40762-22-9

Basic information

• Product Name: D-GLUCOSE-1-13C
• Synonyms: D-[1-13C]GLUCOSE;D(+)-GLUCOSE-1-(13C);D-GLUCOSE-1-13C;D-GLUCOSE-1-13C, 99 ATOM % 13C;dextrose-1-13c;1-D;D-Glucose-1-13C min. Chem. 99% min. Isot. 99%;2-D, 98%)
• CAS NO: 40762-22-9
• Molecular Formula: C₆H₁₂O₆
• Molecular Weight: 181.16
• Product Categories: 13C & 2H Sugars;Carbohydrate Synthesis;Monosaccharides;Specialty Synthesis;carbohydrate
• Mol File: 40762-22-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 150-152 °C(lit.)
• Appearance: /
• Storage Temp.: Room Temperature
• Solubility: Methanol (Slightly, Heated), Water
• BRN: 2263682
• CAS DataBase Reference: D-GLUCOSE-1-13C(CAS DataBase Reference)
• NIST Chemistry Reference: D-GLUCOSE-1-13C(40762-22-9)
• EPA Substance Registry System: D-GLUCOSE-1-13C(40762-22-9)

Safety Data

• WGK Germany: 3
• F: 3
• Hazardous Substances Data: 40762-22-9(Hazardous Substances Data)

Usage

Chemical Properties

D-GLUCOSE-1-13C is White powder

Uses

Different sources of media describe the Uses of 40762-22-9 differently. You can refer to the following data:
1. D-GLUCOSE-1-13C is a simple sugar that is present in plants. A monosaccharide that may exist in open chain or cyclic conformation if in solution. It plays a vital role in photosynthesis and fuels the energy required for cellular respiration. D-Glucose is used in various metabolic processes including enzymic synthesis of cyclohexyl-α and β-D-glucosides. D-GLUCOSE-1-13C Can also be used as a diagnostic tool in detection of type 2 diabetes mellitus and potentially Huntington's disease through analysis of blood-glucose in type 1 diabetes mellitus.
2. D-Glucose-1-13C can be used:To predict the primary reaction mechanism in pyrolysis of glucose.To study C?C bond cleavage mechanism in the conversion of labeled glucose into alkanediols using Ni?MgO?ZnO catalyst.In tracer enrichment determination in blood plasma using high-resolution mass spectrometry.

Synthetic route

D-Arabinose (10323-20-3) + potassium [13C]cyanide → [1-13C]D-glucose (40762-22-9) + <1-13C>-D-mannose (70849-31-9)

Conditions	Yield
With hydrogen; Pd-BaSO4 1.) pH 7.2-7.5; Multistep reaction;

<1-13C>-D-mannose (70849-31-9) → [1-13C]D-glucose (40762-22-9) + D-<2-13C>glucose (70849-16-0, 83379-35-5, 83379-36-6, 70849-17-1)

Conditions	Yield
molybdenum(VI) oxide In water at 92℃;

α- and β-D-<1-13C>mannose (40010-55-7, 40010-56-8, 56746-22-6, 60821-16-1, 60821-17-2, 60821-20-7, 60821-21-8) → [1-13C]D-glucose (40762-22-9) + <1-13C>-D-fructose (108311-21-3)

Conditions	Yield
at 25℃; mildly basic condition; equilibrium;

[1-13C]D-glucose (40762-22-9) → C5(13)CH5O9(3-)*3Na(1+) + C5(13)CH5O9(3-)*3Na(1+) + 1-13C-D-glucaric acid sodium salt

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium carbonate In water at 5℃; Electrochemical reaction; optical yield given as %de;	A n/a B n/a C 90%

L-Cysteine (52-90-4) + [1-13C]D-glucose (40762-22-9) → 2(RS)-<2-13C>-D-gluco-(1',2',3',4',5'-pentahydroxypentyl)thiazolidine-4(R)-carboxylic acid (110224-42-5, 110270-22-9)

Conditions	Yield
With pyridine; D-glucose In methanol for 4h; Heating;	75%

[1-13C]D-glucose (40762-22-9) → monopotassium D-[1-13C]-glucarate (1350968-07-8)

Conditions	Yield
Stage #1: [1-13C]D-glucose With nitric acid; sodium nitrite at 20 - 60℃; Stage #2: With potassium hydroxide In water at 0℃; for 1h; pH=10 - 11; Stage #3: With hydrogenchloride In water pH=3.5;	42%

methanol (67-56-1) + [1-13C]D-glucose (40762-22-9) → [C-1]-methyl-α,β-D-glucopyranoside (83944-17-6)

Conditions	Yield
With acetyl chloride at 70℃; Yield given;

[1-13C]D-glucose (40762-22-9) → D-(1-13C)glucitol (132144-93-5, 132202-26-7, 132202-29-0)

