17510-99-5

Basic information

• Product Name: 4,5,6-trihydroxy-2-oxo-hexanoic acid
• Synonyms: 2-Keto-3-deoxy-D-gluconic acid;4,5,6-trihydroxy-2-oxo-hexanoic acid;2-keto-3-deoxygluconate;2-Keto-3-deoxy-D-gluconic acid lithium salt;3-Deoxy-D-erythro-2-hexulosonic acid lithium salt;KDG;Lithium 2-keto-3-deoxy-D-gluconate;2-dehydro-3-deoxy-D-gluconic acid
• CAS NO: 17510-99-5
• Molecular Formula: C₆H₁₀O₆
• Molecular Weight: 178.14
• Mol File: 17510-99-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 467.5 °C at 760 mmHg
• Flash Point: 250.6 °C
• Appearance: /
• Density: 1.582 g/cm³
• Vapor Pressure: 1.05E-10mmHg at 25°C
• Refractive Index: 1.551
• Storage Temp.: ?20°C
• CAS DataBase Reference: 4,5,6-trihydroxy-2-oxo-hexanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5,6-trihydroxy-2-oxo-hexanoic acid(17510-99-5)
• EPA Substance Registry System: 4,5,6-trihydroxy-2-oxo-hexanoic acid(17510-99-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 17510-99-5(Hazardous Substances Data)

Usage

Definition

ChEBI: The 2-dehydro-3-deoxy derivative of D-gluconic acid.

InChI:InChI=1/C6H10O6/c7-2-5(10)3(8)1-4(9)6(11)12/h3,5,7-8,10H,1-2H2,(H,11,12)/t3-,5+/m0/s1

Synthetic route

Oxalacetic acid (328-42-7) + D-Glyceraldehyde (453-17-8) → (4R,5R)-3-deoxy-2-hexulosonic acid (56742-44-0) + 4,5,6-trihydroxy-2-oxohexanoic acid (17510-99-5)

Conditions	Yield
(i) aq. KOH, (ii) (decarboxylation); Multistep reaction;

Oxalacetic acid (328-42-7) + D-Glyceraldehyde (453-17-8) → 4,5,6-trihydroxy-2-oxohexanoic acid (17510-99-5)

Conditions	Yield
(i) aq. KOH, (ii) (decarboxylation); Multistep reaction;

D-erythro-2-anilino-4,5,6-trihydroxy-hex-2c-enoic acid 4-lactone → 4,5,6-trihydroxy-2-oxohexanoic acid (17510-99-5)

Conditions	Yield
With acidic cationen-exchanger; water

D-Glyceraldehyde (453-17-8) + sodium pyruvate (113-24-6) → (4R,5R)-3-deoxy-2-hexulosonic acid (56742-44-0) + 4,5,6-trihydroxy-2-oxohexanoic acid (17510-99-5)

Conditions	Yield
With Sulfolobus solfataricus 2-keto-3-deoxygluconate aldolase; sodium phosphate at 70℃; pH=6; Enzyme kinetics;

(d,l) isopropylidene glyceraldehyde (5736-03-8) → 4,5,6-trihydroxy-2-oxohexanoic acid (17510-99-5) + (4S,5S)-3-deoxy-2-hexulosonic acid

Conditions	Yield
With Sulfolobus solfataricus 2-keto-3-deoxygluconate aldolase at 50℃; for 3h; pH=7; Title compound not separated from byproducts;

3-deoxyglucosone (4134-97-8, 30382-30-0, 50455-94-2, 82399-12-0, 4084-27-9) → 2-deoxy-D-ribonic acid (7284-15-3) + 4,5,6-trihydroxy-2-oxohexanoic acid (17510-99-5) + 2-oxo-propionic acid (127-17-3)

Conditions	Yield
With oxygen; sodium hydroxide In water at 130℃; for 5h; pH=8; Kinetics; Sealed tube;

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 2-deoxy-D-ribonic acid (7284-15-3) + 4,5,6-trihydroxy-2-oxohexanoic acid (17510-99-5)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: 1H-imidazole; sodium hydride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 1.3: 1 h / Inert atmosphere 2.1: tri-n-butyl-tin hydride / toluene / Reflux 3.1: sulfuric acid / water / 1 h / Reflux 4.1: sodium hydroxide; oxygen; catalase / water / 5 h / 25 °C / pH 7.0 / Enzymatic reaction 5.1: sodium hydroxide; oxygen / water / 5 h / 130 °C / pH 8 / Sealed tube View Scheme

1,2,5,6-di-O-isopropylidene-α-D-glucofuranose-3-O-(S-methylxanthate) (16667-96-2) → 2-deoxy-D-ribonic acid (7284-15-3) + 4,5,6-trihydroxy-2-oxohexanoic acid (17510-99-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: tri-n-butyl-tin hydride / toluene / Reflux 2: sulfuric acid / water / 1 h / Reflux 3: sodium hydroxide; oxygen; catalase / water / 5 h / 25 °C / pH 7.0 / Enzymatic reaction 4: sodium hydroxide; oxygen / water / 5 h / 130 °C / pH 8 / Sealed tube View Scheme

