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Furaneol

Furaneol Structure
Furaneol structure
CAS No.
3658-77-3
Chemical Name:
Furaneol
Synonyms
4-HYDROXY-2,5-DIMETHYL-3(2H)-FURANONE;2,5-DIMETHYL-4-HYDROXY-3(2H)-FURANONE;HDMF;STRAWBERRY FURANONE;4-HYDROXY-2,5-DIMETHYLFURAN-3(2H)-ONE;Furaneo;Pineapple ketone;2,5-dimethyl-4-hydroxy-2H-furan-3-one;2,5-dimethyl-4-hydroxy-3(2H)-furanone (Furaneol);CARMELAN
CBNumber:
CB1205015
Molecular Formula:
C6H8O3
Molecular Weight:
128.13
MDL Number:
MFCD00010706
MOL File:
3658-77-3.mol
Last updated:2024-04-26 17:21:34
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Furaneol Properties

Melting point 73-77 °C(lit.)
Boiling point 188 °C
Density 1.049 g/mL at 25 °C
vapor pressure 0.81Pa at 25℃
refractive index n20/D 1.439
FEMA 3174 | 4-HYDROXY-2,5-DIMETHYL-3(2H)-FURANONE
Flash point >230 °F
storage temp. 2-8°C
solubility Chloroform (Slightly), Methanol (Slightly)
pka 9.62±0.40(Predicted)
color White
Odor at 1.00 % in propylene glycol. sweet cotton candy caramel strawberry sugar
Odor Type caramellic
Water Solubility 176g/L at 20℃
JECFA Number 1446
BRN 1281357
Stability Light Sensitive, Temperature Sensitive
InChIKey INAXVXBDKKUCGI-UHFFFAOYSA-N
LogP 0.95 at 20℃
CAS DataBase Reference 3658-77-3(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS) 4-HYDROXY-2,5-DIMETHYL-3(2H)-FURANONE
FDA UNII 20PI8YZP7A
NIST Chemistry Reference 2,5-Dimethyl-4-hydroxy-3(2h)-furanone(3658-77-3)
EPA Substance Registry System 4-Hydroxy-2,5-dimethyl-3(2H)furanone (3658-77-3)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS05,GHS07
Signal word  Danger
Hazard statements  H302-H314-H317
Precautionary statements  P260-P270-P280-P301+P312-P303+P361+P353-P305+P351+P338
Hazard Codes  Xn
Risk Statements  22
Safety Statements  36-24/25
WGK Germany  3
RTECS  LU3990000
F  10-23
HS Code  29321900
NFPA 704
1
1 0

Furaneol price More Price(32)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich W317454 4-Hydroxy-2,5-dimethyl-3(2H)-furanone natural, ≥98%, FG 3658-77-3 100g $223 2024-03-01 Buy
Sigma-Aldrich W317454 4-Hydroxy-2,5-dimethyl-3(2H)-furanone natural, ≥98%, FG 3658-77-3 1kg $1200 2024-03-01 Buy
Sigma-Aldrich W317403 4-Hydroxy-2,5-dimethyl-3(2H)-furanone ≥98%, FCC, FG 3658-77-3 100g $130 2024-03-01 Buy
Sigma-Aldrich W317403 4-Hydroxy-2,5-dimethyl-3(2H)-furanone ≥98%, FCC, FG 3658-77-3 1kg $787 2024-03-01 Buy
Sigma-Aldrich 44869 4-Hydroxy-2,5-dimethyl-3(2H)-furanone analytical standard 3658-77-3 100mg $175 2024-03-01 Buy
Product number Packaging Price Buy
W317454 100g $223 Buy
W317454 1kg $1200 Buy
W317403 100g $130 Buy
W317403 1kg $787 Buy
44869 100mg $175 Buy

Furaneol Chemical Properties,Uses,Production

Description

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.

Chemical Properties

4-Hydroxy-2,5-dimethyl-3(2H)-furanone has a fruity caramel or "burnt pineapple" aroma. May be synthesized from dimethyl- 3,4-dihyroxyfuran-2,5-dicarboxylate.

Chemical Properties

Furaneol has a sweet, fruity, strawberry, hot sugar, fruity caramel or “burnt pineapple” aroma.

Chemical Properties

Furaneol is a constituent of pineapple and strawberry aroma and is also found in other foods. It forms colorless crystals (mp 77–79°C) with a relatively weak, nonspecific odor. Dilute solutions develop a pineapple, strawberrylike odor.

Chemical Properties

white to light yellow crystal powde

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.

Uses

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.

Preparation

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 .

Definition

ChEBI: A member of the class of furans that is 2,5-dimethylfuran carrying additional oxo and hydroxy groups at positions 3 and 4 respectively. It has been found particularly in strawberries and other such fruits.

