Grundinformationen
- Standard-SMILES
CC1CCC(=O)O1- InChIKey
GAEKPEKOJKCEMS-UHFFFAOYSA-N- Summenformel
- C5H8O2
- Durchschnittliche Molmasse
- 100,12 g/mol
- Monoisotopische Masse
- 100,0524295
Überblick
Gamma-valerolactone is a clear, colorless, mobile liquid. pH (anhydrous): 7.0. pH (10% solution in distilled water): 4.2. (NTP, 1992)
Namen und Bezeichner
- Bevorzugter Name
- Gamma-Valerolactone
- IUPAC
- 5-methyloxolan-2-one
- Lokaler Name
- γ-Valerolacton
- Englischer Name
- γ-Valerolactone
- Summenformel
- C5H8O2
- Molmasse
- 100.12
Namen und Synonyme
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
Weitere Namen anzeigen
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
Datenbank-Bezeichner
- 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
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,6
- Polarare Oberfläche (TPSA)
- 26,3 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 7
- Formalladung
- 0
- Komplexität
- 88,1
Experimentelle und physikochemische Eigenschaften
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)
Physikochemische Eigenschaften
- Schmelzpunkt
- 31 °C · −31 °C(lit.)
- Siedepunkt
- 207 · 207-208 °C(lit.)
- Dichte
- 1.05 g/mL · 1.05 g/mL at 25 °C(lit.)
- Dampfdichte
- 3.45 · 3.45 (vs air)
- Dampfdruck
- 30 · 30-44Pa at 20-25℃
- Brechungsindex
- 20 · n20/D 1.432(lit.)
- FEMA
- 3103 · 3103 | GAMMA-VALEROLACTONE
- Flammpunkt
- 204.8 °F · 204.8 °F
- storage temp.
- Sealed in dry,Room Temperature
- Löslichkeit
- Chloroform, Methanol
- Aggregatzustand
- Liquid
- Farbe
- Clear colorless
- PH
- 7 · 7 (H2O, 20℃)
- Geruch (Odor)
- 100 % · at 100.00 %. herbal sweet warm tobacco cocoa woody
- Geruchsart
- herbal
- Biologische Quelle
- synthetic
- Wasserlöslichkeit
- MISCIBLE
- JECFA Number
- 220 · 220
- BRN
- 80420 · 80420
- Dielectric constant
- 36.14 · 36.140000000000001
- Major Application
- flavors and fragrances
- Kosmetik-Inhaltsstoffe Funktionen
- 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 Datenbank
- 108 · 108-29-2(CAS DataBase Reference)
- NIST chemische Informationen
- 2 · 2(3H)-Furanone, dihydro-5-methyl-(108-29-2)
- EPA chemische Informationen
- 2 · 2(3H)-Furanone, dihydro-5-methyl- (108-29-2)
Sicherheit und Regulatorisches
GHS-Klassifizierung
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.
Gefahrenhinweise
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
Sicherheit und Schutzausrüstung
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)
Toxikologische Informationen
Adverse EffectsNeurotoxin - Acute solvent syndrome
Sicherheitsdaten
- wgk
- 2
- tsca
- TSCA listed
- hs_code
- 29322980
- RTECS-Nr.
- LU3580000
- risk_code
- 36-36/37/38
- hazard_code
- Xi
- safety_code
- 39-26-37/39
- Speicherklasse
- 10 - Combustible liquids
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2
Chemie und Industrie
Pharmakologische Informationen
Cellular LocationsCytoplasm
Verwendung und Herstellung
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
Anwendungen
Beschreibungγ-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.
Verwendenγ-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.
Darstellung
synthetischeBy reduction of levulinic acid followed by cyclization.
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