Dihydro-2-methyl-3(2H)-furanone

HCID 18522
NotesReactions
Substructure searchFind similar structures

Basic information

CAS
3188-00-9
Standard SMILES
CC1OCCC1=O
InChIKey
FCWYQRVIQDNGBI-UHFFFAOYSA-N
Molecular formula
C5H8O2
Average molar mass
100.12 g/mol
Monoisotopic mass
100.0524295

Overview

Dihydro-2-methyl-3(2H)-furanone is a member of oxolanes.

Names & identifiers

Preferred name
Dihydro-2-methyl-3(2H)-furanone
IUPAC
2-methyloxolan-3-one
English name
2-Methyltetrahydrofuran-3-one
Molecular formula
C5H8O2
Molecular weight
100.12

Names & synonyms

2-METHYLTETRAHYDROFURAN-3-ONE3188-00-93(2H)-Furanone, dihydro-2-methyl-Dihydro-2-methyl-3(2H)-furanoneDihydro-2-methyl-3-furanone2-Methyl-3-oxotetrahydrofuran2-Methyl-3-ketotetrahydrofuranFEMA No. 33732-Methyl-2H-furan-3-oneDTXSID9047677I3703CL967DTXCID7027677
Show more names
COFFEE FURANONEFEMA 3373Dihyro-2-methyl-3(2H)-furanoneBread KetoneNatural Bread Ketone
RefChem:88395221-685-42-Methyloxolan-3-one2-Methyltetrahydro-3-furanone2-Methyl tetrahydro-3-furanoneTetrahydro-2-methylfuran-3-one2-Methyl-4,5-dihydro-3(2H)-furanone2-Methyldihydrofuran-3(2H)-one

Database identifiers

CAS
3188-00-9
PubChem CID
18522
DTXSID
DTXSID9047677
ChEMBL
CHEMBL3188615
ChEBI
CHEBI:173339
UNII
I3703CL967
EC Number
221-685-4
Nikkaji
J75.503F

Properties

Computed structural properties

XLogP
0
Topological polar surface area
26.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
7

Experimental & physicochemical properties

FragrancesFragrance Ingredient (2-Methyltetrahydrofuran-3-one) -> IFRA transparency List
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density1.180-1.185
Flavoring AgentsEU Flavoring substances
Solubility · 3 items

slightly

Slightly soluble in oils

Soluble (in ethanol)

Boiling Point · 2 items

138.00 to 139.00 °C. @ 760.00 mm Hg

139 °C

Physicochemical properties

Boiling point
139 °C · 139 °C (lit.)
Density
1.034 g/mL · 1.034 g/mL at 25 °C (lit.)
refractive index
20 · n20/D 1.429(lit.)
FEMA
3373 · 3373 | 2-METHYLTETRAHYDROFURAN-3-ONE
FLAVIS Number
13.042 · 13.042 | 4,5-Dihydro-2-methylfuran-3(2H)-one
Flash point
103 °F · 103 °F

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1664 reports by companies from 6 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 4 items

Chemical: 3(2H)-Furanone, dihydro-2-methyl-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Status: Active Update: 12-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/26300

3(2H)-Furanone, dihydro-2-methyl-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesFlam. Liq. 3 (100%)

Safety data

F
3-9
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
rtecs
LU3579000
ridadr
UN 1224 3/PG 3

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

Use Classification · 4 items

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information3(2H)-Furanone, dihydro-2-methyl-: ACTIVE
Applications · 3 items

Description2-Methyltetrahydrofuran-3-one has a bread, buttery topnote. May be prepared by hydrolytic decarboxylation of 2-methyl-4-carbomethoxytetrahydrofuran- 3-one; by acid-catalyzed ring closure of p-alkoxy- diazoketones.

OccurrenceReported found as a constituent in coffee aroma; also as a volatile flavor component in roasted filbert nuts. Also reported found in guava, raisin, pineapple, onion, baked and fried potato, tomato, wheat bread, crispbread, smoked fish, cooked beef and pork, pork liver, rum, cocoa, coffee, peanuts, potato chips, passion fruit, beans, mushroom, tamarind, sweet potato, licorice, malt, dried bonito, cherimoya, okra and maté

Uses2-Methyltetrahydro-3-furanone has been employed as an quorum sensing inhibitor-molecule to investigate its effect on growth and biofilm formation in Hafnia alvei.

Preparation methods

PreparationBy hydrolytic decarboxylation of 2-methyl-4-carbomethoxytetrahydrofuran-3-one; by acid-catalyzed ring closure of β-alkoxy-diazoketones

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021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
枣庄九星生物科技有限公司0632-3759569 13589608009
INTATRADE GmbH+49 3493/605464 · [email protected]

Additional notes

DefinitionChEBI: Dihydro-2-methyl-3(2H)-furanone is a member of oxolanes.

Related reactions

9 records
New reaction record

Compound notes

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