3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside (4613-62-1) → 2-deoxy-D-ribonic acid (7284-15-3) + 4,5,6-trihydroxy-2-oxohexanoic acid (17510-99-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid / water / 1 h / Reflux 2: sodium hydroxide; oxygen; catalase / water / 5 h / 25 °C / pH 7.0 / Enzymatic reaction 3: sodium hydroxide; oxygen / water / 5 h / 130 °C / pH 8 / Sealed tube View Scheme

D-Glyceraldehyde (453-17-8) + 2-oxo-propionic acid (127-17-3) → (4R,5R)-3-deoxy-2-hexulosonic acid (56742-44-0) + 4,5,6-trihydroxy-2-oxohexanoic acid (17510-99-5)

Conditions	Yield
With 2-keto-3-deoxygluconate aldolase from Sulfolobus acidocaldarius at 50℃; Reagent/catalyst; Aldol Addition; Enzymatic reaction; stereoselective reaction;	A n/a B n/a
With recombinant aldolase A0A081HJP9 from Pseudomonas aeruginosa In aq. buffer for 24h; pH=8; Reagent/catalyst; Aldol Addition; Enzymatic reaction;

4-deoxy-L-erythro-5-hexoseulose uronic acid (91547-65-8) → 4,5,6-trihydroxy-2-oxohexanoic acid (17510-99-5)

Conditions	Yield
With Saccharophagus degradans 2-40T 4-deoxy-L-erythro-5-hexoseulose uronate reductase; NADH In aq. buffer at 30℃; for 0.666667h; pH=7; Reagent/catalyst; Enzymatic reaction;

sodium D-gluconate (527-07-1) → 4,5,6-trihydroxy-2-oxohexanoic acid (17510-99-5)

Conditions	Yield
With gluconate dehydratase In aq. phosphate buffer at 35℃; for 8h; pH=7.5; Enzymatic reaction;	2.2 g
With dihydroxyacid dehydratase at 60℃; for 24.75h; pH=8.35; Enzymatic reaction;

4,5,6-trihydroxy-2-oxohexanoic acid (17510-99-5) → 3-deoxy-D-mannonic acid (1518-64-5)

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate In water at 0 - 30℃; pH=4.3 - 14; Product distribution / selectivity;	95%

4,5,6-trihydroxy-2-oxohexanoic acid (17510-99-5) → 5-hydroxymethyl-furan-2-carboxylic acid (6338-41-6)

Conditions	Yield
With hydrogen bromide In water; acetic acid at 120℃; under 1551.49 Torr; for 0.666667h; Temperature; Reagent/catalyst; Solvent; Flow reactor;	70%
With trifluoroacetic acid at 60℃; for 4h; Reagent/catalyst;

4,5,6-trihydroxy-2-oxohexanoic acid (17510-99-5) → 3-deoxy-D-mannonic acid (1518-64-5) + 3-deoxy-D-arabino-hexono-1,4-lactone (499-87-6, 6936-66-9, 20261-95-4, 20261-96-5, 50480-80-3, 55658-88-3, 66537-22-2, 79645-44-6, 104760-51-2, 119008-23-0, 134524-29-1)

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In water at 48℃; for 9 - 20h; Product distribution / selectivity;	A 26% B 54%
With sulfuric acid; hydrogen; palladium 10% on activated carbon In water at 48℃; for 9 - 20h; Product distribution / selectivity;

4,5,6-trihydroxy-2-oxohexanoic acid (17510-99-5) → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With cerium(IV) sulphate; sulfuric acid; palladium 10% on activated carbon In water at 37℃;	51%

morpholine (110-91-8) + 4,5,6-trihydroxy-2-oxohexanoic acid (17510-99-5) → 1-N-morpholino-3,4,5-trihydroxypentene-1

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 3h; Heating / reflux;	40%

4,5,6-trihydroxy-2-oxohexanoic acid (17510-99-5) → 3-deoxy-D-arabino-hexonic acid calcium salt (2817-48-3, 79580-64-6, 96154-36-8)

Conditions	Yield
Stage #1: 4,5,6-trihydroxy-2-oxohexanoic acid With hydrogen; palladium 10% on activated carbon In water at 48℃; Stage #2: With calcium hydroxide In water for 1h; Stage #3: With carbon dioxide

4,5,6-trihydroxy-2-oxohexanoic acid (17510-99-5) → 3-deoxy-D-erythro-hex-2-ulosonic acid 6-phosphate (27244-54-8)

