| Identification | More | [Name]
gamma-Valerolactone | [CAS]
108-29-2 | [Synonyms]
1，4-Valerolactone
4,5-DIHYDRO-5-METHYL-2 (3H)-FURANONE
4-HYDROXYPENTANOIC ACID LACTONE
4-HYDROXYVALERIC ACID G-LACTONE
4-PENTANOLIDE
4-VALEROLACTONE
FEMA 3103
GAMMA-METHYL-GAMMA-BUTYROLACTONE
GAMMA-PENTANOLACTONE
GAMMA-VALEROLACTONE
G-VALEROLACTONE
γ-Valerolactone
VALEROLACTONE, GAMMA-
(±)-5-Methyl-dihydro-furan-2-one
(R,S)-5-Methyl-dihydro-furan-2-one
2(3H)-Furanone,dihydro-5-methyl-
4-Hydroxyvaleric acid lactone
4-hydroxyvalericacidlactone
4-Methyl-gamma-butyrolactone
4-Valerolacetone | [EINECS(EC#)]
203-569-5 | [Molecular Formula]
C5H8O2 | [MDL Number]
MFCD00005400 | [Molecular Weight]
100.12 | [MOL File]
108-29-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Colorless liquid. Surface
tension 30 dynes/cm (25C), viscosity 2.18 cP
(25C), pH (anhydrous): 7. pH (10% solution in distilled
water): 4.2. Miscible with water and most
organic solvents, resins, waxes, etc.; slightly misciblewith
zein, beeswax, petrolatum | [Melting point ]
−31 °C(lit.)
| [Boiling point ]
207-208 °C(lit.)
| [density ]
1.05 g/mL at 25 °C(lit.)
| [vapor density ]
3.45 (vs air)
| [vapor pressure ]
30-44Pa at 20-25℃ | [FEMA ]
3103 | [refractive index ]
n20/D 1.432(lit.)
| [Fp ]
204.8 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform, Methanol | [form ]
Liquid | [color ]
Clear colorless | [Odor]
at 100.00 %. herbal sweet warm tobacco cocoa woody | [PH]
7 (H2O, 20℃) | [biological source]
synthetic | [Odor Type]
herbal | [Optical Rotation]
Consistent with structure | [Water Solubility ]
MISCIBLE | [JECFA Number]
220 | [BRN ]
80420 | [Dielectric constant]
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 | [Uses]
Dye baths (coupling agent), brake fluids, cutting
oils, and as solvent for adhesives, insecticides, and
lacquers. | [CAS DataBase Reference]
108-29-2(CAS DataBase Reference) | [NIST Chemistry Reference]
2(3H)-Furanone, dihydro-5-methyl-(108-29-2) | [EPA Substance Registry System]
2(3H)-Furanone, dihydro-5-methyl- (108-29-2) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319 | [Precautionary statements ]
P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313 | [Hazard Codes ]
Xi | [Risk Statements ]
R36:Irritating to the eyes. | [Safety Statements ]
S39:Wear eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
2
| [RTECS ]
LU3580000
| [TSCA ]
Yes | [REACH Registrations]
Active | [HS Code ]
29322980 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2 | [Safety Profile]
Moderately toxic by
ingestion. A skin irritant. Mutation data
reported. Combustible liquid when exposed
to heat or flame; can react with oxidizing
materials. To fight fire, use water, foam,
CO2, dry chemical. When heated to
decomposition it emits acrid smoke and
irritating fumes. |
| Hazard Information | Back Directory | [General Description]
Clear, colorless, mobile liquid. pH (anhydrous): 7.0. pH (10% solution in distilled water): 4.2. | [Reactivity Profile]
GAMMA-VALEROLACTONE(108-29-2) 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. . This chemical is incompatible with strong oxidizing agents. GAMMA-VALEROLACTONE(108-29-2) is also incompatible with strong acids, strong bases and strong reducing agents. . | [Air & Water Reactions]
Water soluble. | [Fire Hazard]
This chemical is combustible. | [Description]
γ-Valerolactone (Item No. 28240) is an analytical reference standard categorized as a prodrug form of γ-hydroxyvaleric acid (GHV; Item No. 28241).1 This product is intended for research and forensic applications. | [Chemical Properties]
Colorless liquid. Surface
tension 30 dynes/cm (25C), viscosity 2.18 cP
(25C), pH (anhydrous): 7. pH (10% solution in distilled
water): 4.2. Miscible with water and most
organic solvents, resins, waxes, etc.; slightly misciblewith
zein, beeswax, petrolatum; immiscible with anhydrous glycerin, glue, casein, arabic gum, and
soybean protein. Combustible. | [Chemical Properties]
γ-Valerolactone has a sweet, herbaceous odor. | [Occurrence]
Reported 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. | [Definition]
ChEBI: 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. | [Preparation]
By reduction of levulinic acid followed by cyclization. | [Synthesis Reference(s)]
Journal of the American Chemical Society, 112, p. 1286, 1990 DOI: 10.1021/ja00159a082
Tetrahedron Letters, 26, p. 5639, 1985 DOI: 10.1016/S0040-4039(01)80907-2
The Journal of Organic Chemistry, 50, p. 3930, 1985 DOI: 10.1021/jo00220a053 | [Biochem/physiol Actions]
Odor at 1% | [Purification Methods]
Purify the -lactone by repeated fractional distillation [Boorman & Linstead J Chem Soc 577, 580 1933]. IR: max 1790 (CS2), 1775 (CHCl3) cm-1 [Jones et al. Can J Chem 3 7 2007 1959]. The BF3-complex distils at 110-111o/20mm [Reppe et al. Justus Liebigs Ann Chem 596 179 1955]. It is characterized by conversion to -hydroxy-n-valeramide on treatment with NH3, m 51.5-52o (by slow evaporation of a CHCl3 solution). [Beilstein 17 H 235, 17 I 131, 17 II 288, 17 III/IV 4176, 17/9 V 24.] | [References]
[1] H ANDRESEN-STREICHERT. Uptake of gamma-valerolactone–detection of gamma-hydroxyvaleric acid in human urine samples.[J]. Journal of analytical toxicology, 2013, 37 4: 250-254. DOI: 10.1093/jat/bkt013 |
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