Gamma-Valerolactone
GAMMA-VALEROLACTONE · 5-Methyldihydrofuran-2(3H)-one · Dihydro-5-methyl-2(3H)-furanone · γ-Pentalactone · 4-PENTANOLIDE · FEMA 3103 · 5-methyl-dihydro-furan-2-one · 4-HYDROXYPENTANOIC ACID LACTONE
Identifiers & Physical Properties
| CAS No. | 108-29-2 |
|---|---|
| Molecular formula | C5H8O2 |
| Average molar mass | 100.12 g/mol |
| Monoisotopic mass | 100.0524295 g/mol |
| SMILES | CC1CCC(=O)O1 |
| InChIKey | GAEKPEKOJKCEMS-UHFFFAOYSA-N |
| PubChem CID | 7921 |
| ChEMBL | CHEMBL195593 |
| ChEBI | CHEBI:48569 |
| EC No. | 203-569-5 |
| DTXSID | DTXSID0047618 |
Chemical & Physical Properties
| XLogP | 0.6 |
|---|---|
| Topological polar surface area | 26.3 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 0 |
| Heavy atoms | 7 |
| Formal charge | 0 |
| Complexity | 88.1 |
| Chemical classes | Other Classes -> Lactones |
| Lipids | Fatty Acyls [FA] -> Fatty esters [FA07] -> Lactones [FA0704] |
| Fragrances | Fragrance Ingredient (gamma-Valerolactone) -> IFRA transparency List |
| LogP (partition coefficient) | -0.270 |
| Food additives | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Density | 1.057 at 68 °F (NTP, 1992) - Denser than waterwill sink1.047-1.0541.05 g/mL at 25 °C(lit.) |
| Flavoring agents | EU 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)Chloroform, Methanol |
| Flash point | 178 °F (NTP, 1992)204.8 °F |
| Boiling point | 405 to 406 °F at 760 mmHg (NTP, 1992)207.00 to 208.00 °C. @ 760.00 mm Hg207 °C207-208 °C(lit.) |
| Melting point | -24 °F (NTP, 1992)-31 °C−31 °C(lit.) |
| Vapor density | 3.45 (NTP, 1992) - Heavier than airwill sink (Relative to Air)3.45 (vs air) |
| Vapor pressure | 30-44Pa at 20-25℃ |
| Refractive index | n20/D 1.432(lit.) |
| FEMA | 3103 | GAMMA-VALEROLACTONE |
| FLAVIS Number | 10.013 | Pentano-1,4-lactone |
| Storage conditions | Sealed in dry,Room Temperature |
| Physical state | Liquid |
| Color | Clear colorless |
| pH | 7 (H2O, 20℃) |
| Odor | at 100.00 %. herbal sweet warm tobacco cocoa woody |
| Odor type | herbal |
| Biological source | synthetic |
| optical activity | Consistent with structure |
| JECFA Number | 220 |
| BRN | 80420 |
| Dielectric constant | 36.140000000000001 |
| Major applications | 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 (partition coefficient) | -0.27 |
| CAS DataBase Reference | 108-29-2(CAS DataBase Reference) |
| Substances Added to Food (formerly EAFUS) | GAMMA-VALEROLACTONE |
| EWG's Food Scores | 1 |
| FDA UNII | O7056XK37X |
| 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) |
| UNSPSC Code | 85151701 |
| NACRES | NA.24 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319 |
| GHS precautionary statements | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313 |
| Hazard symbols | Xi |
| Risk statements (R) | 36-36/37/38 |
| Safety statements (S) | 39-26-37/39 |
| Water hazard class (WGK) | 2 |
| RTECS number | LU3580000 |
| TSCA inventory status | TSCA listed |
| Customs code | 29322980 |
| Storage class | 10 - Combustible liquids |
| Hazard class | Eye Irrit. 2Skin Irrit. 2 |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 96.7% (1420 of 1469) of all reports.Not ClassifiedAggregated GHS information provided per 1469 reports by companies from 9 notifications to the ECHA C&L Inventory. |
|---|---|
| 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/330232(3H)-Furanone, dihydro-5-methyl-: Does not have an individual approval but may be used under an appropriate group standard |
| Other safety information | IMAP assessments - 2(3H)-Furanone, dihydro-5-methyl-: Environment tier I assessment |
| DOT label | Flammable Liquid |
| Fire hazards | This chemical is combustible. (NTP, 1992) |
| Health hazards | SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and upper respiratory tract. |
| Hazards summary | A mild skin irritantCauses 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 group | Esters, 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 Reactions | Water soluble. |
| Hazard Classes and Categories | Not Classified |
| Fire fighting | Fires 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 Evacuation | Excerpt 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) |
| Adverse effects | Neurotoxin - Acute solvent syndrome |
| Water hazard class (WGK) | 2 |
| TSCA inventory status | TSCA listed |
| RTECS number | LU3580000 |
| Customs code | 29322980 |
| Risk statements (R) | 36-36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi |
| Safety statements (S) | 39-26-37/39 |
| Storage class | 10 - Combustible liquids |
| GHS hazard statements | H315-H319 |
| REACH registrations | Active |
| Hazard class | Eye Irrit. 2Skin Irrit. 2 |
| GHS precautionary statements | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313 |
Applications & Uses
Description
γ-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.
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.
Uses
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.
Uses
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.
Uses
γ-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 Description
γ-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 Description
γ-Valerolactone has been identified as one of the volatile flavor constituents in mango and honey.
Preparation & Synthesis
Preparation
By reduction of levulinic acid followed by cyclization.