| Identification | More | [Name]
alpha-Angelica lactone | [CAS]
591-12-8 | [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
5-METHYL-2(3H)-FURANONE
A-ANGELICALACTONE
A-ANGELIC LACTONE
ALPHA-ANGELICALACTONE
ANGELICALACTONE
FEMA 3293
2,3-Dihydro-5-methyl-2-furanone
3-Pentenoic acid, 4-hydroxy-, gamma-lactone
4-hydroxy-3-pentenoicacigamma-lactone
4-Hydroxypent-3-enoic acid lactone
4-hydroxypent-3-enoicacidlactone
5-methyl-2(3h)-furanon
5-Methyl-2(3H)-furanone (.alpha.-angelicalactone)
5-Methyl-3H-furan-2-one
5-Methylfuran-2(3H)-one | [EINECS(EC#)]
209-701-8 | [Molecular Formula]
C5H6O2 | [MDL Number]
MFCD00005375 | [Molecular Weight]
98.1 | [MOL File]
591-12-8.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless to straw yellow liquid | [Melting point ]
13-17 °C(lit.) | [Boiling point ]
55-56 °C12 mm Hg(lit.) | [density ]
1.092 g/mL at 25 °C(lit.)
| [FEMA ]
3293 | [refractive index ]
n20/D 1.448(lit.)
| [Fp ]
155 °F
| [storage temp. ]
2-8°C
| [solubility ]
Chloroform, Ethyl Acetate | [form ]
Oil | [pka]
pK1:4.3 (25°C) | [color ]
Clear Light Yellow | [Specific Gravity]
1.101.092 | [Odor]
at 10.00 % in dipropylene glycol. sweet solvent nutty tonka coumarin tobacco | [biological source]
synthetic | [Odor Type]
coconut | [Water Solubility ]
5 g/100 mL (25 ºC) | [JECFA Number]
221 | [Merck ]
14,647 | [BRN ]
108394 | [Major Application]
flavors and fragrances | [Cosmetics Ingredients Functions]
PERFUMING | [InChI]
1S/C5H6O2/c1-4-2-3-5(6)7-4/h2H,3H2,1H3 | [InChIKey]
QOTQFLOTGBBMEX-UHFFFAOYSA-N | [SMILES]
CC1=CCC(=O)O1 | [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]
591-12-8(EPA Substance) |
| Hazard Information | Back Directory | [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. | [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. | [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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