921-60-8

Basic information

• Product Name: L-GLUCOSE
• Synonyms: L(-)-Glucose,98%;(2S,3R,4S,5S)-2,3,4,5,6-pentahydroxyhexanal;L-Glucose 99%;L(-)-Glucose, 98% 250MG;l-[1,2,3-13C3]glucose;l-[1,2-13C2]glucose;l-[3-13C]glucose;l-[UL-13C6]glucose
• CAS NO: 921-60-8
• Molecular Formula: C₆H₁₂O₆
• Molecular Weight: 180.16
• EINECS: 213-068-3
• Product Categories: Basic Sugars (Mono & Oligosaccharides);Biochemistry;Glucose;Sugars;Carbohydrates;Carbohydrates A to;Carbohydrates GBiochemicals and Reagents;Monosaccharide;carbohydrate
• Mol File: 921-60-8.mol
• Article Data: 38

Chemical Properties

• Melting Point: 153-156 °C(lit.)
• Boiling Point: 232.96°C (rough estimate)
• Flash Point: 202.2 ºC
• Appearance: White/aqueous ethanol solution
• Density: 1.2805 (rough estimate)
• Vapor Pressure: 1.83E-08mmHg at 25°C
• Refractive Index: -52 ° (C=5, H2O)
• Storage Temp.: 2-8°C
• Solubility: H2O: 0.1 g/mL, clear, colorless
• PKA: 12.45±0.20(Predicted)
• Water Solubility: Soluble in water, alcohol.
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• Merck: 14,4459
• BRN: 1724626
• CAS DataBase Reference: L-GLUCOSE(CAS DataBase Reference)
• NIST Chemistry Reference: L-GLUCOSE(921-60-8)
• EPA Substance Registry System: L-GLUCOSE(921-60-8)

Safety Data

• Hazard Codes: F,Xi,R,Xn
• Statements: 11-36/37/38-63-62-46-36/38-21
• Safety Statements: 16-26-36-53-36/37-25
• RIDADR: UN 2910 7
• WGK Germany: 3
• RTECS: LZ6610000
• F: 3
• Hazardous Substances Data: 921-60-8(Hazardous Substances Data)

Usage

Description

L-(?)-Glucose is an enantiomer of the more common D-glucose. L-Glucose is not bioavailable to cells as an energy source because it cannot be phosphorylated by hexokinase. However, certain L-glucose-utilizing bacteria that contain NAD+-dependent L-glucose dehydrogenases capable of oxidizing L-glucose have been identified.

Chemical Properties

white powder

Uses

Different sources of media describe the Uses of 921-60-8 differently. You can refer to the following data:
1. L-Glucose is the enantiomer of D-Glucose (G595000), a naturally occurring carbohydrate used in an abundance of cellular processes. L-Glucose is a synthetic sugar used in the formation of L-Glucose Pen taacetate (G596510), a potential therapeutic agent regarding type II diabetes. In addition, L-glucose can be used as a colon cleansing agent for before a colonoscopy procedure.
2. L-(-)-Glucose is an enantiomer of the more common D-glucose a naturally occurring carbohydrate used in an abundance of cellular processes. L-Glucose is a synthetic sugar used in the formation of L-Glucose Pen taacetate, a potential therapeutic agent regarding type II diabetes. In addition, L-glucose can be used as a colon cleansing agent for before a colonoscopy procedure.
3. L-(-)-Glucose has been used in phospho-buffered saline (PBS) solution to induce metabolic responses in Saccharomyces cerevisiae. It has also been used to study the substrate competition pattern of IICB glucose transporter.

Definition

ChEBI: The L-enantiomer of aldehydo-glucose.

General Description

L-(?)-Glucose is an enantiomer of the more common D-glucose. L-Glucose cannot be used by cells as an energy source because it cannot be phosphorylated by hexokinase.

InChI:InChI=1/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6-/m0/s1

Synthetic route

2,3:4,5-di-O-isopropylidene-D-gulose → L-glucose (921-60-8)

Conditions	Yield
With DOWEX(α)50WX8-200 In water at 20℃; for 48h;	100%

2-Chloro-9-((3aR,4R,6R,6aR)-2,2,3a,6-tetramethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-ylamine → L-glucose (921-60-8)

Conditions	Yield
With mercaptoethyl alcohol; Tris*HCl buffer; manganese(ll) chloride; fucose isomerase at 25℃; for 72h;	28.9%

6'-O-(3''-O-methylgalloyl)arbutin → D-glucose (50-99-7) + L-glucose (921-60-8)

Conditions	Yield
With hydrogenchloride In water at 90℃; for 1h;	A 26% B n/a

L-arabinose (5328-37-0) → L-glucose (921-60-8)