Conditions	Yield
With Saccharophagus degradans 2-40T 2-keto-3-deoxy-D-gluconate kinase; ATP In aq. buffer at 30℃; for 1h; Enzymatic reaction;

4,5,6-trihydroxy-2-oxohexanoic acid (17510-99-5) → furan-2,5-dicarboxylic acid (3238-40-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen bromide / water; acetic acid / 0.67 h / 120 °C / 1551.49 Torr / Flow reactor 2: Ru/Pt on active carbon; oxygen / water / 20 h / 90 °C / 1034.32 Torr / Alkaline conditions View Scheme
Multi-step reaction with 2 steps 1: trifluoroacetic acid / 4 h / 60 °C 2: acetic acid; cobalt(II) acetate; sodium bromide; manganese(II) acetate; oxygen / 1 h / 180 °C / 42133 Torr View Scheme

ethanol (64-17-5) + 4,5,6-trihydroxy-2-oxohexanoic acid (17510-99-5) → 5-hydroxymethyl-furan-2-carboxylic acid (6338-41-6) + ethyl 5-(hydroxymethyl)furan-2-carboxylate (76448-73-2)

Conditions	Yield
With sulfuric acid In water at 80℃; for 18h; Temperature; Overall yield = ~ 70 %;

4,5,6-trihydroxy-2-oxohexanoic acid (17510-99-5) → 2-deoxy-D-ribonic acid (7284-15-3)

Conditions	Yield
With water; dihydrogen peroxide at 20℃; for 12h;

Upstream product

• 453-17-8 D-Glyceraldehyde 
• 113-24-6 sodium pyruvate 
• 56-82-6 Glyceraldehyde 
• 527-07-1 sodium D-gluconate 
• 91547-65-8 4-deoxy-L-erythro-5-hexoseulose uronic acid 
• 127-17-3 2-oxo-propionic acid 
• 4613-62-1 3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 
• 16667-96-2 1,2,5,6-di-O-isopropylidene-α-D-glucofuranose-3-O-(S-methylxanthate) 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 4134-97-8 3-deoxyglucosone 
• 5736-03-8 (d,l) isopropylidene glyceraldehyde 
• 328-42-7 Oxalacetic acid 

Downstream Products

• 6338-41-6 5-hydroxymethyl-furan-2-carboxylic acid 
• 3238-40-2 furan-2,5-dicarboxylic acid 
• 76448-73-2 ethyl 5-(hydroxymethyl)furan-2-carboxylate 
• 7284-15-3 2-deoxy-D-ribonic acid 
• 2817-48-3 calcium 3-deoxy-D-arabino-hexonate 
• 1518-64-5 3-deoxy-D-mannonic acid 
• 499-87-6 3-deoxy-D-arabino-hexono-1,4-lactone 
• 533-67-5 2-Deoxy-D-ribose 

Relevant articles and documents

-

-

SYNTHESIS OF FDCA AND FDCA PRECURSORS FROM GLUCONIC ACID DERIVATIVES

The present invention provides methods of method of synthesizing 2,5-furan dicarboxylic acid (FDCA) and FDCA precursor molecules. The methods involve performing a chemical dehydration reaction on a gluconic acid derivative in the presence of a dehydration catalyst. In some embodiments the gluconic acid derivative can be 2-dehydro-3-deoxy gluconic acid (DHG) or an ester thereof, 2-ketogluconic acid (2KGA) or an ester thereof, and 5-ketogluconic acid (5KGA) or an ester thereof. The 2,5-furan dicarboxylic acid precursor molecule is thereby synthesized, which can be converted into FDCA. The chemical dehydration can be performed by a variety of acid basic catalysts.

Validation of the metabolic pathway of the alginate-derived monomer in Saccharophagus degradans 2-40T by gas chromatography–mass spectrometry

Marine macroalgae are potential resources for the sustainable production of biofuels and bio-based chemicals. Alginate, a major component of brown macroalgae, consists of two uronate monomers, which are further non-enzymatically converted to 4-deoxy-L-erythro-5-hexoseulose uronate (DEH). In several marine bacteria, DEH is known to be metabolized via three enzymatic steps, consisting of DEH reductase, 2-keto-3-deoxy-D-gluconate (KDG) kinase, and 2-keto-3-deoxy-phosphogluconate (KDPG) aldolase, which yields two glycolytic intermediates: D-glyceraldehyde-3-phosphate and pyruvate. However, such functions of these enzymes for the DEH pathway have rarely been experimentally validated. In the present study, the DEH metabolic pathway was investigated in Saccharophagus degradans 2-40T, a marine bacterium that utilizes alginate. Through in vitro tests assisted by gas chromatography/mass spectrometry and gas chromatography/time-of-flight mass spectrometry, the purified enzymes were functionally confirmed and annotated as dehR, kdgK, and kdpgA, respectively. In conclusion, we report the in vitro validation of the metabolic pathway of DEH monomerized from alginate.