{"Abbreviation":"GVL","Aliases":["4-Pentanolide","4-Valerolactone","4-Hydroxypentanoic acid lactone","γ-Pentalactone","4-Hydroxyvaleric acid lactone","2(3H)-Furanone, dihydro-5-methyl-","4-Methyl-γ-butyrolactone","Pentanolide-1,4","γ-Valeryllactone","γ-Methyl-γ-butyrolactone"],"Boiling Point":"405 to 406 °F at 760 mmHg (NTP, 1992)","CAS":"108-29-2","ChEBI":"CHEBI:48569","ChEMBL":"CHEMBL195593","ChemicalClasses":["carboxylic acid"],"Chirality":"racemic","Classes":null,"Density":"1.057 at 68 °F (NTP, 1992) - Denser than water; will sink g/cm\u003csup\u003e3\u003c/sup\u003e","DrugClasses":[],"EINECS":"203-569-5","European Community (EC) Number":"203-569-5","Flash Point":"178 °F (NTP, 1992)","HMDB ID":"HMDB0033840","HeavyAtomCount":7,"IUPACName":"5-methyloxolan-2-one","InChI":"InChI=1S/C5H8O2/c1-4-2-3-5(6)7-4/h4H,2-3H2,1H3","InChIKey":"GAEKPEKOJKCEMS-UHFFFAOYSA-N","Melting Point":"-24 °F (NTP, 1992)","MolecularFormula":"C\u003csub\u003e5\u003c/sub\u003eH\u003csub\u003e8\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e","MolecularWeight":"100.12 g/mol","Opticalactivity":"( + / - )","Physical Description":"Gamma-valerolactone is a clear, colorless, mobile liquid. pH (anhydrous): 7.0. pH (10% solution in distilled water): 4.2. (NTP, 1992)","PrevSalts":[],"PubChemId":7921,"Record Description":["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.","gamma-Valerolactone has been reported in Fusarium poae, Nicotiana tabacum, and other organisms with data available.","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.","Wikipedia|List of designer drugs|Sedatives|GHB analogues"],"RefCount":3,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Gamma-Valerolactone","Name":"γ-Valerolactone","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q845530","Name":"γ-Valerolactone","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/7921","Name":"γ-Valerolactone","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL195593","Name":"γ-Valerolactone","Sub":false}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:48569","Name":"γ-Valerolactone","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=108-29-2","Name":"γ-Valerolactone","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0033840","Name":"γ-Valerolactone","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/O7056XK37X","Name":"γ-Valerolactone","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID0047618","Name":"γ-Valerolactone","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 7921, γ-Valerolactone. Accessed July 3, 2025. