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
Show more names
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
- Formal charge
- 0
- Complexity
- 108
Experimental & physicochemical properties
Solubility
118 mg/L @ 25 °C (exp)
Soluble in ethanol and most fixed oils, insoluble in glycerol, propylene glycol and water
1ml in 4ml 70% ethanol (in ethanol)
Boiling Point
179.00 °C. @ 760.00 mm Hg
179 °C
Physical Description
Liquid
Liquid
Colourless liquid with a fruity odour
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
- refractive index
- 20 · n20/D 1.411(lit.)
- FLAVIS Number
- 9.055 · 09.055 | 3-Methylbutyl butyrate
- Flash point
- 136 °F · 136 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 0.5 g/l · 0.5g/l
- form
- liquid
- color
- Colorless to Almost colorless
- Specific Gravity
- 0.866 · 0.866 (20/4℃)
- Odor
- 100 % · at 100.00 %. fruity green apricot pear banana
- Odor Type
- fruity
- biological source
- synthetic
- Water Solubility
- 184.7 mg/L · 184.7mg/L at 20℃
- Merck
- 14 · 14,5115
- JECFA Number
- 45 · 45
- Henry's Law Constant
- 1.1 · 1.1×10-2 mol/(m3Pa) at 25℃, Brockbank (2013)
- Dielectric constant
- 3.9 · 3.9(20℃)
- Major Application
- flavors and fragrances
- Cosmetics Ingredients Functions
- PERFUMING
- InChI
- 1S/C9H18O2/c1-4-5-9(10)11-7-6-8(2)3/h8H,4-7H2,1-3H3
- InChIKey
- PQLMXFQTAMDXIZ-UHFFFAOYSA-N
- SMILES
- CCCC(=O)OCCC(C)C
- LogP
- 3.99 at · 3.99 at 22.4℃
- CAS DataBase Reference
- 106 · 106-27-4(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- ISOAMYL BUTYRATE
- FDA 21 CFR
- 172.515 · 172.515
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 505 AFM77VU · 505AFM77VU
- NIST Chemistry Reference
- 3 · Butanoic acid, 3-methylbutyl ester(106-27-4)
- EPA Substance Registry System
- Isoamyl butyrate (106-27-4)
- UNSPSC Code
- 12352108 · 12352108
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02
- Signal word
- Warning
- Hazard statements
- 226 · H226-H412
- Precautionary statements
- 210 · P210-P233-P240-P241-P242-P273
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36/37/39-24/25
- RIDADR
- 3272 · UN 3272 3/PG 3
- WGK Germany
- 1 · 1
- RTECS
- 5034000 · ET5034000
- TSCA
- TSCA listed
- HazardClass
- 3 · 3
- PackingGroup
- III
- HS Code
- 29156019 · 29156019
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 3 Flam · Aquatic Chronic 3Flam. Liq. 3
- Toxicity
- 50 orally · LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 5000 mg/kg
- REACH Registrations
- Active
- Limited Quantities
- 5 L · 5.0 L (1.3 gallons) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
GHS Classification
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
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
Hazard Classes and Categories
Flam. Liq. 3 (98.6%)
Flammable liquids - Category 3
Toxicology
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
- Toxicity
- LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 5000 mg/kg
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS02
- hazard_code
- Xi
- safety_code
- 26-36/37/39-24/25
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- III
- Hazard statements
- H226-H412
- Limited Quantities
- 5.0 L (1.3 gallons) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Chronic 3Flam. Liq. 3
- Precautionary statements
- P210-P233-P240-P241-P242-P273
Chemistry & industry
Pharmacology
Uses & manufacturing
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Applications
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
Upstream & downstream products
Upstream raw materials
Suppliers50 total
Additional notes
DefinitionChEBI: The butanoate ester of isoamylol.
Related reactions
No reaction records under the current filter.
Linked notes
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