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L-Glucose is an enantiomer of the more common D-glucose, a naturally occurring carbohydrate used in various cellular processes. Unlike 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 have been identified that contain NAD+-dependent L-glucose dehydrogenases capable of oxidizing L-glucose.

921-60-8

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921-60-8 Usage

Uses

Used in Pharmaceutical Industry:
L-Glucose is used as a synthetic sugar for the formation of L-Glucose Pentaacetate, a potential therapeutic agent for type II diabetes. It helps in the development of treatments for this metabolic disorder.
Used in Medical Procedures:
L-Glucose is used as a colon cleansing agent before a colonoscopy procedure. It aids in the preparation of the colon for examination and diagnosis.
Used in Research:
L-Glucose has been used in phospho-buffered saline (PBS) solution to induce metabolic responses in Saccharomyces cerevisiae, a model organism for studying cellular processes. It is also used to study the substrate competition pattern of IICB glucose transporter, contributing to the understanding of glucose transport mechanisms.

Check Digit Verification of cas no

The CAS Registry Mumber 921-60-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,2 and 1 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 921-60:
(5*9)+(4*2)+(3*1)+(2*6)+(1*0)=68
68 % 10 = 8
So 921-60-8 is a valid CAS Registry Number.
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

921-60-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name aldehydo-L-glucose

1.2 Other means of identification

Product number -
Other names D-(+)-ALTROSE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:921-60-8 SDS

921-60-8Synthetic route

2,3:4,5-di-O-isopropylidene-D-gulose

2,3:4,5-di-O-isopropylidene-D-gulose

L-glucose
921-60-8

L-glucose

Conditions
ConditionsYield
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

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

L-glucose

Conditions
ConditionsYield
With mercaptoethyl alcohol; Tris*HCl buffer; manganese(ll) chloride; fucose isomerase at 25℃; for 72h;28.9%
6'-O-(3''-O-methylgalloyl)arbutin

6'-O-(3''-O-methylgalloyl)arbutin

A

D-glucose
50-99-7

D-glucose

B

L-glucose
921-60-8

L-glucose

Conditions
ConditionsYield
With hydrogenchloride In water at 90℃; for 1h;A 26%
B n/a
L-arabinose
5328-37-0

L-arabinose

L-glucose
921-60-8

L-glucose

Conditions
ConditionsYield
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

1-Desoxy-1-nitro-L-gluco-hexitol

L-glucose
921-60-8

L-glucose

Conditions
ConditionsYield
With sodium hydroxide beim anschliessend mit wss.Schwefelsaeure;
(2S,3R,4S,5S)-6-Benzhydryloxy-2,3,4,5-tetrahydroxy-hexanal

(2S,3R,4S,5S)-6-Benzhydryloxy-2,3,4,5-tetrahydroxy-hexanal

L-glucose
921-60-8

L-glucose

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol Yield given;
L-gluconic acid-lactone

L-gluconic acid-lactone

L-glucose
921-60-8

L-glucose

Conditions
ConditionsYield
With sodium amalgam; sulfuric acid
With sodium amalgam; sodium hydrogen oxalate
L-gluconic acid
157663-13-3

L-gluconic acid

sodium amalgam

sodium amalgam

L-glucose
921-60-8

L-glucose

Conditions
ConditionsYield
das Lacton reagiert;
L-glucono-1,5-lactone
52153-09-0

L-glucono-1,5-lactone

γ lactone of/the/ l-gluconic acid
74464-44-1

γ lactone of/the/ l-gluconic acid

L-glucose
921-60-8

L-glucose

Conditions
ConditionsYield
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

2-hydroxybenzoyl-β-L-glucopyranosyl (2->1)-β-L-glucopyranosyl (2->1)-β-L-glucopyranosyl (2->1) β-Lglucopyranoside

A

L-glucose
921-60-8

L-glucose

B

salicylic acid
69-72-7

salicylic acid

Conditions
ConditionsYield
Acidic conditions;
2-(hydroxymethyl)-4-oxo-4Hpyran-3-yl 3-O-β-D-glucopyranosyl-β-D-glucopyranoside

2-(hydroxymethyl)-4-oxo-4Hpyran-3-yl 3-O-β-D-glucopyranosyl-β-D-glucopyranoside

A

D-glucose
50-99-7

D-glucose

B

L-glucose
921-60-8

L-glucose

Conditions
ConditionsYield
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

2-methyl-4-oxo-4H-pyran-3-yl 3-O-β-D-glucopyranosyl-β-D-glucopyranoside

A

D-glucose
50-99-7

D-glucose

B

L-glucose
921-60-8

L-glucose

Conditions
ConditionsYield
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

2-(hydroxymethyl)-4-oxo-4H-pyran-3-yl 6-O-β-D-glucopyranosyl-β-D-glucopyranoside

A

D-glucose
50-99-7

D-glucose

B

L-glucose
921-60-8

L-glucose

Conditions
ConditionsYield
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

2-methyl-4-oxo-4H-pyran-3-yl 6-O-β-D-glucopyranosyl-β-D-glucopyranoside

A

D-glucose
50-99-7

D-glucose

B

L-glucose
921-60-8

L-glucose

Conditions
ConditionsYield
With trifluoroacetic acid In pyridine at 120℃; for 1h; Inert atmosphere;
2,3:4,5-di-O-isopropylidene-L-glucitol

