavors and fragrances of flowers and fruits are due to compounds with the ester functional group. An exception is the case of essential oils. The organoleptic qualities (odors and flavors) of fruits and flowers may often be due to a single ester, but more often the flavor or aroma is due to a complex mixture in which a single ester predominates. Some common flavor principles are listed below. Ester Odor isoamyl acetate banana ethyl acetate fingernail polish remover methyl salicylate wintergreen ethyl butyrate strawberry benzyl butyrate cherry ethyl propionate rum benzyl acetate peach methyl butyrate apple octyl acetate orange n-propyl acetate pear ethyl phenylacetate honey Food and beverage manufacturers are thoroughly familiar with these esters and often use them as additives to spruce up the flavor or odor of a dessert or beverage. Many times odors do not have a natural basis, as is the case with the “juicy fruit” principle, isopentenyl acetate. An instant pudding that has the flavor of rum may never have seen its alcoholic namesake—this flavor can be duplicated by the proper admixture, along with other minor components, of ethyl formate and isobutyl propionate. The natural flavor and odor are not exactly duplicated, but most people can be fooled. Often only a trained person with a high degree of gustatory perception, a professional taster, can tell the difference.
[Show full text]