Aroma threshold values

Detection: 0.03 to 60 ppb; aroma characteristics at 0.1%: sweet, slightly burnt brown caramellic, cotton candy with a savory nuance

Taste threshold values

Taste characteristics at 0.10 to 1.0 ppm: sweet caramellic cooked meaty and fruity nuances

Synthesis Reference(s)

The Journal of Organic Chemistry, 57, p. 5023, 1992 DOI: 10.1021/jo00044a047
Synthesis, p. 377, 1987

General Description

4-Hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF, DMHF) is a caramel-like smelling compound, identified in Maillard reaction systems based on pentoses by GC-MS and GCMS/MS. Solubility data of DMHF in six different solvents over the temperature range from 283.15K to 313.15K under atmospheric pressure of 0.10 MPa has been examined by dynamic method. Separation of the enantiomers of DMHF by capillary electrophoretic method has been reported. Commercially it is synthesized from L-rhamnose. DMHF has been identified as acidic odorant in Thai premium fish sauce samples by aroma extract dilution analysis (AEDA). It is identified as key aroma compound in the distiller′s grains (DG) from wheat. It is reported as the main flavor compound in strawberries and its biosynthesis has been reported. HDMF has been found in various fruits such as pineapples strawberries and grapes, as well as in beef broth , roasted coffee, bread crust, roasted beef, roasted sesame seeds and stewed beef.

Flammability and Explosibility

Not classified

Trade name

Furaneol® (Firmenich).

Biochem/physiol Actions

Taste at 0.10 to 1.0 ppm

Synthesis

From dimethyl-3,4-dihydroxyfuran-2,5-dicarboxylate

References

Pickenhagen, Wilhelm, et al. "Estimation of 2,5-dimethyl-4-hydroxy-3(2H)-furanone (FURANEOLA®) in cultivated and wild strawberries, pineapples and mangoes." Journal of the Science of Food & Agriculture 32.11(2010):1132-1134.
Farine, Jean Pierre, et al. "4-Hydroxy-5-methyl-3(2H)-furanone and 4-Hydroxy-2,5-dimethyl-3(2H)-furanone, Two Components of the Male Sex Pheromone of Eurycotis floridana (Walker) (Insecta, Blattidae, Polyzosteriinae)." Bioscience Biotechnology & Biochemistry 57.12(2014):2026-2030.
Schwab, W. "Natural 4-hydroxy-2,5-dimethyl-3(2H)-furanone (Furaneol®). " Molecules 18.6(2013):6936-51.

Furaneol synthesis

74-83-9
68786-17-4
3658-77-3
Synthesis of Furaneol from Methyl bromide and 2-Furancarboxylic acid, 3,4-dihydroxy-5-methyl-, ethyl ester

Furaneol Preparation Products And Raw materials

Raw materials

Crotononitrile (pract) Ethyl lactate Propylene glycol 4-Hydroxy-5-methyl-3-furanone

Preparation Products

4-Methoxy-2,5-dimethyl-3(2H)-furanone

Furaneol Suppliers

Global( 477)Suppliers
Supplier Tel Email Country ProdList Advantage
career henan chemical co
+86-0371-86658258 sales@coreychem.com China 29914 58
Hebei Mojin Biotechnology Co., Ltd 		+8613288715578 sales@hbmojin.com China 12456 58
Hebei Yanxi Chemical Co., Ltd. 		+8617531190177 peter@yan-xi.com China 5993 58
Henan Bao Enluo International TradeCo.，LTD 		+86-17331933971 +86-17331933971 deasea125996@gmail.com China 2503 58
Shaanxi Haibo Biotechnology Co., Ltd 		+undefined18602966907 qinhe02@xaltbio.com China 1000 58
Henan Fengda Chemical Co., Ltd 		+86-371-86557731 +86-13613820652 info@fdachem.com China 7845 58
Capot Chemical Co.,Ltd. 		571-85586718 +8613336195806 sales@capotchem.com China 29797 60
Henan Tianfu Chemical Co.,Ltd. 		+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21691 55
Hangzhou FandaChem Co.,Ltd. 		008657128800458; +8615858145714 fandachem@gmail.com China 9348 55
Hefei TNJ Chemical Industry Co.,Ltd. 		+86-0551-65418679 +86-18949832763 info@tnjchem.com China 2989 55
Supplier Advantage
career henan chemical co
58
Hebei Mojin Biotechnology Co., Ltd 		58
Hebei Yanxi Chemical Co., Ltd. 		58
Henan Bao Enluo International TradeCo.，LTD 		58
Shaanxi Haibo Biotechnology Co., Ltd 		58
Henan Fengda Chemical Co., Ltd 		58
Capot Chemical Co.,Ltd. 		60
Henan Tianfu Chemical Co.,Ltd. 		55
Hangzhou FandaChem Co.,Ltd. 		55
Hefei TNJ Chemical Industry Co.,Ltd. 		55

