Isoamyl Acetate

HCID 31276CAS 123-92-2

基本情報

標準SMILES
CC(=O)OCCC(C)C
InChIKey
MLFHJEHSLIIPHL-UHFFFAOYSA-N
分子式
C7H14O2
平均分子量
130.18 g/mol
単同位体質量
130.09937969

概要

Iso-amyl acetate is an oily liquid; colorless; banana odor. Floats and mixes with water. Flammable, irritating vapor is produced. (USCG, 1999)

名称と識別子

優先名称
Isoamyl Acetate
IUPAC
3-methylbutyl acetate
現地名
酢酸イソアミル
英語名
Isoamyl acetate
分子式
C7H14O2
分子量
130.18

名称と別名

ISOAMYL ACETATE3-Methylbutyl acetate123-92-2Isopentyl acetateIsopentyl ethanoateIsoamyl ethanoate3-Methylbutyl ethanoateIsopentyl alcohol, acetate3-Methyl-1-butyl acetateAmylacetic ester3-Methyl-1-butanol acetateI-Amyl acetate
名称をさらに表示
酢酸イソアミルコモンアミルアセタートバナナオイル酢酸3-メチルブチルペアオイル3-メチルブチル=アセタート3-メチル-1-ブタノールアセタート酢酸イソペンチル西洋ナシ油イソアミル=アセタート酢酸ISO-ペンチルイソアミル酢酸酢酸イソペンチル(酢酸3-メチルブチル )酢酸アミルアミルアセテート酢酸イソアミル [吸光分析用]酢酸3‐メチルブチル酢酸3‐メチルブチル(異性体含有)酢酸 3 - メチルブチル酢酸イソペンチル( 酢酸 3 - メチルブチル )PENTYL ACETATE1-Butanol,3-methyl-,acetateFEMA 2055Banana oil
Iso-amyl acetate1-Butanol, 3-methyl-, acetateAcetic acid, isopentyl esterAmyl acetate, commonAcetic acid 3-methylbutyl ester3-Methyl-1-butanol, acetatebeta-Methylbutyl acetateFEMA No. 2055

データベース識別子

CAS
123-92-2
PubChem CID
31276
DTXSID
DTXSID9025453
ChEMBL
CHEMBL42013
ChEBI
CHEBI:31725
UNII
Z135787824
EC Number
204-662-3
Nikkaji
J2.012E

物性

構造計算による物性

XLogP
2
極性表面積
26.3 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
4
重原子数
9

実験および物理化学的性質

Chemical ClassesFlammable agents - 3rd degree
SolventsSolvents -> Esters (<C12)
Cosmetics · 2 件

Cosmetic ingredients (Isoamyl Acetate) -> CIR (Cosmetic Ingredient Review)

Solvent

SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Isoamyl acetate) -> IFRA transparency List
LogP · 4 件

log Kow = 2.25

2.25

2.13

2.55

物理化学的性質

融点
-78 °C · -78 °C (lit.)
沸点
142 °C/756 · 142 °C/756 mmHg (lit.)
比重(密度)
0.876 g/mL · 0.876 g/mL at 25 °C (lit.)
蒸気密度
4.5 · 4.5 (vs air)
蒸気圧
5 mm · 5 mm Hg ( 25 °C)
屈折率
20 · n20/D 1.4(lit.)
化学的性質 · 3 件

化学的特性イソアミル酢酸エステルは化学式C7H14O2で知られる化合物ですこれは香りの成分として知られており特にバナナのような甘くフルーティーな香りを持つため食品添加物や香料に広く使用されていますこのエステルは通常酢酸とイソアミルアルコールの化学反応によって製造されます

化学的特性Isoamyl Acetate is a strongly fruity-smelling liquid and has been identified in many fruit aromas. It is the main component of banana aroma and is, therefore, also used in banana flavors. All isomers of amyl acetate are highly flammable, colorless to yellow, watery liquids. Isoamyl acetate has a fruity, banana, sweet, fragrant, powerful odor with a bittersweet taste reminiscent of pear. If impure, the odor is strong, penetrating and almost shocking. In commercial practice, amyl invariably means isoamyl.

化学性质イソアミル酢酸エステルの合成はエステル化反応により行われますこのプロセスはイソアミルアルコールと酢酸を酸触媒の存在下で反応させることによってエステルイソアミル酢酸エステルと水が生成されます反応は以下の化学方程式で表されます

安全と法規制

GHS分類

GHS Classification · 6 件

Warning

H226: Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 2937) of reports.

Warning

H226 (> 99.9%): Flammable liquid and vapor [Warning Flammable liquids]

危険有害性情報

Regulatory Information · 6 件

Chemical: 1-Butanol, 3-methyl-, acetate

Regulation (EC) No 1831/2003 (amended)

1-Butanol, 3-methyl-, 1-acetate is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Butanol, 3-methyl-, 1-acetate are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 04-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13689

1-Butanol, 3-methyl-, acetate: HSNO Approval: HSR001171 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - 1-Butanol, 3-methyl-, acetate: Human health tier I assessment
DOT LabelFlammable Liquid
Fire Hazards · 2 件

FLAMMABLE. Flashback along vapor trail may occur. Vapor may explode if ignited in an enclosed area. When heated emits acrid fumes. When exposed to flames can react vigorously with reducing materials. (USCG, 1999)

Flammable. Above 25 °C explosive vapour/air mixtures may be formed.

