L-Erythrulose supplier | CasNO.533-50-6

Name
L-(+)-Erythrulose
EINECS
CAS No. 533-50-6
Article Data51
CAS DataBase
Density 1.42g/cm³
Solubility
Melting Point
Formula C₄H₈O₄
Boiling Point 349.6 °C at 760 mmHg
Molecular Weight 120.105
Flash Point 179.4 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2-Butanone,1,3,4-trihydroxy-, (S)-;L-glycero-Tetrulose (7CI,8CI);L-Erythrulose;
PSA 77.76000
LogP -2.09900

Synthetic route

: 2319-57-5
threitol

: 533-50-6
L-erythrulose

Conditions

Conditions	Yield
With [(neocuproine)Pd(OAc)]2(OTf)2; oxygen In water; acetonitrile at 25℃; for 20h; chemoselective reaction;	86%

: 50-00-0
formaldehyd

: 96-26-4
dihydroxyacetone

: 533-50-6
L-erythrulose

Conditions

Conditions	Yield
With D-fructose-6-phosphate aldolase of Escherichia coli Ala129Ser mutant In water at 25℃; for 21h; pH=7.5;	68%
With D-fructose-6-phosphate aldolase of Escherichia coli Ala129Ser mutant at 25℃; pH=7.5; Kinetics; trisethanolamine buffer;

: 312-84-5
D-Serine

: 141-46-8
Glycolaldehyde

: 533-50-6
L-erythrulose

Conditions

Conditions	Yield
With magnesium(II) chloride hexahydrate; flavin adenine dinucleotide (FAD)-containing flavoenzyme from the yeast Rhodotorula gracilis; thiamine pyrophosphate; oxygen In water at 25℃; for 8h; pH=7; Enzymatic reaction;	67%
With transketolase from geobacillus stearothermophilus; D-amino acid oxidase from Rhodotorula gracilis; thiamine diphosphate; magnesium chloride In water at 25℃; for 8h; pH=7; Enzymatic reaction;	44%

: 1113-60-6
3-hydroxy-2-oxopropionic acid

: 141-46-8
Glycolaldehyde

: 533-50-6
L-erythrulose

Conditions

Conditions	Yield
With thiamine pyrophosphate; magnesium chloride; transketolase from spinach 0.1 M glycylglycine buffer, pH 7.5;	60%
With sodium hydroxide; thiamine diphosphate; Lithium hydroxypyruvate; magnesium chloride In water 3-5 d, transketolase (EC 2.2.1.1) from yeast;	60%
at 37℃; transketolase, thiamine pyrophosphate, MgCl2, glycylglycine buffer pH 7.6; other aldehydes;
With thiamine pyrophosphate; magnesium chloride; transketolase from spinach In water glycyl-glycine buffer 0,05 M (pH 7.5);
at 37℃; transketolase, thiamine pyrophosphate, MgCl2, glycylglycine buffer pH 7.6;

: 141-46-8
Glycolaldehyde

: 3369-79-7
Lithium hydroxypyruvate

: 533-50-6
L-erythrulose

Conditions

Conditions	Yield
With sodium hydroxide; magnesium(II) chloride hexahydrate; thiamine diphosphate In water at 25℃; for 24h; pH=7; Enzymatic reaction; optical yield given as %ee; stereoselective reaction;	60%
With thiamine diphosphate; sodium hydroxide; magnesium chloride In glycylglycine buffer at 25℃; for 0.5h; pH=7.5; Enzymatic reaction;	56%
With magnesium(II) chloride hexahydrate; trans ketolase from Geobacillus stearothermophilus; thiamine diphosphate; sodium hydroxide In water at 50℃; for 0.333333h; pH=7.5; Enzymatic reaction; stereospecific reaction;	44%

: 210230-62-9
L-erythrofuranose

: 533-50-6
L-erythrulose

Conditions

Conditions	Yield
With glucose isomerase (EC 5.3.1.5); magnesium sulfate In water at 60℃; for 8h;	39%

