酢酸イソアミル
WordNet
- a salt or ester of acetic acid (同)ethanoate
PrepTutorEJDIC
- 酢酸(さくさん)塩;アセテート(酢酸人造絹糸)
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/06/04 01:25:51」(JST)
[Wiki en表示]
Isoamyl acetate
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| Names |
| IUPAC name
3-Methylbut-1-yl acetate
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Other names
Isopentyl acetate
Banana oil
Isopentyl ethanoate
Pear essence
3-Methylbutyl acetate
3-Methylbutyl ethanoate |
| Identifiers |
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CAS Number
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123-92-2 Y |
| ChEBI |
CHEBI:31725 Y |
| ChEMBL |
ChEMBL42013 Y |
| ChemSpider |
29016 Y |
| Jmol 3D model |
Interactive image |
| KEGG |
C12296 Y |
| UNII |
Z135787824 Y |
InChI
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InChI=1S/C7H14O2/c1-6(2)4-5-9-7(3)8/h6H,4-5H2,1-3H3 Y
Key: MLFHJEHSLIIPHL-UHFFFAOYSA-N Y
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InChI=1/C7H14O2/c1-6(2)4-5-9-7(3)8/h6H,4-5H2,1-3H3
Key: MLFHJEHSLIIPHL-UHFFFAOYAI
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| Properties |
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Chemical formula
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C7H14O2 |
| Molar mass |
130.19 g·mol−1 |
| Appearance |
Colorless liquid |
| Odor |
Banana-like[1] |
| Density |
0.876 g/cm3 |
| Melting point |
−78 °C (−108 °F; 195 K) |
| Boiling point |
142 °C (288 °F; 415 K) |
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Solubility in water
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0.3% (20 °C)[1] |
| Vapor pressure |
4 mmHg (20 °C)[1] |
| Hazards |
| NFPA 704 |
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| Flash point |
25 °C (77 °F; 298 K) |
| Explosive limits |
1.0% (100 °C) - 7.5%[1] |
| Lethal dose or concentration (LD, LC): |
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LD50 (median dose)
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7422 mg/kg (rabbit, oral)
16,600 mg/kg (rat, oral)[2] |
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LCLo (lowest published)
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6470 ppm (cat)[2] |
| US health exposure limits (NIOSH): |
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PEL (Permissible)
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TWA 100 ppm (525 mg/m3)[1] |
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REL (Recommended)
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TWA 100 ppm (525 mg/m3)[1] |
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IDLH (Immediate danger)
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1000 ppm[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Y verify (what is YN ?) |
| Infobox references |
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Isoamyl acetate, also known as isopentyl acetate, is an organic compound that is the ester formed from isoamyl alcohol and acetic acid. It is a colorless liquid that is only slightly soluble in water, but very soluble in most organic solvents. Isoamyl acetate has a strong odor which is also described as similar to both banana and pear.[3] Banana oil is a term that is applied either to pure isoamyl acetate or to flavorings that are mixtures of isoamyl acetate, amyl acetate, and other flavors.[4]
Contents
- 1 Production
- 2 Applications
- 3 Occurrence in nature
- 4 References
Production
Isoamyl acetate is prepared by the acid catalyzed reaction (Fischer esterification) between isoamyl alcohol and glacial acetic acid as shown in the reaction equation below. Typically, sulfuric acid is used as the catalyst. Alternately, an acidic ion exchange resin can be used as the catalyst.
Applications
Isoamyl acetate is used to confer banana flavor in foods. Pear oil commonly refers to a solution of isoamyl acetate in ethanol that is used as an artificial flavor.
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. As a solvent and carrier for materials such as nitrocellulose, it was extensively used in the aircraft industry for stiffening and wind-proofing fabric flying surfaces, where it and its derivatives were generally known as 'aircraft dope'. Now that most aircraft are all-metal, such use is now mostly limited to historically accurate reproductions and scale models.
Because of its intense, pleasant odor and its low toxicity, isoamyl acetate is used to test the effectiveness of respirators or gas masks.
Occurrence in nature
Banana oil is made naturally by the banana plant;[5] it is also produced synthetically.[6]
Isoamyl acetate is released by a honey bee's sting apparatus where it serves as a pheromone beacon to attract other bees and provoke them to sting.[7]
References
- ^ a b c d e f g "NIOSH Pocket Guide to Chemical Hazards #0347". National Institute for Occupational Safety and Health (NIOSH).
- ^ a b "Isoamyl acetate". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).
- ^ "Iso-amyl acetate". chemicalland21.com.
