alpha-Angelica lactone
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
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)
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
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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