1684-29-3

Basic information

• Product Name: 5-ketofructose
• Synonyms: 5-ketofructose;Nsc 231823;5-dehydro-D-fructose
• CAS NO: 1684-29-3
• Molecular Formula: C₆H₁₀O₆
• Molecular Weight: 178.14
• Mol File: 1684-29-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: 175-176 °C
• Boiling Point: 516.9°Cat760mmHg
• Flash Point: 280.5°C
• Appearance: /
• Density: 1.582g/cm³
• Vapor Pressure: 7.63E-13mmHg at 25°C
• Refractive Index: 1.551
• PKA: 11.11±0.20(Predicted)
• CAS DataBase Reference: 5-ketofructose(CAS DataBase Reference)
• NIST Chemistry Reference: 5-ketofructose(1684-29-3)
• EPA Substance Registry System: 5-ketofructose(1684-29-3)

Safety Data

• Hazardous Substances Data: 1684-29-3(Hazardous Substances Data)

Usage

Definition

ChEBI: A hexose obtained by selective dehydration at the 5-position of D-fructose.

InChI:InChI=1/C6H10O6/c7-1-3(9)5(11)6(12)4(10)2-8/h5-8,11-12H,1-2H2

Synthetic route

D-Fructose (57-48-7) → D-5-ketofructose (1684-29-3)

Conditions	Yield
mit Hilfe von Acetobacter suboxydans;
mit Hilfe von Gluconobacter cerinus;
With fructose dehydrogenase In aq. buffer pH=6; Kinetics; Reagent/catalyst; Electrochemical reaction; Enzymatic reaction;

fructopyranose (6347-01-9) → D-5-ketofructose (1684-29-3)

Conditions	Yield
With culture of Gluconobactor cerinus (ATCC catalogue number IFO 3267)

D-5-ketofructose (1684-29-3) → D-threo-2,5-hexodiulose 1-phosphate (16808-78-9)

Conditions	Yield
With potassium hydroxide; triethanolamine; magnesium acetate; phosphoenolpyruvate potassium salt; ATP; hexokinase In water for 7h;	72%

D-5-ketofructose (1684-29-3) → D-threo-2,5-hexodiulose 1,6-biphosphate (39217-32-8)

Conditions	Yield
With potassium hydroxide; pyruvate kinase; phosphofructo kinase; magnesium acetate; triethanolamine hydrochloride; phosphoenolpyruvate potassium salt; ATP; hexokinase In water	60%

D-5-ketofructose (1684-29-3) + 9H-fluoren-9-amine hydrochloride (5978-75-6) → N-(9-Fluorenyl)-2,5-anhydro-2,5-imino-D-glucitol

Conditions	Yield
With sodium cyanoborohydride In methanol for 24h; Heating;	33%

D-5-ketofructose (1684-29-3) + Benzhydrylamine (91-00-9) → N-Benzhydryl-2,5-anhydro-2,5-imino-D-mannitol (132198-33-5) + (2S,3R,4R,5R)-1-Benzhydryl-2,5-bis-hydroxymethyl-pyrrolidine-3,4-diol (132198-31-3) + N-Benzhydryl-2,5-anhydro-2,5-imino-L-iditol (132198-32-4)

Conditions	Yield
With sodium cyanoborohydride; acetic acid In methanol for 6h; Heating;	A 4% B 28% C n/a
With sodium cyanoborohydride; acetic acid In methanol for 6h; Heating; Yield given;	A 4% B 28% C n/a
With sodium cyanoborohydride In methanol Heating; Yield given. Yields of byproduct given;
With sodium cyanoborohydride In methanol Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

D-5-ketofructose (1684-29-3) + N,N-diphenylhydrazine hydrochloride (530-47-2) → N-(Diphenylamino)-2,5-anhydro-2,5-imino-D-glucitol

Conditions	Yield
With sodium cyanoborohydride In methanol for 10h; Heating;	10%

D-5-ketofructose (1684-29-3) + 4-fluoroaniline (371-40-4) → N-(4-Fluorophenyl)-2,5-anhydro-2,5-imino-D-mannitol + N-(4-Fluorophenyl)-2,5-anhydro-2,5-imino-D-glucitol + N-(4-Fluorophenyl)-2,5-anhydro-2,5-imino-L-iditol

Conditions	Yield
With sodium cyanoborohydride; acetic acid In methanol Heating;	A 7% B 7% C 2%

D-5-ketofructose (1684-29-3) + 4-nitrophenylhydrazone (100-16-3) → D-threo-[2,5]hexodiulose-bis-(4-nitro-phenylhydrazone) (98924-67-5)

Conditions	Yield
With acetic acid

D-5-ketofructose (1684-29-3) + (S)-1-phenyl-ethylamine (2627-86-3) → N-<(S)-α-Methylbenzyl>-2,5-anhydro-2,5-imino-D-mannitol + N-<(S)-α-Methylbenzyl>-2,5-anhydro-2,5-imino-D-glucitol

Conditions	Yield
With sodium cyanoborohydride; acetic acid In methanol for 3h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

D-5-ketofructose (1684-29-3) + (R)-1-phenyl-ethyl-amine (3886-69-9) → N-<(R)-α-Methylbenzyl>-2,5-anhydro-2,5-imino-D-mannitol + N-<(R)-α-Methylbenzyl>-2,5-anhydro-2,5-imino-D-glucitol + N-<(R)-α-Methylbenzyl>-2,5-anhydro-2,5-imino-L-iditol

