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

4-HYDROXY-2,5-DIMETHYL-3(2H)-FURANONE · STRAWBERRY FURANONE · 2,5-DIMETHYL-4-HYDROXY-3(2H)-FURANONE · HDMF · 4-HYDROXY-2,5-DIMETHYLFURAN-3(2H)-ONE · 4-hydroxy-2,5-dimethylfuran-2(3H)-one · FEMA 3174 · 2,5-dimethyl-4-hydroxy-2H-furan-3-one

https://huagongshe.com/de/chemical/19309

Molekülstruktur von 4-Hydroxy-2,5-dimethylfuran-2(3H)-on

Identifikatoren & physikalische Daten

CAS No.	3658-77-3
Summenformel	C6H8O3
Durchschnittliche Molmasse	128,13 g/mol
Monoisotopische Masse	128,04734411 g/mol
SMILES	CC1=C(O)C(=O)C(C)O1
InChIKey	INAXVXBDKKUCGI-UHFFFAOYSA-N
PubChem CID	19309
ChEMBL	CHEMBL3186302
ChEBI	CHEBI:76247
EC No.	222-908-8
DTXSID	DTXSID0041517
Lokaler Name	4-Hydroxy-2,5-dimethylfuran-2(3H)-on

Chemische & physikalische Eigenschaften

XLogP	0,7
Polarare Oberfläche (TPSA)	46,5
H-Brücken-Donoren	1
H-Brücken-Akzeptoren	3
Frei drehbare Bindungen	0
Schwere Atome	9
Formalladung	0
Komplexität	181
LogP (Verteilungskoeffizient)	log Kow = 0.95 at 20 °C
Geruch	Relatively weak, nonspecific odordilute solutions develop a pineapple, strawberry-like odorOdor description at 0.01%: Sweet, slightly burnt brown caramellic, cotton candy with a savory nuance
Geschmack	Caramel flavorTaste description at 0.10-1.00 ppm: Sweet caramellic cooked meaty and fruity nuances
Color/Form	Beige powderColorless crystals
Löslichkeit	In water, 0.315 g/mL at 25 °CSoluble in oil and ethanolInsoluble in waterSoluble (in ethanol)Chloroform (Slightly), Methanol (Slightly)176g/L at 20℃
Siedepunkt	216 °C188 °C
Decomposition	When heated to decomposition it emits acrid smoke and irritating vapors.
Schmelzpunkt	77-79 °C77 - 78 °C73-77 °C(lit.)
Dampfdichte	3.3 (Air = 1)
Dampfdruck	0.008 mm Hg at 25 °C0.81Pa at 25℃
Henry-Konstante	Henry's Law constant = 1.5X10-5 atm-cu m/mole at 25 °C
Physical Description	LiquidSolidColourless to white solidFruity caramel or burnt pineapple aroma
Dichte	1.049 g/mL at 25 °C
Brechungsindex	n20/D 1.439
FEMA	3174 \| 4-HYDROXY-2,5-DIMETHYL-3(2H)-FURANONE
Flammpunkt	>230 °F
Lagerbedingungen	2-8°C
pKa (Säurekonstante)	9.62±0.40(Predicted)
Aggregatzustand	Solid
Farbe	White
Geruch	at 1.00 % in propylene glycol. sweet cotton candy caramel strawberry sugar
Geruchsart	caramellic
Biologische Quelle	synthetic
JECFA Number	1446
BRN	1281357
Stabilität	Light Sensitive, Temperature Sensitive
Hauptanwendungen	cleaning productscosmeticsflavors and fragrancesfood and beveragespersonal care
Kosmetik-Inhaltsstoffe Funktionen	TONICFRAGRANCE
InChI	1S/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3,8H,1-2H3
InChIKey	INAXVXBDKKUCGI-UHFFFAOYSA-N
SMILES	CC1OC(C)=C(O)C1=O
LogP (Verteilungskoeffizient)	0.95 at 20℃
CAS Datenbank	3658-77-3(CAS DataBase Reference)
NIST chemische Informationen	2,5-Dimethyl-4-hydroxy-3(2h)-furanone(3658-77-3)
EPA chemische Informationen	4-Hydroxy-2,5-dimethyl-3(2H)furanone (3658-77-3)

Sicherheit & Vorschriften

Toxic Combustion Products
GHS-Einstufung	This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1843) of reports.WarningH302 (28.5%): Harmful if swallowed [Warning Acute toxicity, oral]H317 (80.1%): May cause an allergic skin reaction [Warning Sensitization, Skin]H319 (71.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]P261, P264, P264+P265, P270, P272, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1843 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 1 of 1843 reports by companies.There are 15 notifications provided by 1842 of 1843 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Regulatorische Informationen	Chemical: 3(2H)-Furanone, 4-hydroxy-2,5-dimethyl-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)3(2H)-Furanone, 4-hydroxy-2,5-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 3(2H)-Furanone, 4-hydroxy-2,5-dimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 20-12-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/220153(2H)-Furanone, 4-hydroxy-2,5-dimethyl-: Does not have an individual approval but may be used under an appropriate group standard
Brandpotenzial	A flammable liquid.
Special Reports	WHO/JEFCAWHO Food Additives Series 54 (2006)[Available from, as of May 27, 2016: http://www.inchem.org/pages/jecfa.html]

Anwendungen & Verwendung

Beschreibung

Furaneol is a very important aroma chemical and is a key flavoring compound found in many kinds of fruits. It can be chemically formed through different carbohydrates during the Mainlard reaction. It can also be synthesized by yeast, bacteria and plants and play some physiological effects. Study has shown that it can suppress the phosphorylation of cAMP response element binding protein, underlying its potential role as an effective inhibitor of hyperpigmentation. It also has the potential to become an effective antimicrobial agent for human beings.

Occurrence

Reported found in guava, grapes, pineapple, raspberry, strawberry fruit and jam, rye bread, Swiss cheese, boiled beef, beer, cocoa, coffee, tea, filberts, almonds, oatmeal, Arctic bramble, yellow passion fruit, mango, shoyu, fermented soy sauce, litchi, malt and Cape gooseberry.

Verwenden

2,5-Dimethyl-4-hydroxy-3(2H)-furanone is a component of meat essence composition. 2,5-Dimethyl-4-hydroxy-3(2H)-furanone is used in the flavor and perfume industry due to its sweet strawberry aroma.

Herstellung & Synthese

synthetische

Furaneol can be prepared by cyclization of hexane-2,5-diol-3,4-dione in the presence of an acidic catalyst.The dione is the ozonization product of 2,5- hexynediol, which is obtained by ethynylation of acetaldehyde. In another process, a dialkyl -methyldiglycolate (formed from an alkyl lactate and an alkyl monochloroacetate) is reacted with dialkyl oxalate in the presence of a sodium alkoxide and dimethylformamide. The reaction product is cyclized, alkylated, hydrolyzed, and decarboxylated.In another process, a dialkyl -methyldiglycolate (formed from an alkyl lactate and an alkyl monochloroacetate) is reacted with dialkyl oxalate in the presence of a sodium alkoxide and dimethylformamide. The reaction product is cyclized, alkylated, hydrolyzed, and decarboxylated .