Conditions	Yield
With pyridine; hydrogen cyanide Beim Behandeln des Reaktionsprodukts mit wss.Salzsaeure unter gleichzeitigem Hydrieren an Palladium/Bariumsulfat;
Multi-step reaction with 2 steps 1: sodium methylate 2: aqueous NaOH-solution / beim anschliessend mit wss.Schwefelsaeure View Scheme

1-Desoxy-1-nitro-L-gluco-hexitol (69257-51-8) → L-glucose (921-60-8)

Conditions	Yield
With sodium hydroxide beim anschliessend mit wss.Schwefelsaeure;

(2S,3R,4S,5S)-6-Benzhydryloxy-2,3,4,5-tetrahydroxy-hexanal → L-glucose (921-60-8)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol Yield given;

L-gluconic acid-lactone → L-glucose (921-60-8)

Conditions	Yield
With sodium amalgam; sulfuric acid
With sodium amalgam; sodium hydrogen oxalate

L-gluconic acid (157663-13-3) + sodium amalgam → L-glucose (921-60-8)

Conditions	Yield
das Lacton reagiert;

L-glucono-1,5-lactone (52153-09-0) + γ lactone of/the/ l-gluconic acid (74464-44-1) → L-glucose (921-60-8)

Conditions	Yield
Stage #1: L-glucono-1,5-lactone; γ lactone of/the/ l-gluconic acid With sodium tetrahydroborate In water at -5 - 5℃; for 0.333333h; Stage #2: With acetic acid In water

2-hydroxybenzoyl-β-L-glucopyranosyl (2->1)-β-L-glucopyranosyl (2->1)-β-L-glucopyranosyl (2->1) β-Lglucopyranoside (1351356-85-8) → L-glucose (921-60-8) + salicylic acid (69-72-7)

Conditions	Yield
Acidic conditions;

2-(hydroxymethyl)-4-oxo-4Hpyran-3-yl 3-O-β-D-glucopyranosyl-β-D-glucopyranoside → D-glucose (50-99-7) + L-glucose (921-60-8)

Conditions	Yield
With trifluoroacetic acid In pyridine at 120℃; for 1h; Inert atmosphere;

2-methyl-4-oxo-4H-pyran-3-yl 3-O-β-D-glucopyranosyl-β-D-glucopyranoside → D-glucose (50-99-7) + L-glucose (921-60-8)

Conditions	Yield
With trifluoroacetic acid In pyridine at 120℃; for 1h; Inert atmosphere;

2-(hydroxymethyl)-4-oxo-4H-pyran-3-yl 6-O-β-D-glucopyranosyl-β-D-glucopyranoside → D-glucose (50-99-7) + L-glucose (921-60-8)

Conditions	Yield
With trifluoroacetic acid In pyridine at 120℃; for 1h; Inert atmosphere;

2-methyl-4-oxo-4H-pyran-3-yl 6-O-β-D-glucopyranosyl-β-D-glucopyranoside → D-glucose (50-99-7) + L-glucose (921-60-8)

Conditions	Yield
With trifluoroacetic acid In pyridine at 120℃; for 1h; Inert atmosphere;

2,3:4,5-di-O-isopropylidene-L-glucitol → L-glucose (921-60-8)

Conditions	Yield
With Dowex In water for 24h;	14.8 g

sodium α-d-glucoheptonatehydrate (13007-85-7) → L-glucose (921-60-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: hydrogenchloride / water; methanol / 1 h / Reflux 2: sulfuric acid / water; methanol / 4.25 h / 20 °C 3: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / -40 °C / Reflux 4: SiO2-supported NaIO4 / dichloromethane / 0.5 h 5: Dowex® / water / 24 h View Scheme

methyl 2,3:4,5:6,7-tri-O-isopropylidene-D-glycero-D-gulo-heptonate (1595285-44-1) → L-glucose (921-60-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfuric acid / water; methanol / 4.25 h / 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / -40 °C / Reflux 3: SiO2-supported NaIO4 / dichloromethane / 0.5 h 4: Dowex® / water / 24 h View Scheme

methyl 2,3:4,5-di-O-isopropylidene-D-glycero-D-gulo-heptonate (1595285-46-3) → L-glucose (921-60-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / -40 °C / Reflux 2: SiO2-supported NaIO4 / dichloromethane / 0.5 h 3: Dowex® / water / 24 h View Scheme

3-O-β-D-glucopyranosyl-hederagenin 23-O-α-D-ribofuranoside (1500092-25-0) → D-ribose (50-69-1) + L-ribose (24259-59-4) + D-glucose (50-99-7) + L-glucose (921-60-8)

Conditions	Yield
With trifluoroacetic acid In water at 120℃; for 4h;

isovitexin-6''-O-α-L-glucopyranoside → D-glucose (50-99-7) + L-glucose (921-60-8) + 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (520-36-5)

Conditions	Yield
With hydrogenchloride; water at 90℃; for 3h;

cellobiose → L-glucose (921-60-8)

