gamma-Hexalactone
Basic information
- CAS
63357-95-9- Standard SMILES
CCC1CCC(=O)O1- InChIKey
JBFHTYHTHYHCDJ-UHFFFAOYSA-N- Molecular formula
- C6H10O2
- Average molar mass
- 114.14 g/mol
- Monoisotopic mass
- 114.06807956
Overview
Gamma-caprolactone is a gamma-lactone that is oxolan-2-one substituted by an ethyl group at position 5. It has a role as a human blood serum metabolite.
Names & identifiers
- Preferred name
- gamma-Hexalactone
- IUPAC
- 5-ethyloxolan-2-one
- English name
- 4-Hexanolide
- Molecular formula
- C6H10O2
- Molecular weight
- 114.14
Names & synonyms
gamma-Caprolactone695-06-7gamma-Hexalactone4-Hexanolidegamma-Hexanolactone6-CaprolactoneTonkalideToukalide2(3H)-Furanone, 5-ethyldihydro-Hexanolide-1,4Hexan-4-olide4-Ethyl-4-butanolide
Show more names
γ-HexalactoneFEMA 2556γ-Hexalactone5-Ethyldihydrofuran-2(3H)-oneDihydro-5-ethyl-2(3H)-furanone
gamma-Ethylbutyrolactone5-Ethyltetrahydro-2-furanone5-ETHYLDIHYDRO-2(3H)-FURANONEgamma-Ethyl-n-butyrolactoneFEMA No. 2556DTXSID8041298J16NAT1G41NSC-24255
Database identifiers
- CAS
63357-95-9、695-06-7- PubChem CID
- 12756
- DTXSID
DTXSID8041298- ChEMBL
CHEMBL192458- ChEBI
CHEBI:85235- UNII
- J16NAT1G41
- EC Number
- 211-778-8、804-070-0
- Nikkaji
- J45.665I
Properties
Computed structural properties
- XLogP
- 0.7
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 98.7
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Lactones
LipidsFatty Acyls [FA] -> Fatty esters [FA07] -> Lactones [FA0704]
FragrancesFragrance Ingredient (gamma-Hexalactone) -> IFRA transparency List
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density1.020-1.025
Flavoring AgentsEU Flavoring substances
Solubility
slightly
1 ml in 1 ml 95% alcohol (in ethanol)
Boiling Point
100.00 to 102.00 °C. @ 18.00 mm Hg
220 °C
Melting Point-18 °C
Refractive Index1.437-1.442
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 94.6% (1637 of 1731) of all reports.
Not Classified
Aggregated GHS information provided per 1731 reports by companies from 7 notifications to the ECHA C&L Inventory.
Warning
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)
Hazard information
Regulatory Information
Chemical: 2(3H)-Furanone, 5-ethyldihydro-
Regulation (EC) No 1831/2003 (amended)
Status: Active Update: 09-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/27467
4-Hexanolide: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryA mild skin irritant; [RTECS] Safe when used as a flavoring agent in food; [JECFA] A strong eye irritant; [Alfa Aesar MSDS] See Butyrolactone.
Hazard Classes and Categories
Not Classified
Eye Irrit. 2 (100%)
Toxicology
Adverse EffectsNeurotoxin - Acute solvent syndrome
Toxicity Summary
The existing information was reviewed by the independent Expert Panel for Fragrance Safety and supports the use of γ-Hexalactone as described in this fragrance ingredient safety assessment. Data from read-across analog γ-valerolactone show that γ-hexalactone is not expected to be genotoxic. Data for γ-hexalactone provide a calculated Margin of Exposure (MOE) greater than 100 for the repeated dose toxicity and developmental toxicity endpoints, and data for read-across analog γ-dodecalactone provide a calculated MOE greater than 100 for the fertility endpoint. Data from read-across analog 4-hydroxybutanoic acid lactone show that there are no safety concerns for γ-hexalactone for skin sensitization under the current declared levels of use. γ-hexalactone is not expected to be photoirritating/photoallergenic based on evaluation of the ultraviolet/visible (UV/Vis) spectra. The local respiratory toxicity endpoint was evaluated using the Threshold of Toxicological Concern (TTC) for a Cramer Class I material, and the exposure to γ-hexalactone is below the TTC.
Chemistry & industry
Uses & manufacturing
UsesPermitted for use as an inert ingredient in non-food pesticide products; [EPA] Used as flavoring agent or adjuvant; [FDA]
Household ProductsInformation on 2 consumer products that contain Gamma-Caprolactone in the following categories is provided:
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information2(3H)-Furanone, 5-ethyldihydro-: ACTIVE
Applications
Descriptiongamma-Hexalactone has a warm, powerful, herbaceous, sweet odor and a sweet, coumarin-caramel taste. May be prepared by reduction of sorbic acid using Zn, Sn, or SnCl2 and concentrated HCL in acetic acid solution at 85°C; from ethylene oxide and sodio-malonic ester; also from propyl alcohol and methylacrylate in the presence of di-tert-butyl peroxide.
OccurrenceReported found in apple juice, apricot, orange juice, guava, raisin, papaya, peach, pineapple, berries, asparagus, peas, potato, tomato, breads, cheeses, butter, milk, chicken fat, cooked beef, cooked pork, beer, cognac, grape wines, cocoa, tea, filberts, pecans, passion fruit, Japanese plum, beans, mushroom, starfruit, mango, dried fig, prickly pear, licorice, soursop, Cape gooseberry, nectarines, quince, pawpaw and other sources.
Usesγ-Hexalactone may be used as an analytical standard for the determination of the analyte in wine, fruits, biological samples, meat products, and e-cigarette refill solutions by various chromatography techniques.
Uses4-Hexanolide was used as curing agent for diglycidyl ether of bisphenol A with ytterbium triflate as an initiator.
γ-Caprolactone was used as curing agent for diglycidyl ether of bisphenol A with ytterbium triflate as an initiator.
Related reactions
1 records
Compound notes
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