63095-33-0

Basic information

• Product Name: (Z)-5-(3-hexenyl)dihydrofuran-2(3H)-one
• Synonyms: (Z)-5-(3-hexenyl)dihydrofuran-2(3H)-one;2(3H)-Furanone, 5-(3Z)-3-hexenyldihydro-;CIS-DEC-7-ENO-1,4-LACTONE;(z)-2(3h)-furanon;2(3H)-Furanone,5-(3-hexenyl)dihydro-,(Z)-;5-(3-hexenyl)dihydro-, (Z)-2(3H)-Furanone;4,5-Dihydro-5-[(Z)-3-hexenyl]furan-2(3H)-one;5-[(Z)-3-Hexenyl]dihydro-2(3H)-furanone
• CAS NO: 63095-33-0
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.23284
• EINECS: 263-852-4
• Mol File: 63095-33-0.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 279.1°C at 760 mmHg
• Flash Point: 111.9°C
• Appearance: /
• Density: 0.969g/cm³
• Vapor Pressure: 0.00409mmHg at 25°C
• Refractive Index: 1.466
• Storage Temp.: Amber Vial, Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: (Z)-5-(3-hexenyl)dihydrofuran-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-5-(3-hexenyl)dihydrofuran-2(3H)-one(63095-33-0)
• EPA Substance Registry System: (Z)-5-(3-hexenyl)dihydrofuran-2(3H)-one(63095-33-0)

Safety Data

• Hazardous Substances Data: 63095-33-0(Hazardous Substances Data)

Usage

Uses

(Z)-γ-Jasmolactone is a compound that has a fruity, flowery and sweet taste and is commonly used as a fruit flavouring agent to enhance the peach flavour in a variety of food items.

InChI:InChI=1/C10H16O2/c1-2-3-4-5-6-9-7-8-10(11)12-9/h3-4,9H,2,5-8H2,1H3/b4-3-

Upstream product

• 706-14-9 5-hexyldihydro-2(3H)-furanone 
• 125630-63-9 2-Methyl-2-dodecen-9-yn-6-one 
• 5009-31-4 (Z)-1-Bromohex-3-ene 
• 72049-83-3 (Z)-1-hydroxydec-7-en-4-one 
• 124909-23-5 (Z)-4-nitro-dec-7-enoic acid methylester 
• 98625-88-8 (Z)-1-nitrohept-4-ene 
• 79837-80-2 (Z)-7-bromo-3-heptene 
• 6191-71-5 (Z)-4-hepten-1-ol 
• 70553-34-3 diethyl 2-pentyl-3-oxoglutarate 
• 7011-82-7 methyl 4-oxodecanoate 
• 4144-54-1 4-oxodecanoic acid 
• 80709-20-2 methyl 4-oxodec-7-ynoate 
• 502-50-1 4-Ketopimelic acid 
• 6283-72-3 3-(5-oxotetrahydro-2-furanyl)propanoic acid 

Downstream Products

• 259675-66-6 Succinic acid mono-[(Z)-(S)-1-(2-benzylcarbamoyl-ethyl)-hept-4-enyl] ester 
• 67114-38-9 (S)-(-)-γ-jasmolactone 
• 155682-86-3 (R)-(+)-γ-jasmolactone 

Relevant articles and documents

Syntheses of methyl jasmonate and analogues

This account corresponds to the presentation given by the main author on the occasion of the 2nd Swiss Industrial Symposium in Basel (October 19th, 2018). After a short historical introduction to methyl-jasmonate and methyl-epijasmonate, it essentially focuses on the reported more promising industrial approaches devoted to the synthesis of these naturally occurring odorants isolated from jasmine flowers. Some attempts to simplify these approaches, as well as independent unreported strategies are also presented. Several asymmetric methodologies are also discussed such as Xie hydrogenation, Corey-CBS reduction, enzymatic resolution, and 1,4-addition.

Enantioselective synthesis of (-)-γ-jasmolactone

The title compound was prepared in seven steps starting from the commercially available 4-ketopimelic acid. The key step features an enantioselective lactonization promoted by PPL.

Hydroacylation of Alkyl Vinyl Ketones and Acrylic Esters Using Organotetracarbonylferrates. Synthesis of 1,4-Dicarbonyl Compounds

Alkyl vinyl ketones and acrylic esters were hydroacylated with organotetracarbonylferrates to the corresponding 1,4-diketones and 4-oxo carboxylic acid derivatives in good yield in dipolar aprotic solvents such as N,N-dimethylacetamide.Addition of 18-crown-6 improved the yield. cis-Jasmone and γ-jasmolactone were synthesized by use of these reactions.