: 909878-64-4
meso-erythritol

: 533-50-6
L-erythrulose

Conditions

Conditions	Yield
durch Bact.gluconicum, Bact.xylinoides, Bact.orleanese, Bact.aceti (Hansen);
durch Acetobacter suboxydans;
durch Acetobacter xylinum (Sorbosebakterien);

: 2319-57-5, 2418-52-2, 6968-16-7, 7493-90-5, 7541-59-5
1,2,3,4-butanetetrol

: 533-50-6
L-erythrulose

Conditions

Conditions	Yield
(microbiological transformation);

: 24940-63-4
D-threo-[2,5]hexodiulosonic acid; calcium salt (2:1)

: 533-50-6
L-erythrulose

Conditions

Conditions	Yield
With calcium hydroxide

: 141-46-8
Glycolaldehyde

: 3369-79-7
Lithium hydroxypyruvate

A: 533-50-6, 35007-64-8, 40031-31-0, 496-55-9
D-erythrulose

B: 533-50-6
L-erythrulose

Conditions

Conditions	Yield
With hydrogenchloride; thiamine pyrophosphate; Tris buffer; magnesium chloride at 25℃; spinach transketolase; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With thiamine diphosphate; magnesium chloride pH=7; aq. buffer; Supercritical conditions; Enzymatic reaction; optical yield given as %ee;

...Expand

: 141-46-8
Glycolaldehyde

: Potassium; 2-carboxy-2-oxo-ethanolate

: 533-50-6
L-erythrulose

Conditions

Conditions	Yield
With sodium hydroxide; thiamine pyrophosphate; magnesium chloride for 24h; E. coli transketolase, bovine serum albumin; Yield given;

2-<(4S,5S)-4,5-bis-hydroxymethyl-2,2-dimethyl-<1,3>dioxolan-4-yloxy>-ethanol: 2-<(4S,5S)-4,5-bis-hydroxymethyl-2,2-dimethyl-<1,3>dioxolan-4-yloxy>-ethanol

: 533-50-6
L-erythrulose

Conditions

Conditions	Yield
With sulfuric acid

(S)-<(S)-4-(2-hydroxy-ethoxy>-2,2-dimethyl-<1,3>dioxolan-4-yl>-ethane-1,2-diol: (S)-<(S)-4-(2-hydroxy-ethoxy>-2,2-dimethyl-<1,3>dioxolan-4-yl>-ethane-1,2-diol

: 533-50-6
L-erythrulose

Conditions

Conditions	Yield
With sulfuric acid

: 909878-64-4
meso-erythritol

A: 64-17-5
ethanol

B: 533-50-6
L-erythrulose

C: 124-38-9
carbon dioxide

D cellulose: cellulose

Conditions

Conditions	Yield
durch Acetobacter xylinum;

...Expand

: 1927-27-1
β-hydroxypyruvate

: 141-46-8
Glycolaldehyde

: 533-50-6
L-erythrulose

Conditions

Conditions	Yield
With thiamine diphosphate In phosphate buffer at 25℃; pH=7.0;

: 909878-64-4
meso-erythritol

A: 533-50-6, 35007-64-8, 40031-31-0, 496-55-9
D-erythrulose

B: 533-50-6
L-erythrulose

Conditions

Conditions	Yield
With C30H42N4O6Pd2(2+)*2CF3O3S(1-); p-benzoquinone In water; acetonitrile at 60℃; for 1.2h; Darkness; Overall yield = 61 %; Overall yield = 140 mg; chemoselective reaction;	A n/a B n/a

: 141-46-8
Glycolaldehyde

: 533-50-6
L-erythrulose

Conditions

Conditions	Yield
With Saccharomyces cerevisiae transketolase; thiamine pyrophosphate; magnesium(II) In aq. phosphate buffer at 25℃; for 24h; pH=7; Equilibrium constant; Enzymatic reaction;

: 533-50-6
L-erythrulose

: dihydroxyacetone phosphate disodium salt

: C7H13O10P(2-)

Conditions

Conditions	Yield
With cobalt(II) chloride hexahydrate; rhamnulose-1-phosphate aldolase from Bacteroides thetaiotaomicron In water at 20℃; for 5h; pH=7.5; Inert atmosphere; stereoselective reaction;	92%