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/7921\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/7921\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. γ-Valerolactone. UNII: O7056XK37X. Global Substance Registration System. Accessed July 3, 2025. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/O7056XK37X\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/O7056XK37X\u003c/a\u003e"],"SMILES":"CC1CCC(=O)O1","Solubility":"greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)","StereoisomerRacemic":"(RS)-γ-Valerolactone","Stereoisomers":["(+)-γ-Valerolactone","(+)-γ-Valerolactone"],"StereoisomersUNII":["",""],"StoreUNII":["O7056XK37X"],"StructureBase64":"PHN2ZyB4bWxucz0iaHR0cDovL3d3dy53My5vcmcvMjAwMC9zdmciIHhtbG5zOnhsaW5rPSJodHRwOi8vd3d3LnczLm9yZy8xOTk5L3hsaW5rIiBoZWlnaHQ9IjI4LjIzOG1tIiB2ZXJzaW9uPSIxLjIiIHZpZXdCb3g9IjAgMCA1Ny4xMDYgMjguMjM4IiB3aWR0aD0iNTcuMTA2bW0iPgogICAgICAKICAgIDxkZXNjPkdlbmVyYXRlZCBieSB0aGUgQ2hlbWlzdHJ5IERldmVsb3BtZW50IEtpdCAoaHR0cDovL2dpdGh1Yi5jb20vY2RrKTwvZGVzYz4KICAgICAgCiAgICA8ZyBmaWxsPSIjRkYwRDBEIiBzdHJva2U9IiMwMDAwMDAiIHN0cm9rZS1saW5lY2FwPSJyb3VuZCIgc3Ryb2tlLWxpbmVqb2luPSJyb3VuZCIgc3Ryb2tlLXdpZHRoPSIuNyI+CiAgICAgICAgICAgIAogICAgICAgIDxyZWN0IGZpbGw9IiNGRkZGRkYiIGhlaWdodD0iMjkuMCIgc3Ryb2tlPSJub25lIiB3aWR0aD0iNTguMCIgeD0iLjAiIHk9Ii4wIi8+CiAgICAgICAgICAgIAogICAgICAgIDxnIGNsYXNzPSJtb2wiIGlkPSJtb2wxIj4KICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDxsaW5lIGNsYXNzPSJib25kIiBpZD0ibW9sMWJuZDEiIHgxPSI1Ni4wODMiIHgyPSI0Mi4xNzgiIHkxPSI0LjQ2NCIgeTI9IjEwLjcwMSIvPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPGxpbmUgY2xhc3M9ImJvbmQiIGlkPSJtb2wxYm5kMiIgeDE9IjQyLjE3OCIgeDI9IjM5LjA5OSIgeTE9IjEwLjcwMSIgeTI9IjI1LjU4MyIvPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPGxpbmUgY2xhc3M9ImJvbmQiIGlkPSJtb2wxYm5kMyIgeDE9IjM5LjA5OSIgeDI9IjIzLjg0NCIgeTE9IjI1LjU4MyIgeTI9IjI3LjIxNiIvPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPGxpbmUgY2xhc3M9ImJvbmQiIGlkPSJtb2wxYm5kNCIgeDE9IjIzLjg0NCIgeDI9IjE3LjcxOCIgeTE9IjI3LjIxNiIgeTI9IjEzLjIzOSIvPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPGcgY2xhc3M9ImJvbmQiIGlkPSJtb2wxYm5kNSI+CiAgICAgICAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICAgICAgPGxpbmUgeDE9IjE4LjMyMiIgeDI9IjYuMTkxIiB5MT0iMTQuNjE2IiB5Mj0iMTIuMDA2Ii8+CiAgICAgICAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICAgICAgPGxpbmUgeDE9IjE4LjgzNSIgeDI9IjYuNzA0IiB5MT0iMTIuMjMyIiB5Mj0iOS42MjIiLz4KICAgICAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICAgICAgPGxpbmUgY2xhc3M9ImhpIiBzdHJva2U9IiNGRjBEMEQiIHgxPSI2LjE5MDk5OTk5OTk5OTk5OSIgeDI9IjEyLjI1NjQ5OTk5OTk5OTk5OSIgeTE9IjEyLjAwNiIgeTI9IjEzLjMxMSIvPgogICAgICAgICAgICAgICAgPGxpbmUgY2xhc3M9ImhpIiBzdHJva2U9IiNGRjBEMEQiIHgxPSI2LjcwNDAwMDAwMDAwMDAwMSIgeDI9IjEyLjc2OTUiIHkxPSI5LjYyMiIgeTI9IjEwLjkyNyIvPgogICAgICAgICAgICA8L2c+CiAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICA8bGluZSBjbGFzcz0iYm9uZCIgaWQ9Im1vbDFibmQ2IiB4MT0iMTcuNzE4IiB4Mj0iMjYuMDgxIiB5MT0iMTMuMjM5IiB5Mj0iNS42OTUiLz4KICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDxsaW5lIGNsYXNzPSJib25kIiBpZD0ibW9sMWJuZDciIHgxPSI0Mi4xNzgiIHgyPSIzMi4yNTUiIHkxPSIxMC43MDEiIHkyPSI0Ljk3MiIvPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPHBhdGggY2xhc3M9ImF0b20iIGQ9Ik01LjA3OCAxMC4wM3EuMCAuNzU2IC0uMjU2IDEuMzI4cS0uMjU2IC41NjUgLS43NTYgLjg4MXEtLjUgLjMxNSAtMS4yNDQgLjMxNXEtLjc1NiAuMCAtMS4yNjIgLS4zMTVxLS41MDYgLS4zMTYgLS43NTYgLS44ODdxLS4yNDQgLS41NzIgLS4yNDQgLTEuMzM0cS4wIC0uNzUgLjI0NCAtMS4zMXEuMjUgLS41NjUgLjc1NiAtLjg4MXEuNTA2IC0uMzE1IDEuMjc0IC0uMzE1cS43MzIgLS4wIDEuMjMyIC4zMTVxLjUgLjMxIC43NTYgLjg3NXEuMjU2IC41NjYgLjI1NiAxLjMyOHpNMS4yMTUgMTAuMDNxLS4wIC45MjMgLjM4NyAxLjQ1OXEuMzkzIC41MjkgMS4yMiAuNTI5cS44NCAuMCAxLjIyMSAtLjUyOXEuMzg3IC0uNTM2IC4zODcgLTEuNDU5cS0uMCAtLjkyOSAtLjM4NyAtMS40NTNxLS4zODEgLS41MjMgLTEuMjA5IC0uNTIzcS0uODMzIC0uMCAtMS4yMjYgLjUyM3EtLjM5MyAuNTI0IC0uMzkzIDEuNDUzeiIgaWQ9Im1vbDFhdG02IiBzdHJva2U9Im5vbmUiLz4KICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDxwYXRoIGNsYXNzPSJhdG9tIiBkPSJNMzEuMjM5IDMuMDc4cS0uMCAuNzU2IC0uMjU2IDEuMzI4cS0uMjU2IC41NjUgLS43NTcgLjg4MXEtLjUgLjMxNSAtMS4yNDQgLjMxNXEtLjc1NiAuMCAtMS4yNjIgLS4zMTVxLS41MDYgLS4zMTYgLS43NTYgLS44ODdxLS4yNDQgLS41NzIgLS4yNDQgLTEuMzM0cS4wIC0uNzUgLjI0NCAtMS4zMDlxLjI1IC0uNTY2IC43NTYgLS44ODFxLjUwNiAtLjMxNiAxLjI3NCAtLjMxNnEuNzMyIC4wIDEuMjMyIC4zMTZxLjUwMSAuMzA5IC43NTcgLjg3NXEuMjU2IC41NjUgLjI1NiAxLjMyN3pNMjcuMzc1IDMuMDc4cS0uMCAuOTIzIC4zODcgMS40NTlxLjM5MyAuNTMgMS4yMiAuNTNxLjg0IC0uMCAxLjIyMSAtLjUzcS4zODcgLS41MzYgLjM4NyAtMS40NTlxLS4wIC0uOTI5IC0uMzg3IC0xLjQ1MnEtLjM4MSAtLjUyNCAtMS4yMDkgLS41MjRxLS44MzMgLS4wIC0xLjIyNiAuNTI0cS0uMzkzIC41MjMgLS4zOTMgMS40NTJ6IiBpZD0ibW9sMWF0bTciIHN0cm9rZT0ibm9uZSIvPgogICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDxsaW5lIGNsYXNzPSJoaSIgaWQ9Im1vbDFibmQ2IiBzdHJva2U9IiNGRjBEMEQiIHgxPSIyNi4wODEiIHgyPSIyMS44OTk1IiB5MT0iNS42OTUiIHkyPSI5LjQ2NyIvPgogICAgICAgICAgICA8bGluZSBjbGFzcz0iaGkiIGlkPSJtb2wxYm5kNyIgc3Ryb2tlPSIjRkYwRDBEIiB4MT0iMzIuMjU1IiB4Mj0iMzcuMjE2NDk5OTk5OTk5OTk2IiB5MT0iNC45NzIiIHkyPSI3LjgzNjUwMDAwMDAwMDAwMSIvPgogICAgICAgIDwvZz4KICAgICAgICAgIAogICAgPC9nPgogICAgCjwvc3ZnPgo=","Subjective Effects":null,"Title":"γ-Valerolactone","UNII":"O7056XK37X","Wikidata":"Q845530","Wikipedia":"Gamma-Valerolactone","XLogP":0.6}