2-Keto-3-deoxygluconate supplier

Name
4,5,6-trihydroxy-2-oxo-hexanoic acid
EINECS
CAS No. 17510-99-5
Article Data12
CAS DataBase
Density 1.582 g/cm³
Solubility
Melting Point
Formula C₆H₁₀O₆
Boiling Point 467.5 °C at 760 mmHg
Molecular Weight 178.142
Flash Point 250.6 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms D-erythro-Hexulosonicacid, 3-deoxy- (6CI,7CI);2-Dehydro-3-deoxy-D-gluconic acid;2-Keto-3-Deoxy-D-gluconic acid;2-Oxo-3-deoxy-D-gluconate;2-keto-3-Deoxy-D-gluconate;2-keto-3-Deoxygluconic acid;3-Deoxy-2-oxo-D-gluconate;3-Deoxy-D-erythro-hex-2-ulosonic acid;
PSA 115.06000
LogP -2.25570

Synthetic route

: 328-42-7
Oxalacetic acid

: 453-17-8
D-Glyceraldehyde

A: 56742-44-0
(4R,5R)-3-deoxy-2-hexulosonic acid

B: 17510-99-5
4,5,6-trihydroxy-2-oxohexanoic acid

Conditions

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

...Expand

: 328-42-7
Oxalacetic acid

: 453-17-8
D-Glyceraldehyde

: 17510-99-5
4,5,6-trihydroxy-2-oxohexanoic acid

Conditions

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

D-erythro-2-anilino-4,5,6-trihydroxy-hex-2c-enoic acid 4-lactone: D-erythro-2-anilino-4,5,6-trihydroxy-hex-2c-enoic acid 4-lactone

: 17510-99-5
4,5,6-trihydroxy-2-oxohexanoic acid

Conditions

Conditions	Yield
With acidic cationen-exchanger; water

: 453-17-8
D-Glyceraldehyde

: 113-24-6
sodium pyruvate

A: 56742-44-0
(4R,5R)-3-deoxy-2-hexulosonic acid

B: 17510-99-5
4,5,6-trihydroxy-2-oxohexanoic acid

Conditions

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

...Expand

: 5736-03-8
(d,l) isopropylidene glyceraldehyde

A: 17510-99-5
4,5,6-trihydroxy-2-oxohexanoic acid

B: (4S,5S)-3-deoxy-2-hexulosonic acid

Conditions

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

: 4134-97-8, 30382-30-0, 50455-94-2, 82399-12-0, 4084-27-9
3-deoxyglucosone

A: 7284-15-3
2-deoxy-D-ribonic acid

B: 17510-99-5
4,5,6-trihydroxy-2-oxohexanoic acid

C: 127-17-3
2-oxo-propionic acid

Conditions

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

...Expand

: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

A: 7284-15-3
2-deoxy-D-ribonic acid

B: 17510-99-5
4,5,6-trihydroxy-2-oxohexanoic acid

Conditions

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

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

: 16667-96-2
1,2,5,6-di-O-isopropylidene-α-D-glucofuranose-3-O-(S-methylxanthate)

A: 7284-15-3
2-deoxy-D-ribonic acid

B: 17510-99-5
4,5,6-trihydroxy-2-oxohexanoic acid

Conditions

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

: 4613-62-1
3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside

A: 7284-15-3
2-deoxy-D-ribonic acid

B: 17510-99-5
4,5,6-trihydroxy-2-oxohexanoic acid

Conditions

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

: 453-17-8
D-Glyceraldehyde

: 127-17-3
2-oxo-propionic acid

A: 56742-44-0
(4R,5R)-3-deoxy-2-hexulosonic acid

B: 17510-99-5
4,5,6-trihydroxy-2-oxohexanoic acid

Conditions

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;

...Expand

: 91547-65-8
4-deoxy-L-erythro-5-hexoseulose uronic acid

: 17510-99-5
4,5,6-trihydroxy-2-oxohexanoic acid

Conditions

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;

: 527-07-1
sodium D-gluconate

: 17510-99-5
4,5,6-trihydroxy-2-oxohexanoic acid

Conditions

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;

: 17510-99-5
4,5,6-trihydroxy-2-oxohexanoic acid

: 1518-64-5
3-deoxy-D-mannonic acid

Conditions

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

: 17510-99-5
4,5,6-trihydroxy-2-oxohexanoic acid

: 6338-41-6
5-hydroxymethyl-furan-2-carboxylic acid

Conditions

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;

: 17510-99-5
4,5,6-trihydroxy-2-oxohexanoic acid

A: 1518-64-5
3-deoxy-D-mannonic acid

B: 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
3-deoxy-D-arabino-hexono-1,4-lactone

Conditions

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;

: 17510-99-5
4,5,6-trihydroxy-2-oxohexanoic acid

: 533-67-5
2-Deoxy-D-ribose

Conditions

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

: 110-91-8
morpholine

: 17510-99-5
4,5,6-trihydroxy-2-oxohexanoic acid

: 1-N-morpholino-3,4,5-trihydroxypentene-1

Conditions

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

: 17510-99-5
4,5,6-trihydroxy-2-oxohexanoic acid

: 2817-48-3, 79580-64-6, 96154-36-8
3-deoxy-D-arabino-hexonic acid calcium salt

Conditions

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

: 17510-99-5
4,5,6-trihydroxy-2-oxohexanoic acid

: 27244-54-8
3-deoxy-D-erythro-hex-2-ulosonic acid 6-phosphate

Conditions

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

: 17510-99-5
4,5,6-trihydroxy-2-oxohexanoic acid

: 3238-40-2
furan-2,5-dicarboxylic acid

Conditions

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

: 64-17-5
ethanol

: 17510-99-5
4,5,6-trihydroxy-2-oxohexanoic acid

A: 6338-41-6
5-hydroxymethyl-furan-2-carboxylic acid

B: 76448-73-2
ethyl 5-(hydroxymethyl)furan-2-carboxylate

Conditions

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

...Expand

: 17510-99-5
4,5,6-trihydroxy-2-oxohexanoic acid

: 7284-15-3
2-deoxy-D-ribonic acid

Conditions

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

2-Keto-3-deoxygluconate Specification

The 2-Keto-3-deoxygluconate, with the CAS registry number 17510-99-5, is also known as 3-Deoxy-2-oxo-D-gluconate. This chemical's molecular formula is C₆H₁₀O₆ and molecular weight is 178.14. Its IUPAC name is called 3-deoxy-D-erythro-hex-2-ulosonic acid.

Physical properties of 2-Keto-3-deoxygluconate: (1)ACD/LogP: -2.82; (2)ACD/LogD (pH 5.5): -5.85; (3)ACD/LogD (pH 7.4): -6.55; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 6; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 8; (11)Index of Refraction: 1.551; (12)Molar Refractivity: 35.96 cm³; (13)Molar Volume: 112.5 cm³; (14)Surface Tension: 85.8 dyne/cm; (15)Density: 1.582 g/cm³; (16)Flash Point: 250.6 °C; (17)Enthalpy of Vaporization: 84.11 kJ/mol; (18)Boiling Point: 467.5 °C at 760 mmHg; (19)Vapour Pressure: 1.05E-10 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(C(=O)O)C[C@H](O)[C@H](O)CO
(2)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
(3)InChIKey: WPAMZTWLKIDIOP-WVZVXSGGBW

Product Name

4,5,6-trihydroxy-2-oxo-hexanoic acid

Synthetic route

2-Keto-3-deoxygluconate Specification

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