Basic information
- CAS
591-12-8- Standard SMILES
CC1=CCC(=O)O1- InChIKey
QOTQFLOTGBBMEX-UHFFFAOYSA-N- Molecular formula
- C5H6O2
- Average molar mass
- 98.1 g/mol
- Monoisotopic mass
- 98.03677943
Overview
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.
Names & identifiers
- Preferred name
- alpha-Angelica lactone
- IUPAC
- 5-methyl-3H-furan-2-one
- English name
- alpha-Angelica lactone
- Molecular formula
- C5H6O2
- Molecular weight
- 98.1
Names & synonyms
alpha-Angelica lactone591-12-85-Methylfuran-2(3H)-onealpha-Angelicalactone5-Methyl-2(3H)-furanone5-methyl-3H-furan-2-one2(3H)-FURANONE, 5-METHYL-4-Hydroxypent-3-enoic acid lactone4-Hydroxy-3-pentenoic acid gamma-lactonedelta(2)-Angelica lactone.alpha.-Angelica lactonegamma-Methyl-beta,gamma-crotonolactone
Show more names
α-Angelica lactoneFEMA 3293ANGELICALACTONE3-PENTEN-4-OLIDEalpha-Angelica lactone 98%
a-Angelica lactonealpha-AngelicalactonUNII-29CRF6L9C5delta(sup 2)-Angelica lactoneCCRIS 3594DTXSID7047693.beta.,.gamma.-Angelica lactonea-angelicalactone
Database identifiers
- CAS
591-12-8- PubChem CID
- 11559
- DTXSID
DTXSID7047693- ChEMBL
CHEMBL478640- ChEBI
Properties
Computed structural properties
- XLogP
- 0.6
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 124
Experimental & physicochemical properties
SpringerMaterials PropertiesCoriolis coupling
Density1.084 (20 °C/20 °C)
Flavoring AgentsEU Flavoring substances
Solubility
soluble in alcohol, slightly soluble in water
(in ethanol)
Boiling Point167-170 °C
Refractive Index1.443-1.451
Physical Descriptionclear, light to dark yellow liquid with a sweet herbaceous odour reminiscent of tobacco
Physicochemical properties
- Melting point
- 13 · 13-17 °C(lit.)
- Boiling point
- 55 · 55-56 °C12 mm Hg(lit.)
- Density
- 1.092 g/mL · 1.092 g/mL at 25 °C(lit.)
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1560) of reports.
Warning
H317 (99.9%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1560 reports by companies from 5 notifications to the ECHA C&L Inventory.
Warning
Hazard information
Regulatory Information
Chemical: 2(3H)-Furanone, 5-methyl-
2(3H)-Furanone, 5-methyl-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 2(3H)-Furanone, 5-methyl-: Environment tier I assessment
Hazard Classes and Categories
Skin Sens. 1A (99.9%)
Flammable liquids - Category 4
Safety data
- F
- 10-21
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- LU5075000
- ridadr
- NA 1993 / PGIII
- hs_code
- 29322090
- Toxicity
- LD50 orl-mus: 2800 mg/kg DCTODJ 3,249,80
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Storage Class
- 10 - Combustible liquids
Chemistry & industry
Uses & manufacturing
Use Classification
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information2(3H)-Furanone, 5-methyl-: ACTIVE
Applications
OccurrenceReported found in grape, white bread, soy bean and licorice.
Usesalpha-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.
General Descriptionα-Angelica lactone, a cyclic lactone that occurs naturally in tobacco, is generally used in tobacco flavoring.
Preparation methods
PreparationBy dry distillation of levulinic acid
Upstream & downstream products
Downstream products
Suppliers100 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司
Related reactions
3 records
Compound notes
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