Conditions	Yield
With sodium cyanoborohydride; acetic acid In methanol for 6h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

D-5-ketofructose (1684-29-3) + 4-fluoro-2-phenethylamine (1583-88-6) → N-(4-Fluorophenethyl)-2,5-anhydro-2,5-imino-D-mannitol + N-(4-Fluorophenethyl)-2,5-anhydro-2,5-imino-D-glucitol + N-(4-Fluorophenethyl)-2,5-anhydro-2,5-imino-L-iditol

Conditions	Yield
With sodium cyanoborohydride; acetic acid In methanol for 5h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

D-5-ketofructose (1684-29-3) + N-butylamine (109-73-9) → N-Butyl-2,5-anhydro-2,5-imino-D-glucitol

Conditions	Yield
With sodium cyanoborohydride; acetic acid In methanol for 18h; Heating; Yield given;

D-5-ketofructose (1684-29-3) + 1-aminooctadecane (124-30-1) → N-Stearyl-2,5-anhydro-2,5-imino-D-mannitol + N-Stearyl-2,5-anhydro-2,5-imino-D-glucitol + N-Stearyl-2,5-anhydro-2,5-imino-L-iditol

Conditions	Yield
With sodium cyanoborohydride; acetic acid In methanol for 18h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

D-5-ketofructose (1684-29-3) + propan-1-ol-3-amine (156-87-6) → N-(3-Hydroxypropyl)-2,5-anhydro-2,5-imino-D-mannitol + N-(3-Hydroxypropyl)-2,5-anhydro-2,5-imino-D-glucitol + N-(3-Hydroxypropyl)-2,5-anhydro-2,5-imino-L-iditol

Conditions	Yield
With sodium cyanoborohydride; acetic acid In methanol for 3h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

D-5-ketofructose (1684-29-3) + Benzhydrylamine (91-00-9) → (2S,3R,4R,5R)-1-Benzhydryl-2,5-bis-hydroxymethyl-pyrrolidine-3,4-diol (132198-31-3)

Conditions	Yield
With sodium tetrahydroborate

D-5-ketofructose (1684-29-3) → mannitol (69-65-8) + D-sorbitol (50-70-4) + L-iditol (488-45-9)

Conditions	Yield
With hydrogen; palladium on activated charcoal at 100℃; under 75006 Torr; Product distribution;

D-5-ketofructose (1684-29-3) → 2,5-anhydro-2,5-imino-D-glucitol (132295-44-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH4 2: H2 / hydrogenation catalyst View Scheme
Multi-step reaction with 2 steps 1: 28 percent / HOAc, NaBH3CN / methanol / 6 h / Heating 2: 91 percent / H2 / 20percent Pd(OH)2/C / methanol / 3102.9 Torr View Scheme
Multi-step reaction with 2 steps 1: NaCNBH3 / methanol / Heating 2: 91 percent / H2 / 20 percent Pd(OH)2/C View Scheme

D-5-ketofructose (1684-29-3) → (2S,3R,4R,5R)-1-(3-Amino-benzyl)-2,5-bis-hydroxymethyl-pyrrolidine-3,4-diol

Conditions	Yield
Multi-step reaction with 4 steps 1: NaBH4 2: H2 / hydrogenation catalyst 4: H2 / Lindlar catalyst View Scheme

D-5-ketofructose (1684-29-3) → (2S,3R,4R,5R)-2,5-Bis-hydroxymethyl-1-(3-nitro-benzyl)-pyrrolidine-3,4-diol (198076-36-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: NaBH4 2: H2 / hydrogenation catalyst View Scheme

D-5-ketofructose (1684-29-3) → 2,5-dideoxy-2,5-imino-D-mannitol (59920-31-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 4 percent / HOAc, NaBH3CN / methanol / 6 h / Heating 2: 50 percent / H2 / 20percent Pd(OH)2/C / methanol / 2585.7 Torr View Scheme

Upstream product

• 57-48-7 D-Fructose 
• 6347-01-9 fructopyranose 

Downstream Products

• 98924-67-5 D-threo-[2,5]hexodiulose-bis-(4-nitro-phenylhydrazone) 
• 16808-78-9 D-threo-2,5-hexodiulose 1-phosphate 
• 39217-32-8 D-threo-2,5-hexodiulose 1,6-biphosphate 
• 132198-33-5 N-Benzhydryl-2,5-anhydro-2,5-imino-D-mannitol 
• 132198-31-3 (2S,3R,4R,5R)-1-Benzhydryl-2,5-bis-hydroxymethyl-pyrrolidine-3,4-diol 
• 132198-32-4 N-Benzhydryl-2,5-anhydro-2,5-imino-L-iditol 
• 69-65-8 mannitol 
• 50-70-4 D-sorbitol 
• 488-45-9 L-iditol 
• 132295-44-4 2,5-anhydro-2,5-imino-D-glucitol 
• 198076-36-7 (2S,3R,4R,5R)-2,5-Bis-hydroxymethyl-1-(3-nitro-benzyl)-pyrrolidine-3,4-diol 

Related news

Production of the potential sweetener 5-ketofructose (cas 1684-29-3) from fructose in fed-batch cultivation with Gluconobacter oxydans09/24/2019

Sweeteners improve the dietary properties of many foods. A candidate for a new natural sweetener is 5-ketofructose. In this study a fed-batch process for the production of 5-ketofructose was developed. A Gluconobacter oxydans strain overexpressing a fructose dehydrogenase from G. japonicus was u...detailed

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