Gamma-Valerolactone
Basic information
- CAS
108-29-2- Standard SMILES
CC1CCC(=O)O1- InChIKey
GAEKPEKOJKCEMS-UHFFFAOYSA-N- Molecular formula
- C5H8O2
- Average molar mass
- 100.12 g/mol
- Monoisotopic mass
- 100.0524295
Overview
Gamma-valerolactone is a clear, colorless, mobile liquid. pH (anhydrous): 7.0. pH (10% solution in distilled water): 4.2. (NTP, 1992)
Names & identifiers
- Preferred name
- Gamma-Valerolactone
- IUPAC
- 5-methyloxolan-2-one
- English name
- γ-Valerolactone
- Molecular formula
- C5H8O2
- Molecular weight
- 100.12
Names & synonyms
gamma-Valerolactone108-29-24-Pentanolide4-Valerolactonegamma-Pentalactone4-Hydroxypentanoic acid lactone4-Hydroxyvaleric acid lactone2(3H)-Furanone, dihydro-5-methyl-4-Methyl-gamma-butyrolactonegamma-Methyl-gamma-butyrolactone4-Methyl-4-hydroxybutanoic acid lactoneDIHYDRO-5-METHYL-2(3H)-FURANONE
Show more names
5-Methyldihydrofuran-2(3H)-oneγ-PentalactoneFEMA 31035-methyl-dihydro-furan-2-oneγ-ValeroactoneG-VALEROLACTONE
5-Methyltetrahydro-2-furanoneFEMA No. 3103DTXSID00476185-Methyldihydro-2(3H)-furanoneValeric acid, 4-hydroxy-, gamma-lactonePentanoic acid, 4-hydroxy-, gamma-lactoneO7056XK37XDihydro-5-methylfuran-2(3H)-one
Database identifiers
- CAS
108-29-2、57129-69-8- PubChem CID
- 7921
- DTXSID
DTXSID0047618- ChEMBL
CHEMBL195593- ChEBI
CHEBI:48569- UNII
- O7056XK37X
- EC Number
- 203-569-5
- Nikkaji
- J5.072E
Properties
Computed structural properties
- XLogP
- 0.6
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 88.1
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Lactones
LipidsFatty Acyls [FA] -> Fatty esters [FA07] -> Lactones [FA0704]
FragrancesFragrance Ingredient (gamma-Valerolactone) -> IFRA transparency List
LogP-0.270
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density
1.057 at 68 °F (NTP, 1992) - Denser than water; will sink
1.047-1.054
Flavoring AgentsEU Flavoring substances
Solubility
greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)
miscible with alcohol, most fixed oils and water
(in ethanol)
Flash Point178 °F (NTP, 1992)
Boiling Point
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 96.7% (1420 of 1469) of all reports.
Not Classified
Aggregated GHS information provided per 1469 reports by companies from 9 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: 2(3H)-Furanone, dihydro-5-methyl-
Regulation (EC) No 1831/2003 (amended)
Status: Active Update: 15-10-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/33023
2(3H)-Furanone, dihydro-5-methyl-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 2(3H)-Furanone, dihydro-5-methyl-: Environment tier I assessment
DOT LabelFlammable Liquid
Fire HazardsThis chemical is combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and upper respiratory tract.
Hazards Summary
A mild skin irritant; Causes general anesthesia in oral lethal-dose studies of rabbits and rats; [RTECS] A skin, eye, mucous membrane, and upper respiratory tract irritant; [NTP] Safe when used as a flavoring agent in food; [JECFA] An irritant; [Alfa Aesar MSDS] See Butyrolactones.
Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
Uses
A metabolite of n-hexane; [ChemIDplus] Used as flavoring agent or adjuvant; [FDA] A constituent of crude polyligneous acid; Used in dye bathes (coupling agent), brake fluid, cutting oils, and as a solvent for adhesives, insecticides, and lacquers; [NTP]
Metal Machining [Category: Heat or Machine]
Household ProductsInformation on 2 consumer products that contain Gamma-Valerolactone in the following categories is provided:
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
General Manufacturing Information2(3H)-Furanone, dihydro-5-methyl-: ACTIVE
Applications
Descriptionγ-Valerolactone (Item No. 28240) is an analytical reference standard categorized as a prodrug form of γ-hydroxyvaleric acid (GHV; ). This product is intended for research and forensic applications.
OccurrenceReported found in boiled beef, beef fat, beer, cacao, Swiss cheese, ground and roasted coffee, roasted filberts, milk fat, dried mushroom, peach, roasted peanuts, heated pork fat, black tea and yogurt. Also reported found in peach, strawberry jam, tomato, wheaten bread, Gruyere cheese, heated butter, cooked beef, white wine, red wine, coffee and Bourbon vanilla.
UsesIt finds it application as a food additive that is used to improve the taste or odor of a food. It is also used as toiletry fragrances.
γ-Valerolactone is a naturally occurring chemical found in fruits and is frequently used as a food additive. It can be converted to liquid alkenes which can be used as transportation fuels. γ-Valerolactone is widely used in dye baths (coupling agent), brake fluids, cutting oils, and as solvent for adhesives, insecticides, and lacquers.
Related reactions
75 records
Compound notes
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