Conditions	Yield
With water

(1R,5R,6R,7R,8S,11S)-11,13-dihydrodehydrocostuslactone-8-O-6’-2’’(E)-butenoyl-β-D-glucopyranoside → L-glucose (921-60-8)

Conditions	Yield
Stage #1: (1R,5R,6R,7R,8S,11S)-11,13-dihydrodehydrocostuslactone-8-O-6’-2’’(E)-butenoyl-β-D-glucopyranoside With hydrogenchloride In methanol; water for 4h; Reflux; Stage #2: With pyridine; L-cysteine methyl ester hydrochloride In methanol; water at 60℃; for 2h; Stage #3: With 2-tolyl isothiocyanate In methanol; water at 60℃; for 1h;

3,3',5'-trimethoxylmyricetin 7-O-β-D–glucopyranoside → D-glucose (50-99-7) + L-glucose (921-60-8)

Conditions	Yield
With hydrogenchloride In water at 105℃; for 4h;

3-(4-hydroxy-3-methoxyphenyl)propyl-1-O-[β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside] → D-apiose (639-97-4, 6477-44-7, 42927-70-8) + D-glucose (50-99-7) + L-glucose (921-60-8)

Conditions	Yield
With water Acidic conditions;

L-glucose (921-60-8) → L-gluconic acid (157663-13-3)

Conditions	Yield
With 1 wt% Au/TiO2; oxygen In water at 77 - 89℃; under 39547.2 Torr; Flow reactor;	94%
With CuO*CeO2 at 180℃; for 4h; Time; Reagent/catalyst; Inert atmosphere;

L-glucose (921-60-8) + 2-{5-[5-C-(1,4-anhydro-β-D-erythrotetrofuranosyl)-2-methylfuran-3-yl]-1,3,4-oxadiazol-2-ylthio}acetohydrazide (1338470-77-1) → D-glucose 2-{5-[5-(1,4-anhydro-β-D-erythrotetrofuranosyl)-2-methylfuran-3-yl]-1,3,4-oxadiazol-2-ylthio}acetohydrazone

Conditions	Yield
With acetic acid In ethanol; water Reflux;	78%

L-glucose (921-60-8) → L-gluconic acid (157663-13-3) + ketogulonic acid (5627-26-9)

Conditions	Yield
With oxygen; 1% Au 1% Pt /TiO2 In water at 62℃; under 39547.2 Torr; Temperature; Flow reactor;	A 63% B 15%

L-glucose (921-60-8) → L-gluconic acid (157663-13-3) + 5-ketogluconic acid (488-34-6) + ketogulonic acid (5627-26-9)

Conditions	Yield
With oxygen; 1% Au 1% Pt /TiO2 In water at 80℃; under 39547.2 Torr; Temperature; Flow reactor;	A 14% B 10% C 56%

L-glucose (921-60-8) + N-<4,6-bis(dimethylamino)-1,3,5-triazin-2-yl>trimethylammonium chloride (33949-42-7) → 2-O-<4,6-bis(dimethylamino)-1,3,5-triazin-2-yl>-β-L-glucopyranoside

Conditions	Yield
With potassium hydroxide In water 1.) 0 deg C, 2 h, 2.) 25 deg C, 12 h;	27%

pyridine (110-86-1) + L-glucose (921-60-8) + acetic anhydride (108-24-7) → α/β‐L‐glucopyranosyl‐1,2,3,4,5‐pentaacetate (147648-81-5)

Conditions	Yield
at 0℃;

Acetyl bromide (506-96-7) + L-glucose (921-60-8) → 2,3,4,6-tetra-O-acetyl-α-L-glucopyranosyl bromide (67337-79-5)

Conditions	Yield
With acetic acid

L-glucose (921-60-8) + phenylhydrazine acetate (72358-76-0) → lyxo-[2]Hexosulose-bis-phenylhydrazon (23275-67-4)

Conditions	Yield
With water phenyl-l-fructosazone;

L-glucose (921-60-8) → O4,O6-((S)-ethylidene)-L-glucose (112246-57-8)

Conditions	Yield
With sulfuric acid; paracetaldehyde

L-glucose (921-60-8) → 1,2:5,6-di-O-isopropylidene-α-L-glucofuranose (582-52-5, 2595-05-3, 10368-86-2, 13100-30-6, 14686-89-6, 23262-79-5, 26597-74-0, 26623-15-4, 38166-58-4, 38166-60-8, 79943-22-9, 83730-28-3)

Conditions	Yield
With sulfuric acid; copper(II) sulfate; acetone

L-glucose (921-60-8) + sodium acetate (127-09-3) + acetic anhydride (108-24-7) → α/β‐L‐glucopyranosyl‐1,2,3,4,5‐pentaacetate (66966-07-2)