Conditions	Yield
With sodium tetrahydroborate In water for 3h; Ambient temperature; pH 10.5 (1M NaOH);

[1-13C]D-glucose (40762-22-9) → (13)C17H26O10

Conditions	Yield
With AP-medium; Rauwolfia serpentina cells at 21℃; for 432h; biosynthesis; Irradiation;

[1-13C]D-glucose (40762-22-9) + Cellobiose (13360-52-6) → <2-13C>acetate (19729-98-7, 56465-68-0) + [2-13C]succinate + α-[1-13C]glucose-6-phosphate + β-[1-13C]glucose-6-phosphate

Conditions	Yield
With Fibrobacter succinogenes 095 In various solvent(s) at 37℃; Kinetics; Further Variations:; Reagents; Hydrolysis; Oxidation; Enzymatic reaction;

[1-13C]D-glucose (40762-22-9) + dextrinsoybean meal → C12(13)C9H23NO4

Conditions	Yield
With dried yeast; calcium carbonate; Streptomyces exfoliatus 2419-SVT2 In water at 27℃; for 15h; pH=6.2; biosynthesis;

[1-13C]D-glucose (40762-22-9) → C5(13)CH6N2O

Conditions	Yield
With Saccharomyces cerevisiae ATTC 7752 (IFO 1234) for 12h; Microbiological reaction;

[1-13C]D-glucose (40762-22-9) → C4(13)C2H6N2O

Conditions	Yield
With Escherichia coli B WG2 (pdxH- auxotroph) for 15h; Microbiological reaction;

L-lysine (56-87-1) + L-arginine (74-79-3) + [1-13C]D-glucose (40762-22-9) → C17(13)CH32N6O6

[1-13C]D-glucose (40762-22-9) + Boc-Lys-OH (13734-28-6) + 1,2-diamino-benzene (95-54-5) → N6-[1-[13]C-2,3-dihydroxy-4-(2-quinoxalinyl)butyl]lysine

Conditions	Yield
With diethylenetriaminopentaacetic acid In phosphate buffer; water at 70℃; for 48h; pH=7.4; Maillard process;

[1-13C]D-glucose (40762-22-9) + Boc-Lys-OH (13734-28-6) + aminoguanidine (79-17-4) → N6-[1-[13C]-4-(3-amino-1,2,4-triazin-5-yl)-2,3-dihydroxybutyl]lysine

Conditions	Yield
Maillard process;

[1-13C]D-glucose (40762-22-9) → C34 botryococcene + C30 botryococcene + tetramethylsqualene

Conditions	Yield
With neomycin B; Botryococcenes brauni race B at 25℃; for 336000h; Microbiological reaction;	A 43.2 mg B 0.5 mg C 0.8 mg

[1-13C]D-glucose (40762-22-9) + Nα-hippuryllysine (740-63-6, 108392-04-7) → [1-13C]Nε-(1-deoxy-D-fructos-1-yl)hippuril-lisine

Conditions	Yield
In methanol for 22h; Heating;	50 mg

[1-13C]D-glucose (40762-22-9) + benzyl bromide (100-39-0) → C1-13C-tri-O-benzyl-D-glucal (444313-77-3)

Conditions	Yield
Multistep reaction.;

[1-13C]D-glucose (40762-22-9) → 2,3,4,6-tetra-O-benzyl-D-(1-13C)glucopyranose

Conditions	Yield
Multi-step reaction with 3 steps 1: acetyl chloride / 70 °C 2: NaH, tetrabutylammonium iodide / dimethylformamide / Ambient temperature 3: AcOH-6M HCl / 0.5 h / 85 °C View Scheme

[1-13C]D-glucose (40762-22-9) → C34(13)CH38O6

Conditions	Yield
Multi-step reaction with 2 steps 1: acetyl chloride / 70 °C 2: NaH, tetrabutylammonium iodide / dimethylformamide / Ambient temperature View Scheme

[1-13C]D-glucose (40762-22-9) → 2,3,4,6,2',3',4',6'-octa-O-benzyl-(1,1'-13C)-α,β-trehalose (89139-98-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: acetyl chloride / 70 °C 2: NaH, tetrabutylammonium iodide / dimethylformamide / Ambient temperature 3: AcOH-6M HCl / 0.5 h / 85 °C 4: 65 percent / trifluoromethanesulfonic anhydride / CH2Cl2 / 0.58 h / 20 °C View Scheme

[1-13C]D-glucose (40762-22-9) → 2,3,4,6,2',3',4',6'-octa-O-benzyl-(1,1'-13C)-α,α-trehalose (89139-98-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: acetyl chloride / 70 °C 2: NaH, tetrabutylammonium iodide / dimethylformamide / Ambient temperature 3: AcOH-6M HCl / 0.5 h / 85 °C 4: 32 percent / trifluoromethanesulfonic anhydride / CH2Cl2 / 0.58 h / 20 °C View Scheme

