Isoamyl butyrate

HCID 7795CAS 106-27-4

Basic information

Standard SMILES
CCCC(=O)OCCC(C)C
InChIKey
PQLMXFQTAMDXIZ-UHFFFAOYSA-N
Molecular formula
C9H18O2
Average molar mass
158.24 g/mol
Monoisotopic mass
158.13067982

Overview

Isoamyl butyrate is the butanoate ester of isoamylol. It has a role as a metabolite. It is functionally related to an isoamylol.

Names & identifiers

Preferred name
Isoamyl butyrate
IUPAC
3-methylbutyl butanoate
English name
Isoamyl butyrate
Molecular formula
C9H18O2
Molecular weight
158.24

Names & synonyms

Isoamyl butyrateIsopentyl butyrate106-27-43-Methylbutyl butanoateButanoic acid, 3-methylbutyl esterISOPENTYL BUTANOATEIsoamyl butanoate3-Methylbutyl butyrateIsoamyl-n-butyrateButyric acid, isopentyl esterIsopentyl alcohol, butyrateFEMA No. 2060
Show more names
2-METHYLBUTYL BUTANOATEFEMA 20603-methyl-1-butylbutanoate3-methylbutyl
3-Methyl-1-butyl butanoateDTXSID3042059505AFM77VUNSC-6548DTXCID1022059CHEBI:87422RefChem:148996203-380-8

Database identifiers

CAS
106-27-4
PubChem CID
7795
DTXSID
DTXSID3042059
ChEMBL
CHEMBL3187370
ChEBI
CHEBI:87422
UNII
505AFM77VU
EC Number
203-380-8
Nikkaji
J3.243C

Properties

Computed structural properties

XLogP
2.6
Topological polar surface area
26.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
6
Heavy atoms
11

Experimental & physicochemical properties

LipidsFatty Acyls [FA] -> Fatty esters [FA07] -> Short fatty esters [FA0710]
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Isoamyl butyrate) -> IFRA transparency List
LogP3.250
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density0.861 - 0.866

Physicochemical properties

Melting point
-73 °C · -73 °C
Boiling point
184 · 184-185 °C (lit.)
Density
0.862 g/mL · 0.862 g/mL at 25 °C (lit.)
vapor density
5.45 · 5.45 (vs air)
vapor pressure
1.1 hPa · 1.1 hPa (20 °C)
FEMA
2060 · 2060 | ISOAMYL BUTYRATE

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H226 (98.6%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P273, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1927 reports by companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H226: Flammable liquid and vapor [Warning Flammable liquids]

Hazard information

Regulatory Information · 5 items

Chemical: Butanoic acid, 3-methylbutyl ester

Regulation (EC) No 1831/2003 (amended)

Butanoic acid, 3-methylbutyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Butanoic acid, 3-methylbutyl ester 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)

REACH registered substance: 3-methylbutyl butyrate (EC: 203-380-8)

Isoamyl butyrate: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Butanoic acid, 3-methylbutyl ester: Human health tier I assessment
Hazard Classes and Categories · 2 items

Flam. Liq. 3 (98.6%)

Flammable liquids - Category 3

Toxicology

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

PPE
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk
1
tsca
TSCA listed
rtecs
ET5034000
ridadr
UN 3272 3/PG 3
hs_code
29156019

Chemistry & industry

Pharmacology

Cellular LocationsExtracellular

Uses & manufacturing

U.S. Production2023: 16,129 lb
Consumer UsesFragrance
Household ProductsInformation on 16 consumer products that contain Isoamyl Butyrate in the following categories is provided:
Use Classification · 3 items

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing InformationButanoic acid, 3-methylbutyl ester: ACTIVE
Applications · 6 items

DescriptionIsoamyl Butyrate is a chemical ester of butyrate. It is a kind of flavoring agent that widely used in the preparation of a variety of fruit juice flavor, such as apricots, bananas, pears, apples and other flavor. It is high-demand flavor and fragrance compounds widely used in the food, beverage, cosmetic, and pharmaceutical industries. It is also a kind of solvent for extracting natural spices and the solvent of acetate fiber. Its synthesis can be mediated by the lipase (from various sources) catalyzed esterfication of isoamyl alcohol and butyrate.

DescriptionIsoamyl butyrate has a strong, characteristic, fruity (pear-like) odor and a sweet, corresponding taste. Usually prepared by esterification of commercial isoamyl alcohols with butyric acid by heating in the presence of TwitchelFs reagent; or by fermentation from butyric acid and isoamyl alcohol.

OccurrenceReported found in the oil of Eucalyptus macarthuri and in coconut oil. Also reported found in apple, apricot, banana, kumquat peel oil, guava, grapes, melon, strawberry, tomato, cheeses, beer, cognac, rum, Scotch whiskey, cider, grape wines, port, honey, yellow passion fruit, plum, mango, plum wine, cashew apple, cherimoya, bilberry wine, mountain papaya, Roman chamomile, mastic gum leaf and fruit oil.

UsesIsoamyl Butyrate is a synthetic flavoring agent that is a stable, col- orless liquid of strong fruity odor. it is usually prepared by esterifica- tion of isoamyl alcohols with butyric acid. it is soluble in most fixed oils and mineral oil and is insoluble in glycerin and propylene gly- col. storage should be in glass, tin, or resin-lined containers. it is used in fruit flavors such as pineapple, raspberry, and strawberry and has application in dessert gels, puddings, and baked goods at 50–60 ppm.

Usesmanufacture of artficial rum and fruit essences. Extensively used in flavor compositions. This ester may constitute a large percentage of many fruit flavors, such as: imitation Apricot, Banana, Cherry, Peach, Strawberry, "Tutti- -frutti", etc. and in Butter, Butterscotch, Chocolate, etc. Concentration in finished product may be 80 ppm in candy, and up to 550 ppm in chewing gum. Occasionally used to impart "lift" to perfumes and to modify "creamy" notes with Amyl phenylacetate, Vanillin, etc.

General DescriptionNatural occurrence: Melon, papaya, hop oil, grape brandy, bourbon whiskey, honey, jack fruit.

Preparation methods

PreparationUsually prepared by esterification of commercial isoamyl alcohols with butyric acid by heating in the presence of Twitchell’s reagent; or by fermentation from butyric acid and isoamyl alcohol

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]

Additional notes

DefinitionChEBI: The butanoate ester of isoamylol.

Related reactions

0 records

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Linked notes

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