2(5H)-Furanone Property

Melting point:

4-5 °C (lit.)

Boiling point:

86-87 °C/12 mmHg (lit.)

Density 

1.185 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.469(lit.)

FEMA 

4138 | 4-HYDROXY-2-BUTENOIC ACID GAMMA-LACTONE

Flash point:

214 °F

storage temp. 

2-8°C

solubility 

Chloroform, Ethyl Acetate (Slightly)

form 

Liquid

color 

Clear colorless to pale yellow or amber

Odor

buttery

Odor Type

buttery

Water Solubility 

Immiscible with water.

JECFA Number

2000

BRN 

383585

Stability:

Moisture Sensitive

InChIKey

VIHAEDVKXSOUAT-UHFFFAOYSA-N

LogP

-0.600

CAS DataBase Reference

497-23-4(CAS DataBase Reference)

NIST Chemistry Reference

2(5H)-Furanone(497-23-4)

EPA Substance Registry System

2(5H)-Furanone (497-23-4)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

RTECS 

LU3453000

F 

8-10

Hazard Note 

Irritant

HS Code 

29322980

Hazardous Substances Data

497-23-4(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

2(5H)-Furanone Chemical Properties,Usage,Production

Chemical Properties

Colorless to pale brown-yellow clear liquid

Chemical Properties

2(5H)-Furanone is light brown liquid

Occurrence

Reported found in coffee

Uses

2(5H)-Furanone is employed in the preparation of 5-substituted 2(5H) furanones (gamma-butenolides) catalyzed by bifunctional aminothiourea and aminosquaramide organocatalysts through direct aldol reaction with aromatic aldehydes. Further, it is used in the synthesis of lignans by Michael addition reactions. In addition to this, it is used in three-component Michael-Aldol reactions with an aldehyde and thiolate or carbanion.

Uses

2(5H)-Furanone is a heterocyclic organic compound that is used widely in the synthetic preparation of pharmaceutical goods.

Uses

2(5H)-Furanone is a versatile reagent used in Michael addition reactions1 for synthesis of lignans.2 Also employed in three-component Michael-Aldol reactions with an aldehyde anda thiolate3 or carbanion.4

Definition

2(5H)-Furanone is a mycotoxin that contains an α,β-unsaturated lactone moiety.

General Description

Chiral urea compounds catalyzed hetero-Michael addition reaction of 2(5H)-furanone (γ-crotonolactone) to pyrrolidine. The quorum sensing inhibition activity by 2(5H)-furanone was studied using bioindicator strains.

Hazard

Extremely toxic.

Purification Methods

Fractionally distil the lactone under reduced pressure. IR: (CCl4) 1784 and 1742 cm-1, UV no max above 205nm ( 1160 cm-1 M-1) and 1HR: (CCl3) : 2.15 (pair of triplets 1H), 3.85 (pair of triplets 1H) and 5.03 (triplet 2H). [Price & Judge Org Synth Coll Vol V 255 1973, Smith & Jones Can J Chem 37 2007, 2092 1959, Beilstein 17/9 V 112.]