Basic information
- CAS
27538-10-9- Standard SMILES
CCC1OC(C)=C(O)C1=O- InChIKey
GWCRPYGYVRXVLI-UHFFFAOYSA-N- Molecular formula
- C7H10O3
- Average molar mass
- 142.15 g/mol
- Monoisotopic mass
- 142.06299418
Overview
2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone is a member of the class of furans that is furan-3(2H)-one carrying additional ethyl, hydroxy and methyl substituents at positions 2, 4 and 5 respectively. A key aroma compound in soy sauce and fish sauce. It has a role as a Saccharomyces cerevisiae metabolite. It is a member of furans, an enol and a cyclic ketone.
Names & identifiers
- Preferred name
- Homofuraneol
- IUPAC
- 2-ethyl-4-hydroxy-5-methylfuran-3-one
- English name
- Ethyl furaneol
- Molecular formula
- C7H10O3
- Molecular weight
- 142.15
Names & synonyms
27538-10-92-Ethyl-4-hydroxy-5-methyl-3(2H)-furanonehomofuraneol3(2H)-FURANONE, 2-ETHYL-4-HYDROXY-5-METHYL-2-ethyl-4-hydroxy-5-methylfuran-3-oneFEMA NO. 3623, 2-ETHYL-CHEBI:137995DTXSID40885393RefChem:471818DTXCID2010247762-Ethyl-4-hydroxy-5-methylfuran-3(2H)-oneEthyl furaneol
Show more names
FEMA 36234-Hydroxy-5-methyl-2-propyl-3(2H)-furanone4-HEMFRI-2056SUGAR FURANONE
Homofureanol4-Hydroxy-2-ethyl-5-methyl-3(2H)-furanoneHEMFMFCD00191360VRF4YF0C3X2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone (homofuraneol)CCRIS 6903EINECS 248-514-6
Database identifiers
- CAS
27538-10-9- PubChem CID
- 33931
- DTXSID
DTXSID40885393- ChEBI
CHEBI:137995- UNII
- VRF4YF0C3X
- EC Number
Properties
Computed structural properties
- XLogP
- 1.2
- Topological polar surface area
- 46.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 193
Experimental & physicochemical properties
FragrancesFragrance Ingredient (2-Ethyl-4-hydroxy-5-methylfuran-3(2H)-one) -> IFRA transparency List
Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Boiling Point103.00 °C. @ 15.00 mm Hg
Physicochemical properties
- Boiling point
- 248 · 248-249 °C(lit.)
- Density
- 1.137 g/mL · 1.137 g/mL at 25 °C(lit.)
- vapor pressure
- 78 · 78-89hPa at 20-40℃
- refractive index
- 20 · n20/D 1.512(lit.)
- FEMA
- 3623 · 3623 | 2-ETHYL-4-HYDROXY-5-METHYL-3(2H)-FURANONE
- Flash point
- 184 °F · 184 °F
- storage temp.
- 2 · under inert gas (nitrogen or Argon) at 2-8°C
- pka
- 9.62 · 9.62±0.40(Predicted)
- form
- Liquid
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 14.5% (80 of 550) of reports.
Warning
H302 (85.5%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 550 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 3(2H)-Furanone, 2-ethyl-4-hydroxy-5-methyl-
REACH registered substance: 2-ethyl-4-hydroxy-5-methylfuran-3(2H)-one (EC: 248-514-6)
Other Safety InformationIMAP assessments - 3(2H)-Furanone, 2-ethyl-4-hydroxy-5-methyl-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (85.5%)
Safety data
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- LU4250000
- hs_code
- 2932190090
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 23-36
- Hazard statements
- H302
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
Household ProductsInformation on 5 consumer products that contain 2-Ethyl-4-Hydroxy-5-Methylfuran-3(2h)-One in the following categories is provided:
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information3(2H)-Furanone, 2-ethyl-4-hydroxy-5-methyl-: ACTIVE
Applications
OccurrenceReported found in soy sauce, Swiss cheese and melon, coffee, shoyu, strawberry and pineapple.
Preparation methods
PreparationOne commercially applied synthesis is the condensation of 2-pentene nitrile with ethyl lactate followed by oxidation of the intermediate 4-cyano-5-ethyl-2-methyldihydro-3(2H)-furanone with monoperoxysulfate.
Suppliers80 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021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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