Fire Potential · 3 件

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Highly flammable liquid when exposed to heat or flame; can react vigorously with reducing materials. Moderately explosive in the form of vapor when exposed to heat or flame.

Flammable liquid

Health HazardsVAPOR: Irritating to eyes, nose and throat. If inhaled, will cause nausea, headache or dizziness. LIQUID: Irritating to skin and eyes. Harmful if swallowed. (USCG, 1999)

安全と保護具

Fire Fighting · 2 件

Extinguish with dry chemical, alcohol foam, or carbon dioxide. Water may be ineffective on fire. Cool exposed containers with water. (USCG, 1999)

Use alcohol-resistant foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 件

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .

First Aid · 2 件

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

(General first aid procedures)

Safe StorageFireproof. Separated from strong oxidants.
Exposure Control and Personal Protection50.0 [ppm]
Fire Fighting Procedures · 5 件

...use alcohol foam, carbon dioxide, dry chemical.

/When fighting fire wear/ self-contained breathing apparatus with a full facepiece operated in pressure- demand or other positive pressure mode.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, carbon dioxide, or dry chemical. /Amyl acetate/

Use water spray to cool unopened containers.

For more Fire Fighting Procedures (Complete) data for ISOAMYL ACETATE (6 total), please visit the HSDB record page.

毒性情報

Target OrgansEyes, skin, respiratory system, central nervous system
Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 130(SRC), determined from a log Kow of 2.25(2) and a regression-derived equation(3), indicates that isoamyl acetate is expected to have high mobility in soil(SRC). Volatilization of isoamyl acetate from moist soil surfaces may be an important fate process(SRC) given a Henry's Law constant of 5.87x10-4 atm-cu m/mole(4). Isoamyl acetate is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.6 mm Hg at 25 °C(5). Biodegradation data in soil were not available(SRC, 2015). Structurally similar butyl acetate present at 100 mg/L, reached 86% of its theoretical BOD in 2 weeks using an activated sludge inoculum in the Japanese MITI test(6) suggesting that biodegradation of isoamyl acetate may be an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 130(SRC), determined from a log Kow of 2.25(2) and a regression-derived equation(3), indicates that isoamyl acetate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon a Henry's Law constant of 5.87 atm-cu m/mole(5). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 2 hours and 5 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 14(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2015). Structurally similar butyl acetate present at 100 mg/L, reached 86% of its theoretical BOD in 2 weeks using an activated sludge inoculum in the Japanese MITI test(7)suggesting that biodegradation of isoamyl acetate may be an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), isoamyl acetate, which has a vapor pressure of 5.6 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase isoamyl acetate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 5 days(SRC), calculated from its rate constant of 6.0x10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Isoamyl acetate does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values · 2 件

Isoamyl acetate was identified, not quantified, in nectarines(1), bananas(2), kiwi fruit(3), pork volatiles(4,5) and cheese products from the French Alps(6). Isoamyl acetate has been identified, not quantified, in whiskey(7), beer(8,11) and cognac(9,11). US lager beers have reported ester concentrations, such as isoamyl acetate, ranging from 25-50 ppm(10). Isoamyl acetate has been reported in apple, apricot, banana, currants, guava, grape, berries, melon, papaya, peach, pear, pineapple, sauerkraut, tomato, ginger, vinegar, wheat and rye bread, cured pork, grape wines, rum, whiskies, cider, sherry, cocoa, tea, soybeans, olive, passion fruit, plum, plumcot, beans, mushroom, starfruit, mango, quince, litchi, shoyu (fermented soy hydrolysate), sake, malt, elderberry juice, cherimoya, mountain papaya, nectarine, naranjilla fruit and Roman chamomile oil(11).

Isoamyl acetate was identified in the skin and pulp of Queen Anne's Pocket Melon (Cucumis melo var. dudaim (L.) Naudin) at concentrations of 280.7 and 334.9 ug/kg, respectively(1). Isoamyl acetate was identified in 2 of 3 commercial fermented soybean (Glycine max) curds prepared in Taiwan and Hong Kong at concentrations of 541.0 and 9027.4 ug/kg, respectively(2).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure Routes · 2 件

The substance can be absorbed into the body by inhalation of its vapour and by ingestion.

inhalation, ingestion, skin and/or eye contact

Milk ConcentrationsENVIRONMENTAL: Isoamyl acetate has been reported in cheeses, butter, and milk(1).

法規制情報

FDA Requirements · 1 件

Isoamyl acetate is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and b) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

TSCA Requirements · 2 件

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 1/26/94; Reporting date: 3/28/94.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Isoamyl acetate is included on this list. Effective date: 1/26/94; Sunset date: 6/30/98.

Atmospheric Standards · 1 件

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Isoamyl acetate is produced, as an intermediate or a final product, by process units covered under this subpart.