O-(2-(2-[2-(2-tritylsulfanylethoxy)ethoxy]ethoxy)ethyl)hydroxylamine (1141738-19-3) + [1-13C]D-glucose (40762-22-9) → C32(13)CH43NO9S + D-[1-(13)C]glucose (Z)-O-(2-(2-[2-(2-tritylsulfanylethoxy)ethoxy]ethoxy)ethyl)oxime + D-[1-(13)C]glucose (E)-O-(2-(2-[2-(2-tritylsulfanylethoxy)ethoxy]ethoxy)ethyl)oxime

Conditions	Yield
With acetic acid In water; acetonitrile at 20℃; for 16h; optical yield given as %de;

[1-13C]D-glucose (40762-22-9) → glycolic Acid (79-14-1) + D-glyceric acid (473-81-4, 600-19-1, 6000-40-4, 28305-26-2) + D-erythronic acid (488-16-4) + C(13)CH2O4 (276672-31-2)

Conditions	Yield
With sodium hydroxide; sulfuric acid; ozone In water at 20℃; pH=2.5;

[1-13C]D-glucose (40762-22-9) → D-Arabinose (10323-20-3) + arabinoic acid (488-30-2) + C3(13)CH6O6 (1185549-46-5) + C5(13)CH10O6 (1185549-13-6) + C5(13)CH12O7 (153474-36-3) + C5(13)CH10O7 (1185548-95-1) + C5(13)CH10O7 (1185549-04-5) + C5(13)CH10O7 + D-[1-13C]-glucaric acid (1185549-29-4) + D-Xylonic acid-1-(13)C

Conditions	Yield
With sodium hydroxide; sulfuric acid; ozone In water at 20℃; pH=2.5;

...Expand

[1-13C]D-glucose (40762-22-9) + L-Lysine hydrochloride (657-27-2, 10098-89-2) + 1,2-diamino-benzene (95-54-5) → <2-hydroxymethyl-3-methylquinoxaline> (7044-17-9) + C7(13)CH6N2 + C10H10N2O2 + C11(13)CH14N2O3 + C11(13)CH14N2O3 + C11(13)CH14N2O4 + C17(13)CH26N4O4 + <(1'S)-2-(1',2'-dihydroxyethyl)-3-methylquinoxaline> + <(2'S)-2-(2',3',4'-trihydroxybutyl)quinoxaline> + <2-(2'-hydroxyethyl)quinoxaline> (30093-23-3)

Conditions	Yield
With diethylenetriaminopentaacetic acid at 50℃; for 168h; pH=7.4; Mechanism; aq. phosphate buffer; Inert atmosphere;

...Expand

[1-13C]D-glucose (40762-22-9) → C8(13)C7H14O5 (1270036-45-7)

Conditions	Yield
With Sesamum indicum hairy root culture In water for 336h;

[1-13C]D-glucose (40762-22-9) → D-[1-13C]-glucaric acid (1185549-29-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: nitric acid; sodium nitrite / 20 - 60 °C 1.2: 1 h / 0 °C / pH 10 - 11 1.3: pH 3.5 2.1: Dowex 50WX8-100 (H+) / water / 0.08 h View Scheme

Upstream product

• 10323-20-3 D-Arabinose 
• 40010-55-7 α- and β-D-<1-13C>mannose 
• 70849-31-9 <1-13C>-D-mannose 

Downstream Products

• 132144-93-5 D-(1-13C)glucitol 
• 478506-38-6 C₅⁽¹³⁾CH₁₂O₆ 
• 108311-21-3 <1-13C>-D-fructose 
• 444313-77-3 C₁-¹³C-tri-O-benzyl-D-glucal 
• 57-48-7 fructose 
• 1633-56-3 (¹³C)-formic acid 
• 57-55-6 propylene glycol 
• 110-62-3 pentanal 
• 1563-80-0 (2-¹³C)acetic acid 
• 64-17-5 ethanol 
• 116-09-6 hydroxy-2-propanone 
• 64-18-6 formic acid 
• 96-26-4 dihydroxyacetone 
• 141-46-8 Glycolaldehyde 

Relevant articles and documents

HYDROXIDE-CATALYZED ISOMERIZATION OF D-(1-13C)MANNOSE: EVIDENCE FOR THE INVOLVEMENT OF 3,4-ENEDIOLS

The KOH-catalyzed isomerization of D-(1-13C)mannose under anaerobic conditions was studied by 13C-n.m.r. spectroscopy.D-(1-13C)Glucose and D-(1-13C)fructose are generated during the reaction, as expected.In addition, however, (6-13C)glucose, (6-13C)mannose, and (6-13C)fructose are produced in small proportions, possibly via symmetrical 3,4-enediol intermediates.The involvement of the latter structures in 13C-label shifting is inferred from the observation of (1-13C)sorbose and (6-13C)sorbose in the reaction mixture.