: 533-50-6
L-erythrulose

: 623-33-6
glycine ethyl ester hydrochloride

: 333-20-0
potassium thioacyanate

A: ethyl 2-(6-hydroxy-2-thioxotetrahydro-1H-furo[2,3-d]imidazole-1-yl)acetate

B: ethyl 2-(4,5-bis(hydroxymethyl)-2-thioxo-1H-imidazole-1-yl)acetate

Conditions

Conditions	Yield
With acetic acid In water; acetonitrile at 60℃; for 16h;	A 90% B n/a

...Expand

: 533-50-6
L-erythrulose

: 58479-61-1
tert-butylchlorodiphenylsilane

: C36H44O4Si2

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 15h; Inert atmosphere;	86%

: 533-50-6
L-erythrulose

: 3287-99-8, 39110-74-2
benzylamine hydrochloride

: 333-20-0
potassium thioacyanate

: 1-benzyl-6-hydroxytetrahydro-1H-furo[2,3-d]imidazole-2(5H)-thione

Conditions

Conditions	Yield
With acetic acid In water; acetonitrile at 60℃; for 16h;	85%

...Expand

: 533-50-6
L-erythrulose

: 113-24-6
sodium pyruvate

: C7H12O7*H3N

Conditions

Conditions	Yield
With pyruvate aldolase A3SLS0 for 15h; Enzymatic reaction;	85%

: 533-50-6
L-erythrulose

: 3473-63-0
formamidine acetic acid

: 4(5)-(L-glycerodiitol-1-yl)imidazole

Conditions

Conditions	Yield
With ammonia at 75℃; under 40 Torr; for 15h; bomb;	83%

: 533-50-6
L-erythrulose

: 333-20-0
potassium thioacyanate

: 73728-66-2
(2,4-dichlorophenyl)methanamine hydrochloride

A: (3aS,6R,6aR)-1-(2,4-dichlorobenzyl)-6-hydroxytetrahydro-1H-furo[2,3-d]imidazole-2(5H)-thione

B: (R)-1-(2,4-dichlorobenzyl)-5-(1,2-dihydroxyethyl)-1H-imidazole-2(3H)-thione

Conditions

Conditions	Yield
With acetic acid In water; acetonitrile at 60℃; for 16h;	A 83% B n/a

...Expand

: 533-50-6
L-erythrulose

: 67-64-1
acetone

: 115114-86-8
3,4-O-isopropylidene-L-(S)-erythrulose

Conditions

Conditions	Yield
With sodium sulfate; zinc(II) chloride In 1,4-dioxane; methanol for 15h; Ambient temperature;	81%
With copper(II) sulfate at 28℃; for 12h;
With camphor-10-sulfonic acid for 12h; Ambient temperature;

: 533-50-6
L-erythrulose

: 18162-48-6
tert-butyldimethylsilyl chloride

: 677300-95-7
1,4-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-butan-2-one

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 2h;	70%

: C19(13)CH33(2)H3N4O14SP2

: 533-50-6
L-erythrulose

: C21(13)CH37(2)H3N4O16SP2

Conditions

Conditions	Yield
With 1,4-dihydronicotinamide adenine dinucleotide; thiamine diphosphate; magnesium chloride; alcohol dehydrogenase In various solvent(s) at 25℃; for 10h; pH=7.5;	65%

: 533-50-6
L-erythrulose

: 39637-99-5, 20445-33-4
(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride

: 1191924-79-4
C14H15F3O6

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 12h;	63%

: C20(13)CH35(2)H3N4O14SP2

: 533-50-6
L-erythrulose

: C22(13)CH39(2)H3N4O16SP2

Conditions

Conditions	Yield
With 1,4-dihydronicotinamide adenine dinucleotide; thiamine diphosphate; magnesium chloride; alcohol dehydrogenase In various solvent(s) at 25℃; pH=7.5;	62%

