Furaneol

Structural formula
Basic structural formula (stereocenter is marked with an * )
General
Surname	Furaneol
other names	4-hydroxy-2,5-dimethyl-3 (2 H ) -furanone Alleton Strawberry furanone HD3F DIMETHYLHYDROXY FURANONE ( INCI )
Molecular formula	C 6 H 8 O 3
Brief description	white to yellowish solid
External identifiers / databases
CAS number 3658-77-3 EC number 222-908-8 ECHA InfoCard 100.020.826 PubChem 19309 ChemSpider 18218 Wikidata Q250455
properties
Molar mass	128.13 g mol −1
Physical state	firmly
Melting point	73-77 ° C
boiling point	215.5 ° C
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 302 P: no P-phrases
Toxicological data	1608 mg kg −1 ( LD 50 ,  mouse ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Furaneol is a naturally occurring chemical compound from the group of furanones . The name is a registered trademark of Firmenich SA Geneva .

Occurrence

strawberry

Furaneol occurs naturally in strawberries and a variety of other fruits. It is partly responsible for the smell of fresh pineapple . It is also important for the smell of buckwheat and tomatoes .

Extraction and presentation

Various reactions are known for the synthesis of furaneol.

It was first used in 1963 by Hodge et al. synthesized by a Maillard reaction of rhamnose with piperidine acetate and also detected in pineapple by Rodin in 1965.

It can also be obtained in low yield by a five-step reaction starting from tartaric acid . The decisive intermediate step is the formation of (4 R , 5 R ) -4,5-diacetyl-2,2-dimethyl-1,3-dioxolane by reacting methyl magnesium chloride with the corresponding 4,5-bis (dimethylamide).

The synthesis by electrohalogenation of a protected hexynediol (for example 3-hexyne-2,5-diol ) in a three-stage reaction with 39 percent yield or the cyclization of hexadione systems (for example hexane-3,4-dione ) is also possible.

Also possible is the biotechnological representation based on fructose-1,6-bisphosphate , which is based on a reaction scheme that is strongly based on glycolysis .

The biosynthesis in strawberries begins with 6-deoxyfructose via furaneol glycoside to furaneol.

Stereochemistry

It occurs in two enantiomeric forms as (+) - (2 R ) -Furaneol and (-) - (2 S ) -Furaneol, the odor mainly emanating from the ( R ) -form.

Furaneol (2 enantiomers)
( S ) configuration	( R ) configuration

properties

The substance is a white to yellowish solid which is sensitive to oxidation and heat. Its aroma is multi-faceted and changes from fruity in strong dilution to caramel-like to roasted in higher concentrations.

use

Furaneol is used as a flavoring agent. Its low odor threshold (nasal: 150 µg / kg, retronasal: 30 µg / kg water) owes its use in the food industry as a flavor component and flavor enhancer for baked goods.

Individual evidence

1. ↑ Entry on DIMETHYLHYDROXY FURANONE in the CosIng database of the EU Commission, accessed on March 21, 2020.
2. ↑ Data sheet 2,5-dimethyl-4-hydroxy- (2H) -furan-3-one (PDF) from Merck , accessed on March 31, 2012.
3. ↑ ^{a b c d e f} data sheet 4-hydroxy-2,5-dimethyl-3 (2H) -furanone, natural, ≥ 98%, fg from Sigma-Aldrich , accessed on March 31, 2012 ( PDF ).
4. ↑ ^{a b} Entry on strawberry furanone at thegoodscentscompany.com, accessed on December 11, 2017.
5. ^ D. Ulrich, Edelgard Hoberg, Adolf Rapp, Steffen Kecke: Analysis of strawberry flavor - discrimination of aroma types by quantification of volatile compounds. In: Journal of Food Research and Research A. 205, 1997, p. 218, doi: 10.1007 / s002170050154 .
6. ^ Y. Tokitomo, M. Steinhaus, A. Büttner, P. Schieberle: Odor-active constituents in fresh pineapple (Ananas comosus [L.] Merr.) By quantitative and sensory evaluation . In: Bioscience, Biotechnology, and Biochemistry . Vol. 69, No. 7 , 2005, p. 1323-30 , doi : 10.1271 / bbb.69.1323 , PMID 16041138 (English).
7. ↑ D. Janes, D. Kantar, S. Kreft, H. Prosen: Identification of buckwheat (Fagopyrum esculentum Moench) aroma compounds with GC-MS . In: Food Chemistry . Vol. 112, 2008, pp. 120 , doi : 10.1016 / j.foodchem.2008.05.048 (English).
8. ↑ RG Buttery, GR Takeoka, M. Naim, H. Rabinowitch, Y. Nam: Analysis of Furaneol in tomato using dynamic headspace sampling with sodium sulfate. In: Journal of agricultural and food chemistry. Volume 49, Number 9, September 2001, pp. 4349-4351. PMID 11559136 .
9. ^ Roy Teranishi: Flavor chemistry: thirty years of progress . Springer, 1999, ISBN 0-306-46199-4 , pp. 361 ( limited preview in Google Book search).
10. ↑ Mark A. Briggs, Alan H. Haines, Haydn F. Jones: Synthesis of 4-hydroxy-2,5-dimethylfuran-3 (2H) -one (furaneol) from (2R, 3R) -tartaric acid . In: J. Chem. Soc., Perkin Trans. Volume 1 , 1985, pp. 795-798 , doi : 10.1039 / P19850000795 .
11. ↑ ^{a b c d} Edgar Pundsack: Technical aspects of the natural preparation and processing of 4-hydroxy-2,5-dimethyl- (2H) -furan-3-one (furaneol) . Hannover 1999, DNB  960294384/34 (dissertation).
12. ↑ Uwe-Jens Salzer: Handbook of Aromas and Spices . tape 1 . Behrs, 1999, ISBN 3-86022-558-8 , pp. 22 ( limited preview in Google Book search).
13. ^ John C. Leffingwell: Chirality & Odor Perception - The Furaneols .