- ^ Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe, Horst Surburg "Flavors and Fragrances" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a11_141.
- ^ McGee, Harold (2003). On Food and Cooking. New York: Scribner.
- ^ Isoamyl Acetate, Occupational Safety and Health Administration
- ^ 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 (4845): 1018–20. doi:10.1038/1951018b0. PMID 13870346.
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Esters
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| Methyl Esters |
- Methyl formate
- Methyl acetate
- Methyl propionate
- Methyl butyrate
- Methyl pentanoate
- Methyl hexanoate
- Methyl heptanoate
- Methyl octanoate
- Methyl nonanoate
- Methyl decanoate
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| Ethyl Esters |
- Ethyl formate
- Ethyl acetate
- Ethyl propionate
- Ethyl butyrate
- Ethyl pentanoate
- Ethyl hexanoate
- Ethyl heptanoate
- Ethyl octanoate
- Ethyl nonanoate
- Ethyl decanoate
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| Propyl Esters |
- Propyl formate
- Propyl acetate
- Propyl propanoate
- Isopropyl acetate
- Isopropyl palmitate
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| Butyl Esters |
- Butyl formate
- Butyl acetate
- Butyl propanoate
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| Amyl Esters |
- Amyl formate
- Amyl acetate
- Isoamyl acetate
- Sec-Amyl acetate
- Pentyl propanoate
- Pentyl butyrate
- Pentyl pentanoate
- Pentyl hexanoate
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UpToDate Contents
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English Journal
- Selection of aroma compounds for the differentiation of wines obtained by fermenting musts with starter cultures of commercial yeast strains.
- Vararu F1, Moreno-García J2, Zamfir CI3, Cotea VV1, Moreno J4.
- Food chemistry.Food Chem.2016 Apr 15;197(Pt A):373-81. doi: 10.1016/j.foodchem.2015.10.111. Epub 2015 Nov 11.
- Nine wines obtained by fermenting Aligoté musts with individual starter cultures of eight Saccharomyces cerevisiae yeast strains and with the indigenous microbiota were compared in terms of their composition in minor volatile aroma compounds. An easy handle methodology Stir-Bar-Sorptive-Adsorption,
- PMID 26616963
- Acidic electrolyzed water efficiently improves the flavour of persimmon (Diospyros kaki L. cv. Mopan) wine.
- Zhu W1, Zhu B1, Li Y1, Zhang Y2, Zhang B1, Fan J3.
- Food chemistry.Food Chem.2016 Apr 15;197(Pt A):141-9. doi: 10.1016/j.foodchem.2015.10.106. Epub 2015 Oct 23.
- The ability of acidic (AcW) and alkaline electrolyzed waters (AlW) to improve the flavour of persimmon (Diospyros kaki L.) wine was evaluated. Wines made with AcW (WAcW) were significantly better than wines made with AlW or pure water (PW) in aroma, taste, and colour. Volatile analysis showed that W
- PMID 26616934
- Transformation of chemical constituents of lychee wine by simultaneous alcoholic and malolactic fermentations.
- Chen D1, Liu SQ2.
- Food chemistry.Food Chem.2016 Apr 1;196:988-95. doi: 10.1016/j.foodchem.2015.10.047. Epub 2015 Oct 22.
- This work examined for the first time the impact of malolactic fermentation (MLF) on the chemical constituents of lychee wine. Oenococcus oeni Viniflora® Oenos (MLF inducer) and Saccharomyces cerevisiae MERIT.ferm were co-inoculated into lychee juice to induce simultaneous alcoholic fermentation (A
- PMID 26593581
Japanese Journal
- Classification of Chinese Rice Wine According to Geographic Origin and Wine Age Based on Chemometric Methods and SBSE-TD-GC-MS Analysis of Volatile Compounds
Related Links
- [Isoamyl Acetate] [123-92-2] | 価格や在庫、物性値などの詳細情報ページです。 ... 別名 (英名) Acetic Acid Isoamyl Ester 別名 (英名) Isopentyl Acetate 別名 (英名) 3-Methylbutyl Acetate 和名 酢酸イソアミル [吸光分析用]
- The undergraduate chemistry lab activity most clearly vivid in my memory is the day we made isoamyl acetate. It’s not an explosion or brightly coloured product or even an unusual glassware setup I remember. It’s the smell. After an hour of refluxing isoamyl alcohol and acetic acid – a combination ...
★リンクテーブル★
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- 英
- isoamyl acetate
- 同
- 酢酸イソペンチル isopentyl acetate