: 533-50-6
L-erythrulose

A: 1361017-70-0
methyl 2-hydroxy-4-methoxybutanoate

B: 19444-84-9
3-hydroxyoxolan-2-one

Conditions

Conditions	Yield
With Sn-MCM-41 In methanol at 89.84℃; under 15001.5 Torr; for 5h; Catalytic behavior; Reagent/catalyst; Inert atmosphere;	A 61% B 7%

: 533-50-6
L-erythrulose

A: 5837-73-0
methyl 2-hydroxybut-3-enoate

B: 1361017-70-0
methyl 2-hydroxy-4-methoxybutanoate

C: 19444-84-9
3-hydroxyoxolan-2-one

Conditions

Conditions	Yield
With Sn-MCM-41 In methanol at 139.84℃; under 15001.5 Torr; for 5h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere;	A 60% B 10% C 8%
With tin In methanol at 159.84℃; under 15001.5 Torr; for 5h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere;	A 50% B 18% C 8%

...Expand

: 533-50-6
L-erythrulose

A: 5837-73-0
methyl 2-hydroxybut-3-enoate

B: 1361017-70-0
methyl 2-hydroxy-4-methoxybutanoate

Conditions

Conditions	Yield
With tin (IV) chloride pentahydrate In methanol at 159.84℃; under 15001.5 Torr; for 5h; Catalytic behavior; Reagent/catalyst; Inert atmosphere;	A 7% B 57%

: 533-50-6
L-erythrulose

: 1361017-70-0
methyl 2-hydroxy-4-methoxybutanoate

Conditions

Conditions	Yield
With Sn-SBA-15 In methanol at 89.84℃; under 15001.5 Torr; for 5h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere;	57%

: 533-50-6
L-erythrulose

: (2S)-2-hydroxy-4-oxobutyl phosphate sodium salt

: 4-deoxy-D-fructose 6-phosphate sodium salt

Conditions

Conditions	Yield
With thiamine pyrophosphate; 1,4-dihydronicotinamide adenine dinucleotide; sodium formate; transketolase In water for 24h; pH=7.5; Enzyme kinetics; Condensation; Enzymatic reaction;	52%
With thiamine pyrophosphate; 1,4-dihydronicotinamide adenine dinucleotide; sodium formate; formate dehydrogenase; transketolase In water for 24h; pH=7.5; Condensation; Enzymatic reaction;	52%

: 533-50-6
L-erythrulose

: 20445-33-4, 39637-99-5
(R)-methoxytrifluoromethylphenylacetyl chloride

: 1191924-83-0
C14H15F3O6

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 12h;	51%

: 533-50-6
L-erythrulose

: 77-76-9
2,2-dimethoxy-propane

: 67-64-1
acetone

: 115114-86-8
3,4-O-isopropylidene-L-(S)-erythrulose

Conditions

Conditions	Yield
With toluene-4-sulfonic acid for 0.5h; Ambient temperature;	50%

...Expand

: 533-50-6
L-erythrulose

: di-tert-butyl 2,2’-({[1R-(1α,2α,3α,4α,5α,6α)]-5-amino-2,4,6-tris[benzyloxy]cyclo-hexane-1,3-diyl}diimino)diacetate

: di-tert-butyl 2,2’-({[1R-(1α,2α,3α,4α,5α,6α)]-2,4,6-tris(benzyloxy)-5-[(1,3,4-trihydroxy-butan-2-yl)amino]cyclohexane-1,3-diyl}diimino)diacetate

Conditions

Conditions	Yield
With 5-ethyl-2-methylpyridine borane complex; acetic acid In methanol; toluene at 20℃; for 96h;	31%

: 930-30-3
cyclopent-2-enone

: 533-50-6
L-erythrulose

A: 3-hydroxymethyl-tetrahydro-1,4-dioxa-cyclopenta[cd]pentalene-2a,4a-diol

B: 1,4-dihydroxy-3-hydroxymethyl-2,6-dioxatricyclo[5.2.1.04,10]decane

Conditions

Conditions	Yield
With sodium hydroxide In water at 0℃; for 18h;	A 8% B 30%

...Expand

: 72-18-4
L-valine

: 533-50-6
L-erythrulose

: 119072-55-8, 7188-38-7
tert-butylisonitrile

A: (3R,5S)-N-(tert-butyl)-3-((R)-1,2-dihydroxyethyl)-5-isopropyl-6-oxomorpholine-3-carboxamide

