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4-Hydroxy-2,5-dimethylfuran-3(2H)-one

Names

[ CAS No. ]:
3658-77-3

[ Name ]:
4-Hydroxy-2,5-dimethylfuran-3(2H)-one

[Synonym ]:
2,5-DiMethyl-4-hydroxy-3(2H)-furanone
CARMELAN
FEMA 3174
4-hydroxy-2,5-dimethyl-3-oxo-2H-furan
Pineapple ketone
4-Hydroxy-2,5-dimethylfuran-2(3H)-one
EINECS 222-908-8
T5OJ B1 CQ DQ E1
4-Hydroxy-2,5-dimethyl-3-furanone
Strawberry furanone
4-Hydroxy-2,5-dimethyl-3(2H)furanone
2,5-dimethyl-4-hydroxy-2H-furan-3-one
Dimethylhydroxy furanone
2,5-Dimethyl-4-hydroxy-3(2H)-furanone,Furaneol,Strawberry furanone
2,5-dimethyl-4-hydroxy-2,3-dihydrofuran-3-one
Alletone
Furaneol
4-Hydroxy-2,5-dimethylfuran-3(2H)-one
2,4-DIMETHYLBENZENEBORONIC ACID
T5O CV BHJ B1 DQ E1
4-oxo-3-hydroxy-2,5-dimethyl-4,5-dihydrofuran
HDMF
RI-2024
3(2H)-Furanone, 4-hydroxy-2,5-dimethyl-
4-Hydroxy-2,5-dimethyl-3(2H)-furanone
MFCD00010706
T5VV DOTJ C1 E1
COE 536

Biological Activity

[Description]:

Furaneol is mainly isolated from American grape (Vitis labrusca) and its hybrid grape. Furaneol is an important aroma compound in fruits and contribute to the strawberry-like note in some wines[1].

[Related Catalog]:

Research Areas >> Others
Signaling Pathways >> Others >> Others

[References]

[1]. Sasaki K, et al. Molecular cloning and characterization of UDP-glucose: furaneol glucosyltransferase gene from grapevine cultivar Muscat Bailey A (Vitis labrusca × V. vinifera. J Exp Bot. 2015 Oct;66(20):6167-74.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
215.5±40.0 °C at 760 mmHg

[ Melting Point ]:
73-77 °C(lit.)

[ Molecular Formula ]:
C6H8O3

[ Molecular Weight ]:
128.126

[ Flash Point ]:
90.5±20.8 °C

[ Exact Mass ]:
128.047348

[ PSA ]:
46.53000

[ LogP ]:
0.34

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.513

[ Storage condition ]:
2-8°C

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
LU3990000
CHEMICAL NAME :
3(2H)-Furanone, 2,5-dimethyl-4-hydroxy-
CAS REGISTRY NUMBER :
3658-77-3
LAST UPDATED :
199701
DATA ITEMS CITED :
8
MOLECULAR FORMULA :
C6-H8-O3
MOLECULAR WEIGHT :
128.14

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1608 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
Sister chromatid exchange

MUTATION DATA

TEST SYSTEM :
Rodent - mouse
DOSE/DURATION :
232 mg/kg
REFERENCE :
CHYCDW Zhonghua Yufangyixue Zazhi. Chinese Journal of Preventive Medicine. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) Beginning history not known. Volume(issue)/page/year: 22,85,1988

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;half-mask respirator (US);multi-purpose combination respirator cartridge (US)

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S36-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
LU3990000

[ HS Code ]:
2932190090

Synthetic Route

Precursor & DownStream

Customs

[ HS Code ]: 2932190090

[ Summary ]:
2932190090 other compounds containing an unfused furan ring (whether or not hydrogenated) in the structure VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:20.0%

Articles

Odorants in breast milk.

Arch. Pediatr. Adolesc. Med. 157(10) , 1031, (2003)

Structural basis for the enzymatic formation of the key strawberry flavor compound 4-hydroxy-2,5-dimethyl-3(2H)-furanone.

J. Biol. Chem. 288(23) , 16815-26, (2013)

The last step in the biosynthetic route to the key strawberry flavor compound 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF) is catalyzed by Fragaria x ananassa enone oxidoreductase (FaEO), earlier puta...

Characterization of the key aroma compounds in soy sauce using approaches of molecular sensory science.

J. Agric. Food Chem. 55(15) , 6262-9, (2007)

Application of aroma extract dilution analysis (AEDA) to the volatiles isolated from a commercial Japanese soy sauce revealed 30 odor-active compounds in the flavor dilution (FD) factor range of 8-409...


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