gamma-Octalactone

Base Information

• Chemical Name: gamma-Octalactone
• CAS No.: 104-50-7
• Deprecated CAS: 57084-15-8
• Molecular Formula: C8H14O2
• Molecular Weight: 142.198
• Hs Code.: 29322090
• European Community (EC) Number: 203-208-1
• NSC Number: 26509,24270
• UNII: UHD6M52X0K
• DSSTox Substance ID: DTXSID1047609
• Nikkaji Number: J69.811C
• Wikipedia: %CE%93-Octalactone
• Wikidata: Q27291078
• RXCUI: 2043769
• Metabolomics Workbench ID: 4350
• ChEMBL ID: CHEMBL3559967
• Mol file: 104-50-7.mol

Synonyms:(R)-4-octanolide;4-octanolide

Chemical Property of gamma-Octalactone

Chemical Property:

• Appearance/Colour: Colorless to yellowish oily shape liquid
• Vapor Pressure: 0.0408mmHg at 25°C
• Melting Point: 91 °C(Solv: ethanol (64-17-5))
• Refractive Index: n20/D 1.444(lit.)
• Boiling Point: 239.124 °C at 760 mmHg
• Flash Point: 91.876 °C
• PSA: 26.30000
• Density: 0.981 g/cm³
• LogP: 1.88220
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: 5.6-8.096g/L at 20℃
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 142.099379685
• Heavy Atom Count: 10
• Complexity: 120

Purity/Quality:

99% ^*data from raw suppliers

4-Octanolide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 38
• Safety Statements: 26-37/39-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Lactones
• Canonical SMILES: CCCCC1CCC(=O)O1
• Description: y-Octalactone has a strong, fruity odor reminiscent of coconut with a very sweet taste. This substance may be prepared synthetically from epoxy-1,2-hexane and sodio-malonic ester; after saponification the oxyacid is extracted with ether and is lactonized.
• Uses: 4-Octanolide is one of the fine organic aerosol emitted from meat cooking operations that was examined by high-resolution gas chromatography. (Gamma)-Octalactone is a synthetic flavoring agent that is a stable, colorless to slightly yellow liquid of peach odor. It should be stored in glass or tin containers. It is used in flavors for peach with applications in baked goods, candy, and ice cream at 5–17 ppm.

Technology Process of gamma-Octalactone

There total 75 articles about gamma-Octalactone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

1-hexene (592-41-6,25067-06-5) + Iodoacetic acid (64-69-7) → gamma-octalactone (104-50-7)

Guidance literature:

With tris(bipyridine)ruthenium(II) dichloride hexahydrate; sodium L-ascorbate; In methanol; acetonitrile; at 20 ℃; for 14h; Sealed tube; Irradiation;

DOI:10.1021/acs.orglett.7b03256

Reference yield: 95.0%

1,4-octanediol (51916-47-3) → gamma-octalactone (104-50-7)

Guidance literature:

With aluminum oxide; sodium bromite; In acetonitrile; for 4h; Ambient temperature;

DOI:10.1246/cl.1994.53

Reference yield: 92.0%

tert-Butyl-(5-butyl-tetrahydro-furan-2-yloxy)-dimethyl-silane (126680-75-9,126680-76-0) → gamma-octalactone (104-50-7)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; In water; at -78 - 25 ℃;

DOI:10.1016/S0040-4039(01)80509-8

upstream raw materials:

4-oxo-4-thiophen-2-yl-butyric acid

trans-5-octenoic acid

6-hydroxyoctanoic acid

4,7-dioxooctanoic acid

Downstream raw materials:

C₁₄H₂₀O₂Se

1-Heptene

5-butyl-3-(phenylselanyl)oxolan-2-one

1-[5-butyl-2-oxo-3-(phenylselanyl)oxolan-3-yl]-4,4-bis-(phenylsulfanyl)butyl acetate

Refernces

• 1、 Troyanskii, E. I.,Svitan'ko, I. V.,Nikishin, G. I.. "DIRECT OXIDATION OF ALKANOIC ACIDS TO LACTONES". . p. 2041 - 2046. Retrieved 1982.
• 2、 Xie, Zhong-Yu,Deng, Jin,Fu, Yao. "W(OTf)6-Catalyzed Synthesis of Γ-Lactones by Ring Contraction of Macrolides or Ring Closing of Terminal Hydroxyfatty Acids in Ionic Liquid". . p. 2332 - 2339. Retrieved 2018.
• 3、 Nakano, Taichi,Kayama, Mikio,Nagai, Yoichiro. "Free Radical Addition of 2-Bromoalkanoic Acids to Alkenes". . p. 1049 - 1052. Retrieved 1987.
• 4、 Gavin,Geraghty. "A general synthesis of (+)-γ-substituted γ-butyrolactones using a kinetic alkylation-ozonolysis procedure". . p. 1351 - 1361. Retrieved 1994.
• 5、 Kabasakalian,Townley. "-". . p. 2711,2716. Retrieved 1962.
• 6、 Vinogradov, M. G.,Dolinko, V. I.,Nikishin, G. I.. "OXIDATIVE ADDITION OF 1,3-DICARBONYL COMPOUNDS TO OLEFINS BY THE ACTION OF THE Mn(OAc)3/LiCl SYSTEM AND THE SYNTHESIS OF FUNCTIONALLY SUBSTITUTED CYCLOPROPANES". . p. 334 - 341. Retrieved 1984.
• 7、 Triandafillidi, Ierasia,Kokotou, Maroula G.,Kokotos, Christoforos G.. "Photocatalytic Synthesis of γ-Lactones from Alkenes: High-Resolution Mass Spectrometry as a Tool to Study Photoredox Reactions". supporting information. p. 36 - 39. Retrieved 2018/01/17.