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alpha-Angelica lactone

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alpha-Angelica lactone Basic information

Product Name:
alpha-Angelica lactone
Synonyms:
  • 3-PENTEN-4-OLIDE
  • 4-HYDROXY-3-PENTANOIC ACID GAMMA-LACTONE
  • 4-HYDROXY-3-PENTENOIC ACID GAMMA-LACTONE
  • 4-HYDROXY-3-PENTENOIC ACID G-LACTONE
  • 4-HYDROXY-3-PENTENOIC ACID LACTONE
  • 2,3-Dihydro-5-methyl-2-furanone
  • 3-Pentenoic acid, 4-hydroxy-, gamma-lactone
  • 4-hydroxy-3-pentenoicacigamma-lactone
CAS:
591-12-8
MF:
C5H6O2
MW:
98.1
EINECS:
209-701-8
Product Categories:
  • Miscellaneous Natural Products
Mol File:
591-12-8.mol
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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)
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Safety Information

Safety Statements 
24/25
RIDADR 
NA 1993 / PGIII
WGK Germany 
2
RTECS 
LU5075000
10-21
TSCA 
Yes
HS Code 
29322090
Toxicity
LD50 orl-mus: 2800 mg/kg DCTODJ 3,249,80

MSDS

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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

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.

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