L-glucose (921-60-8) + 1,1-Diphenylhydrazine (530-50-7) → glucose-diphenylhydrazone (5149-20-2, 5149-24-6, 5149-25-7)

Conditions	Yield
With ethanol at 100℃; im geschlossenen Rohr; -diphenylhydrazone;

L-glucose (921-60-8) + Amino-acetic acid (3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2,5-dihydro-furan-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester (42716-79-0) → [(2R,3S,4S,5S)-2,3,4,5,6-Pentahydroxy-hex-(E)-ylideneamino]-acetic acid (3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2,5-dihydro-furan-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester

Conditions	Yield
With ammonium chloride In ethanol for 4h; Heating;

L-glucose (921-60-8) + L-(-)-α-methylbenzylamine (2627-86-3) + acetic anhydride (108-24-7) → Acetic acid (1S,2S,3S)-2,3,4-triacetoxy-1-{(R)-1-acetoxy-2-[acetyl-(1-phenyl-ethyl)-amino]-ethyl}-butyl ester (79526-50-4, 79549-65-8, 79549-66-9, 79549-67-0, 79549-68-1, 79617-01-9, 83680-90-4, 83680-91-5)

Conditions	Yield
With pyridine; sodium cyanoborohydride 1.) methanol-water 2.) 100 deg C, 1 h; Multistep reaction;

L-glucose (921-60-8) + (-)-α-methylbenzylamine (2627-86-3) + acetic anhydride (108-24-7) → Acetic acid (1S,2S,3S)-2,3,4-triacetoxy-1-{(R)-1-acetoxy-2-[acetyl-((S)-1-phenyl-ethyl)-amino]-ethyl}-butyl ester (79526-50-4, 79549-65-8, 79549-66-9, 79549-67-0, 79549-68-1, 79617-01-9, 83680-90-4, 83680-91-5)

Conditions	Yield
With pyridine; sodium cyanoborohydride 1.)Methanol, water, room temp. 2.)100 deg C, 1 hour; Multistep reaction;

L-glucose (921-60-8) + p-toluidine (106-49-0) → N-(p-tolyl)-amine-1-D-fructose (61819-68-9)

Conditions	Yield
With acetic acid In water for 0.5h; Heating;

L-glucose (921-60-8) + 2,2'-bipyridine-4,4'-diboronic acid (159614-36-5) → C10H10B2N2O4*C6H12O6

Conditions	Yield
complex formation;

L-glucose (921-60-8) + Sucrose (57-50-1) → leucrose (5-O-α-D-glucopyranosyl-β-D-fructopyranose) (470-16-6, 58166-26-0, 100430-38-4, 130853-03-1, 7158-70-5) + α-D-glucopyranosyl-(1->6)-α-D-glucopyranosyl-(1->4)-L-glucose

Conditions	Yield
With alternansucrase from Leuconostoc mesenteroides NRRL B-21297 Enzymatic reaction;

L-glucose (921-60-8) + dimethyl amine (124-40-3) → C8H17NO5

Conditions	Yield
With acetic acid In ethanol at 20 - 75℃; for 3h; Amadori rearrangement;

Upstream product

• 69-65-8 mannitol 
• 106-42-3 para-xylene 
• 7732-18-5 water 
• 1500092-25-0 3-O-β-D-glucopyranosyl-hederagenin 23-O-α-D-ribofuranoside 
• 50-00-0 formaldehyd 
• 141-46-8 Glycolaldehyde 
• 56-81-5 glycerol 
• 926646-14-2 D-glucose-imine 
• 4990-72-1 glucosealdazine 
• 118923-30-1 D-glucitol-1-yliden-urea 
• 5160-42-9 glucose-benzoylhydrazone 
• 7647-01-0 hydrogenchloride 
• 71202-80-7 D-glucose-benzenesulfonylhydrazone 
• 100-52-7 benzaldehyde 

Downstream Products

• 3225-29-4 p-benzosemiquinone radical anion 
• 39698-24-3 tetra-O-acetyl-glucopyranosyl bromide 
• 110-15-6 succinic acid 
• 79-33-4 L-Lactic acid 
• 64-18-6 formic acid 
• 513-85-9 2.3-butanediol 
• 67-47-0 5-hydroxymethyl-2-furfuraldehyde 
• 40437-08-9 O²,O³,O⁴,O⁶-Tetraacetyl-galactose 
• 54662-27-0 1-deoxy-1-(2-hydroxyethylamino)-D-glucitol 
• 67-64-1 acetone 
• 61865-75-6 L-Altrose-dibenzyldithioacetal 
• 1941-52-2 D-glucose diethyl mercaptal 
• 74372-70-6 N-(p-hydroxyphenyl)-β-D-mannopyranosylamine 
• 31105-01-8 1-deoxy-1-<(1L)-1,3-dicarboxypropylamino>-D-fructose 

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