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Home> Encyclopedia >Antineoplastic Agents>Pharmaceutical Intermediates>Organic Intermediate
gamma-Valerolactone structure
gamma-Valerolactone structure


Iupac Name:5-methyloxolan-2-one
CAS No.: 108-29-2
Molecular Weight:100.11600
Modify Date.: 2022-11-29 11:41


Gamma-valerolactone is a clear, colorless, mobile liquid. pH (anhydrous): 7.0. pH (10% solution in distilled water): 4.2. (NTP, 1992)|Liquid|colourless to slightly yellow liquid with a warm, sweet, herbaceous odour

Gamma-valerolactone is a clear, colorless, mobile liquid. pH (anhydrous): 7.0. pH (10% solution in distilled water): 4.2. (NTP, 1992)|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.

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1. Names and Identifiers
1.1 Name
1.2 Synonyms

(±)-4-Methylbutyrolactone (±)-γ-Methylbutyrolactone (±)-γ-Pentalactone (±)-γ-Valerolactone (RS)-γ-Pentalactone 2(3H)-Furanone, dihydro-5-methyl- 4,5-Dihydro-5-methyl-2(3H)-furanone~4-Hydroxypentanoic acid lactone~gamma-Pentanolactone 4-Hydroxypentanoic acid lactone 4-Hydroxypentanoic acid γ-lactone 4-Hydroxyvaleric acid lactone 4-Methylbutyrolactone 4-Methyl-γ-butyrolactone 4-Pentanolide 5-Methyldihydro-2(3H)-furanone 5-Methyltetrahydro-2-furanone Dihydro-5-methyl-2(3H)-furanone Dihydro-5-methyl-2-furanone Dihydro-5-methylfuranone NSC 33700 Pentano-4-lactone Pentanoic acid, 4-hydroxy-, γ-lactone Tetrahydro-5-methyl-2-furanone Valeric acid, 4-hydroxy-, γ-lactone Valeric acid, γ-hydroxy-, lactone γ-Methylbutyrolactone γ-Methyl-γ-butyrolactone γ-Pentalactone γ-Valerolactone γ-VL

1.3 CAS No.
1.4 CID
1.6 Molecular Formula
C5H8O2 (isomer)
1.7 Inchi
1.8 InChkey
1.9 Canonical Smiles
1.10 Isomers Smiles
2. Properties
2.1 Density
2.1 Melting point
2.1 Boiling point
2.1 Refractive index
2.1 Flash Point
2.2 Precise Quality
2.2 PSA
2.2 logP
2.2 VaporDensity
3.45 (NTP, 1992) (Relative to Air)
2.3 Appearance
Gamma-valerolactone is a clear, colorless, mobile liquid. pH (anhydrous): 7.0. pH (10% solution in distilled water): 4.2. (NTP, 1992)
2.4 Storage
Ambient temperatures.
2.5 Chemical Properties
Colorless liquid. Surfacetension 30 dynes/cm (25C), viscosity 2.18 cP(25C), pH (anhydrous): 7. pH (10% solution in distilledwater): 4.2. Miscible with water and mostorganic solvents, resins, waxes, etc.; slightly misciblewithzein, beeswax, petrolatum; immiscible with anhydrous glycerin, glue, casein, arabic gum, andsoybean protein. Combustible.
2.6 Color/Form
Clear colorless
2.7 PH
7 (H2O, 20℃)
2.8 Water Solubility
Micible with water.
2.9 Stability
Stable at room temperature in closed containers under normal storage and handling conditions.
2.10 StorageTemp
Keep away from sources of ignition. Store in a cool, dry place. Store in a tightly closed container.
3. Use and Manufacturing
3.1 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.] gamma-Valerolactone Preparation Products And Raw materials Raw materials
3.2 Usage
Used in the perfume and flavor industries.
4. Safety and Handling
4.1 Hazard Codes
4.1 Risk Statements
4.1 Safety Statements
4.1 Packing Group
4.1 Hazard Declaration
4.1 Safety Profile
Moderately toxic byingestion. A skin irritant. Mutation datareported. Combustible liquid when exposedto heat or flame; can react with oxidizingmaterials. To fight fire, use water, foam,CO2, dry chemical. When heated todecomposition it emits acrid smoke andirritating fumes.
4.2 Caution Statement
P264, P280, P305+P351+P338, P33, P313
4.2 WGK Germany
4.2 Safety
Hazard Codes:Xi
Risk Statements:36
36:Irritating to the eyes
Safety Statements:39-26
39:Wear eye/face protection
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany:2
HS Code:29322980
4.3 Specification

Safety Statements:39-26
39:Wear eye/face protection
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s) No symbol.
Signal word

No signal word.

Hazard statement(s)


Precautionary statement(s)








2.3 Other hazards which do not result in classification


9. Other Information
9.0 Reactive Group
Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
9.1 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).
9.2 Fire Hazards
This chemical is combustible. (NTP, 1992)
9.3 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. STORAGE PRECAUTIONS: You should store this chemical at ambient temperatures, and keep it away from oxidizing materials. (NTP, 1992)
9.4 Personal Protective Equipment
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)
9.5 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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
9.6 Mesh Entry Terms
9.7 Manufacturing Info
2(3H)-Furanone, dihydro-5-methyl-: ACTIVE
9.8 Use Classification
Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Fatty Acyls [FA] -> Fatty esters [FA07] -> Lactones [FA0704]
9.9 Usage
It 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.
10. Computational chemical data
  • Molecular Weight: 100.11600g/mol
  • Molecular Formula: C5H8O2
  • Compound Is Canonicalized: True
  • XLogP3-AA: 0.6
  • Exact Mass: 100.052429494
  • Monoisotopic Mass: 100.052429494
  • Complexity: 88.1
  • Rotatable Bond Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Topological Polar Surface Area: 26.3
  • Heavy Atom Count: 7
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
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