CERCLA Reportable Quantities · 1 件

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 5000 lb or 2270 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV.D.3.b).

Clean Water Act Requirements · 1 件

Isoamyl acetate is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance.

安全データ

OEB
A
OEL
TWA: 100 ppm (525 mg/m3)
wgk
1
IDLA
1,000 ppm
tsca
TSCA listed
rtecs
NS9800000

化学と産業

薬理情報

Biological Half-LifeNo reports found; [TDR, p. 95]
Cellular LocationsCytoplasm

用途と製造

Uses · 6 件

CIR ingredient: Isoamyl Acetate

Used as an additive to aerosols and cosmetics and to fit-test respirators; [ACGIH]

In alcohol solutions as a pear flavor in mineral waters and syrups; as solvent for old oil colors, for tannins, nitrocellulose, lacquers, celluloid and camphor; swelling bath sponges; covering unpleasant odors, perfuming shoe polish; manufacturing artificial silk, leather, or pearls, photographic films, celluloid cements, waterproof varnishes, bronzing liquids, and metallic paints; dying and finishing textiles. A special grade of the amyl acetate has been used for burning in the Hefner lamp serving as a photometric standard.

Industrial uses of amyl acetate include the following: ... as a warning odor; in the manufacture of ... artificial glass, and straw hats.

Flavoring, perfumes, solvent for nitrocellulose, masking undesirable odors.

In the manufacture of acetic acid by direct oxidation of a petroleum-based feedstock, solvent extraction has been used to separate acetic acid from the aqueous reaction liquor containing significant quantities of formic and propionic acids. Isoamyl acetate is used as solvent to extract nearly all the acetic acid, and some water, from the aqueous feed. The extract is then dehydrated by azeotropic distillation using isoamyl acetate as water entrainer.

U.S. Exports · 2 件

(1972) NEGLIGIBLE

(1975) NEGLIGIBLE

U.S. Production · 6 件

2023: 8,500,000 - <10,000,000 lb

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1984) 5.08X10+7 GRAMS

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 1-Butanol, 3-methyl-, 1-acetate. Aggregated National Production Volume: < 500,000 pounds.

Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 1-Butanol, 3-methyl-, 1-acetate. National Production Volume: 100,000 - 500,000 lb/yr.

Consumption PatternsABOUT 4.54X10+6 GRAMS PER YEAR IN FRAGRANCES (1974)
Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesFlavoring and nutrient
応用分野 · 7 件

解説酢酸イソアミル (英: Isoamyl acetate) とは、カルボン酸エステルに分類され、化学式C7H14O2で表される有機化合物の1種です。 IUPAC命名法による名称は酢酸3-メチルブチルであり、その他の別名に酢酸イソペンチルという名称があります。CAS登録番号は123-92-2です。カルボン酸エステル特有の果実臭を特徴として、特にバナナエッセンスなどの香料に用いられています。

用途香味料、香料、溶剤

説明In commercial practice amyl invariably means isoamyl, unless it is prefaced by the n- for normal. Isoamyl acetate has a powerful, fruity odor with a bittersweet taste reminiscent of pear. If impure, the odor is strong, penetrating, and almost shocking. Usually prepared by esterification of commercial isoamyl alcohol with acetic acid.

天然物の起源Reported to be found in a number of naturally occurring products, including apple, banana, cocoa bean, coffee, cognac, grape, peach, pear, pineapple and strawberry

使用Isoamyl acetate is used to impart pear flavorto mineral waters and syrups, in perfumes, inthe manufacture of artificial silk or leather, inphotographic films, in dyeing textiles, and asa solvent.

一般的な説明Oily liquid; colorless; banana odor. Floats and mixes with water. Flammable, irritating vapor is produced .

使用用途酢酸イソアミルの主な使用用途は、 香味料、香料、有機溶媒、溶剤です。 1. 香料 酢酸イソアミルは、バナナの香りの主成分であり、非常にフルーティーな香りの液体です。香料としては、バナナのフレーバー他、食品用の香料として使用されています。 また、日本酒の吟醸香の香気成分の1つでもあり、吟醸酒系の酒類が放つフルーティーな香りは酢酸イソアミル由来の香りです。 2. 溶剤・抽出剤 香料以外の用途では、酢酸イソアミルは、ニトロセルロース、エチルセルロース、樹脂の溶剤としてや塗料溶剤、印刷溶剤、シンナー、鉄・等の抽出剤などにも使用されています。

調製方法 · 3 件

製造方法By the esterification of commercial isoamyl alcohol with acetic acid

The commerical-grade isoamyl acetate is prepared by the esterification of amyl alcohol (often fusel oil) with acetic acid and a small amount of sulfuric acid as the catalyst .

純化方法Dry the acetate with finely divided K2CO3 and fractionally distil it. [Beilstein 2 IV 157.]

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補足説明

定義本品は、酢酸(*)とイソアミルアルコールのエステルであり、次の化学式で表される。参照表示名称:酢酸

定義ChEBI: The acetate ester of isoamylol.

関連反応

9 件

関連ノート

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