alpha-Angelica lactone Chemical Properties

Melting point:

13-17 °C(lit.)

Boiling point:

55-56 °C12 mm Hg(lit.)

Density 

1.092 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.448(lit.)

FEMA 

3293 | 4-HYDROXY-3-PENTENOIC ACID LACTONE

Flash point:

155 °F

storage temp. 

2-8°C

solubility 

Chloroform, Ethyl Acetate

form 

Oil

pka

pK1:4.3 (25°C)

Specific Gravity

1.101.092

color 

Clear Light Yellow

Odor

at 10.00 % in dipropylene glycol. sweet solvent nutty tonka coumarin tobacco

Odor Type

coconut

Water Solubility 

5 g/100 mL (25 ºC)

JECFA Number

221

Merck 

14,647

BRN 

108394

LogP

0.84

CAS DataBase Reference

591-12-8(CAS DataBase Reference)

NIST Chemistry Reference

2(3H)-Furanone, 5-methyl-(591-12-8)

EPA Substance Registry System

5-Methyl-2(3H)-furanone (591-12-8)

Safety Information

Safety Statements 

24/25

RIDADR 

NA 1993 / PGIII

WGK Germany 

2

RTECS 

LU5075000

F 

10-21

TSCA 

Yes

HS Code 

29322090

Toxicity

LD50 orl-mus: 2800 mg/kg DCTODJ 3,249,80

MSDS

• Language:English Provider:alpha-Angelica lactone
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

alpha-Angelica lactone Usage And Synthesis

Chemical Properties

clear colorless to straw yellow liquid

Chemical Properties

α-Angelica lactone has a sweet, herbaceous odor reminiscent of tobacco.

Occurrence

Reported found in grape, white bread, soy bean and licorice.

Uses

alpha-Angelicalactone acts as acancer chemopreventive agent. It is used in the synthesis of glutathione and the activity of glutathione-S-transferase and UDP-glucunonosyltransferase detoxification enzymes in esophagus, stomach, intestine, and liver. It is used in oral care formulations to round out mint notes and in coffee flavors.

Definition

ChEBI: Alpha-angelica lactone is an angelica lactone and a butenolide. It is functionally related to a but-3-en-4-olide. It is a tautomer of a beta-angelica lactone.

Preparation

By dry distillation of levulinic acid

Application

alpha-Angelica lactone finds occasional use in the reconstitution of essential oils. lts intensely sweet-herbaceous, almost tobacco-like odor makes this chemical interesting for application in new fragrance types. However, it would be wise to investigate its pharmacological and dermatological properties first.

Taste threshold values

Taste characteristics at 100 ppm: sweet, creamy, coconut, vanilla hay and coumarin-like nuances

General Description

α-Angelica lactone, a cyclic lactone that occurs naturally in tobacco, is generally used in tobacco flavoring.

Biochem/physiol Actions

Plant-derived cancer chemopreventive agent. Increases the synthesis of glutathione and the activity of glutathione-S-transferase and UDP-glucunonosyltransferase detoxification enzymes in esophagus, stomach, intestine, and liver.

Safety Profile

Moderately toxic by ingestion andintraperitoneal routes. When heated to decomposition itemits acrid smoke and irritating fumes.

alpha-Angelica lactone(591-12-8)Related Product Information

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