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View Lastest Price from Furaneol manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
4-Hydroxy-2,5-dimethyl-3(2H)furanone pictures 2024-04-26 4-Hydroxy-2,5-dimethyl-3(2H)furanone
3658-77-3
 US $20.00 / kg 1kg 99.9% 200000kg Ouhuang Engineering Materials (Hubei) Co., Ltd
Furaneol pictures 2024-04-12 Furaneol
3658-77-3
 US $0.00 / kg 1kg 99% 2000ton Shaanxi Haibo Biotechnology Co., Ltd
Furaneol pictures 2023-12-23 Furaneol
3658-77-3
 US $50.00-1.00 / KG 1KG 99% g-kg-tons, free sample is available Henan Fengda Chemical Co., Ltd
  • Furaneol pictures
  • Furaneol
    3658-77-3
  • US $0.00 / kg
  • 99%
  • Shaanxi Haibo Biotechnology Co., Ltd
  • Furaneol pictures
  • Furaneol
    3658-77-3
  • US $50.00-1.00 / KG
  • 99%
  • Henan Fengda Chemical Co., Ltd

Furaneol Spectrum

Furaneol(3658-77-3)1HNMRFuraneol(3658-77-3)13CNMRFuraneol(3658-77-3)IR1Furaneol(3658-77-3)Raman

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FURANEOL HYDROXY DIMETHYL FURANONE 4-HYDROXY-2,5-DIMETHYL-FURAN-3-ONE 2,5-DIMETHYL-4-HYDROXY-2,3-DIHYDROFURAN-3-ONE 2,5-dimethyl-4-hydroxy-(2H)-furan-3-one (furaneol) 2,5-dimethyl-4-hydroxy-3(2h)-furanon 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF) 3(2H)-Furanone, 2,5-dimethyl-4-hydroxy- 3(2H)-Furanone, 4-hydroxy-2,5-dimethyl- 4-Hydroxy-2,5-dimethyl 4-Hydroxy-2,5-dimethyl-3(2H)-furfuran ketone 2,5-DIMETHYL-4-HYDROXY-3(2H)-FURANONE, 9 5% furaneol?,2,5-dimethyl-4-hydroxy-3[2H]-furanone 2,5-dimethyl-4-hydroxy-3(2h)-furanone solution 2,5-DIMETHYL-4-HYDROXY-3(2H)-FURANO 2,5-DIMETHYL-4-HYDROXY-3(2H)-FURANONE: (15% IN PROYLENE GLYCOL) 2,5-Dimethyl-4-hydroxy-3(2H)-furanone (15% in Propylene Glycol, ca. 1.2mol/L) 4-HYDROXY-2,5-DIMETHYL-3(2H) FURANONE NATURAL 20% IN P.G. 4-HYDROXY-2,5-DIMETHYL-3(2H)-FURANONE 20% IN P.G. 4-HYDROXY-2,5-DIMETHYL-3(2H)-FURANONE NATURAL 2,5-Dimethyl-4-hydroxy-3(2H)-furanone, Furaneol, Strawberry furanone 2,5-Dimethyl-4-hydroxyfuran-3(2H)-one 3-Hydroxy-2,5-dimethylfuran-4(5H)-one RI-2024 4-Hydroxy-2,5-dimethyl-3(2H)furanone[CAS No.:3658-77-3,FEMA.:3174] Furanone >=99.0% 4-hydroxy-2,5-diMethyl-2,3-dihydrofuran-3-one Furanone 4-Hydroxy-2,5-diMethyl-3(2H)furanone Furanone,Natural 4-Hydroxy-2,5-dimethyl-3(2H)-furan-3-one 4-hydroxy-2,5-dimethyl-3(2h)-furanon 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF) Furaneol 4-Hydroxy-2,5-dimethyl-3(2H)-furanone 4-Hydroxy-2,5-diMethyl-3(2H)-furanone >=99.0% (GC) Alletone COE 536 coe536 hydroxy-2,5-dimethyl-3(2H)-4-furanone (Furaneol) pineappleketone 4-Hydroxy-2,5-dimethyl-3(2H)-furanone solution 2,5-Dimethyl-4-hydroxy-(2H)-furan-3-on for synthesis 4-Hydroxy-2.5-Dimethyl-3(2h)-Furanone (Natural & Synthetic) 4-Hydroxy-2,5-dimethyl-3(2H)furanone CAS NO.3658-77-3 kf-wang(at)kf-chem.com Natural Furaneol Strawberry furanone / 4-hydroxy-2,5-dimethylfuran-3-one 4-Hydroxy-2 5-dimethyl-3(2H)furanone 2,5-Dimethyl-4-hydroxy-3(2H)-furanone (Technical Grade) 2,5-Dimethyl-4-hydroxy-3(2H)-furanone> Furaneol USP/EP/BP strawberry furanone solution Supply CAS: 3658-77-3 Strawberry one with Best Price TIANFU CHEM-- 4-Hydroxy-2,5-dimethyl-3(2H)furanone CARMELAN FEMA 3174 4-HYDROXY-2,5-DIMETHYL-3(2H)-FURANONE 4-HYDROXY-2,5-DIMETHYLFURAN-3(2H)-ONE 2,5-DIMETHYL-4-HYDROXY-3(2H)-FURANONE