B: (2R,3R,5S)-N-(tert-butyl)-2,3-bis(hydroxymethyl)-5-isopropyl-6-oxomorpholine-3-carboxamide

C: (3S,5R,6R)-N-(tert-butyl)-6-hydroxy-5-(hydroxymethyl)-3-isopropyl-2-oxo-1,4-oxazepane-5-carboxamide

Conditions

Conditions	Yield
With trifluoroethanol; 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 60℃; for 16h; Overall yield = 62 %; Overall yield = 130.6 mg; stereoselective reaction;	A 30% B 21% C 11%

...Expand

: 14694-95-2
Wilkinson's catalyst

: 533-50-6
L-erythrulose

A: 64-17-5
ethanol

B: 909878-64-4
meso-erythritol

: 6968-16-7
rac-threitol

: 95-43-2, 95-44-3, 533-49-3, 583-50-6, 1758-51-6, 7558-94-3, 29825-68-1, 29884-64-8, 38982-45-5
DL-glycero-tetrulose

E: 56-81-5
glycerol

Conditions

Conditions	Yield
In N,N-dimethyl acetamide argon-filled glovebox, durene, bibenzyl, heating 23h, further products; detn. of products by GC;	A 10% B 1-2 C 1-2 D 1-2 E 24%

...Expand

: 640-68-6
D-Val-OH

: 533-50-6
L-erythrulose

: 119072-55-8, 7188-38-7
tert-butylisonitrile

A: (3S,5R)-N-(tert-butyl)-3-((R)-1,2-dihydroxyethyl)-5-isopropyl-6-oxomorpholine-3-carboxamide

B: (3R,5R)-N-(tert-butyl)-3-((R)-1,2-dihydroxyethyl)-5-isopropyl-6-oxomorpholine-3-carboxamide

Conditions

Conditions	Yield
With trifluoroethanol; 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 60℃; for 16h; Overall yield = 38 %; stereoselective reaction;	A 24% B 14%

...Expand

L-Erythrulose Specification

The L-Erythrulose, with CAS registry number 533-50-6, has the systematic name of (3S)-1,3,4-trihydroxybutan-2-one. Besides this, it is also called L-(+)-erythrulose hydrate. And the chemical formula of this chemical is C₄H₈O₄and molecular weight is 120.10392.Its density is 1.420 g/m³.The butyl ketone sugar is erythrose ketone sugar form.

Physical properties of L-Erythrulose: (1)ACD/LogP: -0.98; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 4; (4)#H bond donors: 3; (5)#Freely Rotating Bonds: 6; (6)Polar Surface Area: 44.76 Å²; (7)Index of Refraction: 1.507; (8)Molar Refractivity: 25.17 cm³; (9)Molar Volume: 84.5 cm³; (10)Polarizability: 9.97×10^-24cm³; (11)Surface Tension: 69.1 dyne/cm; (12)Density: 1.42 g/cm³; (13)Flash Point: 179.4 °C; (14)Enthalpy of Vaporization: 68.8 kJ/mol; (15)Boiling Point: 349.6 °C at 760 mmHg; (16)Vapour Pressure: 2.8E-06 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(CO)[C@@H](O)CO
(2)InChI: InChI=1/C4H8O4/c5-1-3(7)4(8)2-6/h3,5-7H,1-2H2/t3-/m0/s1
(3)InChIKey: UQPHVQVXLPRNCX-VKHMYHEABZ
(4)Std. InChI: InChI=1S/C4H8O4/c5-1-3(7)4(8)2-6/h3,5-7H,1-2H2/t3-/m0/s1
(5)Std. InChIKey: UQPHVQVXLPRNCX-VKHMYHEASA-N

Product Name

L-(+)-Erythrulose

Synthetic route

L-Erythrulose Specification

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