Basic information
- 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
405 to 406 °F at 760 mmHg (NTP, 1992)
207.00 to 208.00 °C. @ 760.00 mm Hg
207 °C
Melting Point
-24 °F (NTP, 1992)
-31 °C
Vapor Density3.45 (NTP, 1992) - Heavier than air; will sink (Relative to Air)
Physicochemical properties
- Melting point
- 31 °C · −31 °C(lit.)
- Boiling point
- 207 · 207-208 °C(lit.)
- Density
- 1.05 g/mL · 1.05 g/mL at 25 °C(lit.)
- vapor density
- 3.45 · 3.45 (vs air)
- vapor pressure
- 30 · 30-44Pa at 20-25℃
- refractive index
- 20 · n20/D 1.432(lit.)
- FEMA
- 3103 · 3103 | GAMMA-VALEROLACTONE
- FLAVIS Number
- 10.013 · 10.013 | Pentano-1,4-lactone
- Flash point
- 204.8 °F · 204.8 °F
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Chloroform, Methanol
- form
- Liquid
- color
- Clear colorless
- PH
- 7 · 7 (H2O, 20℃)
- Odor
- 100 % · at 100.00 %. herbal sweet warm tobacco cocoa woody
- Odor Type
- herbal
- biological source
- synthetic
- optical activity
- Consistent with structure
- Water Solubility
- MISCIBLE
- JECFA Number
- 220 · 220
- BRN
- 80420 · 80420
- Dielectric constant
- 36.14 · 36.140000000000001
- Major Application
- flavors and fragrances
- Cosmetics Ingredients Functions
- PERFUMING
- InChI
- 1S/C5H8O2/c1-4-2-3-5(6)7-4/h4H,2-3H2,1H3
- InChIKey
- GAEKPEKOJKCEMS-UHFFFAOYSA-N
- SMILES
- CC1CCC(=O)O1
- LogP
- -0.27 · -0.27
- CAS DataBase Reference
- 108 · 108-29-2(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- GAMMA-VALEROLACTONE
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 7056 XK37X · O7056XK37X
- NIST Chemistry Reference
- 2 · 2(3H)-Furanone, dihydro-5-methyl-(108-29-2)
- EPA Substance Registry System
- 2 · 2(3H)-Furanone, dihydro-5-methyl- (108-29-2)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319
- Precautionary statements
- 264 · P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36-36/37/38
- Safety Statements
- 39 · 39-26-37/39
- WGK Germany
- 2 · 2
- RTECS
- 3580000 · LU3580000
- TSCA
- TSCA listed
- HS Code
- 29322980 · 29322980
- Storage Class
- 10 · 10 - Combustible liquids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2
- REACH Registrations
- Active
Safety & regulation
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
Reactivity Profile
GAMMA-VALEROLACTONE is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. This chemical is incompatible with strong oxidizers. (NTP, 1992). This chemical is incompatible with strong oxidizing agents. It is also incompatible with strong acids, strong bases and strong reducing agents. (NTP, 1992).
Air and Water ReactionsWater soluble.
Hazard Classes and CategoriesNot Classified
Safety & protection
Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Isolation and EvacuationExcerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Toxicology
Adverse EffectsNeurotoxin - Acute solvent syndrome
Safety data
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- LU3580000
- hs_code
- 29322980
- risk_code
- 36-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 39-26-37/39
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H315-H319
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2
- Precautionary statements
- P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313
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.
Usesγ-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.
Usesγ-valerolactone(GVL) can be used as a green solvent: To transform lignocellulose into furfural using a solid acid catalyst, H-mordenite.To synthesize phosphatidylserine.
General Descriptionγ-Valerolactone(GVL) is a dipolar aprotic, bio-based, fully degradable, non-toxic green solvent and has been aligned with "Safer Solvent and Auxiliaries"," Use of Renewable Feedstocks and Design for Degradation".
General Descriptionγ-Valerolactone has been identified as one of the volatile flavor constituents in mango and honey.
Preparation methods
PreparationBy reduction of levulinic acid followed by cyclization.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers1 total
HONEST JOY HOLDINGS LIMITED[email protected]
Additional notes
DefinitionChEBI: Gamma-valerolactone is a butan-4-olide that is dihydrofuran-2(3H)-one substituted by a methyl group at position 5. It has been found in the urine samples of humans exposed to n-hexane. It has a role as a flavouring agent and a human xenobiotic metabolite.
Related reactions
75 records
Linked notes
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