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Basic information
- CAS
104-50-7- Standard SMILES
CCCCC1CCC(=O)O1- InChIKey
IPBFYZQJXZJBFQ-UHFFFAOYSA-N- Molecular formula
- C8H14O2
- Average molar mass
- 142.2 g/mol
- Monoisotopic mass
- 142.09937969
Overview
Gamma-octalactone is a gamma-lactone that is oxolan-2-one substituted by a butyl group at position 5. It is a volatile compound found in peaches, mangoes, beef and ham. It has a role as an insect attractant, a flavouring agent, a mammalian metabolite, a mouse metabolite, a plant metabolite and a fungal metabolite. It is a volatile organic compound, a gamma-lactone and a tetrahydrofuranone.
Names & identifiers
- Preferred name
- gamma-Octalactone
- IUPAC
- 5-butyloxolan-2-one
- English name
- gamma-Octanoic lactone
- Molecular formula
- C8H14O2
- Molecular weight
- 142.2
Names & synonyms
GAMMA-OCTALACTONE104-50-74-Octanolide5-butyloxolan-2-one4-Hydroxyoctanoic acid lactone2(3H)-Furanone, 5-butyldihydro-5-Butyldihydro-2(3H)-furanone8-Oxo-5-octanolideOctanoic acid, gamma lactonegamma-Butyl-gamma-butyrolactonegamma-N-Butyl-gamma-butyrolactoneFEMA No. 2796
Show more names
γ-Octalactoneγ-OctalactoneΓ-OCTALACTONEγ-octanoic lactonegama-OctalactoneFEMA 2796
DTXSID1047609UHD6M52X0KNSC-24270NSC-26509DTXCID9027609CHEBI:145738RefChem:639598203-208-1
Database identifiers
- CAS
104-50-7- PubChem CID
- 7704
- DTXSID
DTXSID1047609- ChEMBL
CHEMBL3559967- ChEBI
CHEBI:145738- UNII
- UHD6M52X0K
Properties
Computed structural propertiesFilling in
- XLogP
- 1.6
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 120
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Lactones
LipidsFatty Acyls [FA] -> Fatty esters [FA07] -> Lactones [FA0704]
FragrancesFragrance Ingredient (gamma-Octalactone) -> IFRA transparency List
Food Additives
FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Food
Density0.970-0.980
Flavoring AgentsEU Flavoring substances
Solubility
slightly
soluble in alcohol and slightly soluble in water
(in ethanol)
Boiling Point
234.00 °C. @ 760.00 mm Hg
234 °C
Refractive Index1.443-1.447
Physical Description
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 92.8% (1616 of 1742) of all reports.
Not Classified
Aggregated GHS information provided per 1742 reports by companies from 9 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: 2(3H)-Furanone, 5-butyldihydro-
Regulation (EC) No 1831/2003 (amended)
2(3H)-Furanone, 5-butyldihydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2(3H)-Furanone, 5-butyldihydro- 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: 10-03-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/27548
2(3H)-Furanone, 5-butyldihydro-: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryA moderate skin irritant; [RTECS] Safe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; [Alfa Aesar MSDS] See Butyrolactone. See gamma-Nonalactone.
Hazard Classes and CategoriesNot Classified
Toxicology
Adverse EffectsNeurotoxin - Acute solvent syndrome
Safety data
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
UsesUsed as flavoring agent or adjuvant; [FDA]
U.S. Production2023: 7,000,000 - <8,500,000 lb
Consumer UsesFragrance
Industry UsesFragrance
Household ProductsInformation on 20 consumer products that contain Gamma-Octalactone in the following categories is provided:
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
General Manufacturing Information
All Other Chemical Product and Preparation Manufacturing
2(3H)-Furanone, 5-butyldihydro-: ACTIVE
Applications
Descriptiony-Octalactone has a strong, fruity odor reminiscent of coconut with a very sweet taste. This substance may be prepared synthetically from epoxy-1,2-hexane and sodio-malonic ester; after saponification the oxyacid is extracted with ether and is lactonized.
OccurrenceReported found in apricot, peach, blue cheese, butter, cooked chicken and cooked pork, licorice, milk, raspberry, roasted barley, and roasted filbert.
Uses4-Octanolide is one of the fine organic aerosol emitted from meat cooking operations that was examined by high-resolution gas chromatography.
Related reactions
3 records
Compound notes
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