2,3:4,5-di-O-isopropylidene-L-glucitol

L-glucose
921-60-8

L-glucose

Conditions
ConditionsYield
With Dowex In water for 24h;14.8 g
sodium α-d-glucoheptonatehydrate
13007-85-7

sodium α-d-glucoheptonatehydrate

L-glucose
921-60-8

L-glucose

Conditions
ConditionsYield
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

methyl 2,3:4,5:6,7-tri-O-isopropylidene-D-glycero-D-gulo-heptonate

L-glucose
921-60-8

L-glucose

Conditions
ConditionsYield
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

methyl 2,3:4,5-di-O-isopropylidene-D-glycero-D-gulo-heptonate

L-glucose
921-60-8

L-glucose

Conditions
ConditionsYield
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

3-O-β-D-glucopyranosyl-hederagenin 23-O-α-D-ribofuranoside

A

D-ribose
50-69-1

D-ribose

B

L-ribose
24259-59-4

L-ribose

C

D-glucose
50-99-7

D-glucose

D

L-glucose
921-60-8

L-glucose

Conditions
ConditionsYield
With trifluoroacetic acid In water at 120℃; for 4h;
isovitexin-6''-O-α-L-glucopyranoside

isovitexin-6''-O-α-L-glucopyranoside

A

D-glucose
50-99-7

D-glucose

B

L-glucose
921-60-8

L-glucose

C

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
520-36-5

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

Conditions
ConditionsYield
With hydrogenchloride; water at 90℃; for 3h;
cellobiose

cellobiose

L-glucose
921-60-8

L-glucose

Conditions
ConditionsYield
With water
(1R,5R,6R,7R,8S,11S)-11,13-dihydrodehydrocostuslactone-8-O-6’-2’’(E)-butenoyl-β-D-glucopyranoside

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

L-glucose
921-60-8

L-glucose

Conditions
ConditionsYield
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

3,3',5'-trimethoxylmyricetin 7-O-β-D–glucopyranoside

A

D-glucose
50-99-7

D-glucose

B

L-glucose
921-60-8

L-glucose

Conditions
ConditionsYield
With hydrogenchloride In water at 105℃; for 4h;
3-(4-hydroxy-3-methoxyphenyl)propyl-1-O-[β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside]

3-(4-hydroxy-3-methoxyphenyl)propyl-1-O-[β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside]

B

D-glucose
50-99-7

D-glucose

C

L-glucose
921-60-8

L-glucose

Conditions
ConditionsYield
With water Acidic conditions;
L-glucose
921-60-8

L-glucose

L-gluconic acid
157663-13-3

L-gluconic acid

Conditions
ConditionsYield
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

L-glucose

2-{5-[5-C-(1,4-anhydro-β-D-erythrotetrofuranosyl)-2-methylfuran-3-yl]-1,3,4-oxadiazol-2-ylthio}acetohydrazide
1338470-77-1

2-{5-[5-C-(1,4-anhydro-β-D-erythrotetrofuranosyl)-2-methylfuran-3-yl]-1,3,4-oxadiazol-2-ylthio}acetohydrazide

D-glucose 2-{5-[5-(1,4-anhydro-β-D-erythrotetrofuranosyl)-2-methylfuran-3-yl]-1,3,4-oxadiazol-2-ylthio}acetohydrazone

D-glucose 2-{5-[5-(1,4-anhydro-β-D-erythrotetrofuranosyl)-2-methylfuran-3-yl]-1,3,4-oxadiazol-2-ylthio}acetohydrazone

Conditions
ConditionsYield
With acetic acid In ethanol; water Reflux;78%
L-glucose
921-60-8

L-glucose

A

L-gluconic acid
157663-13-3

L-gluconic acid

B

ketogulonic acid
5627-26-9

ketogulonic acid

Conditions
ConditionsYield
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-glucose

A

L-gluconic acid
157663-13-3

L-gluconic acid

B

5-ketogluconic acid
488-34-6

5-ketogluconic acid

C

ketogulonic acid
5627-26-9

ketogulonic acid

Conditions
ConditionsYield
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

L-glucose

N-<4,6-bis(dimethylamino)-1,3,5-triazin-2-yl>trimethylammonium chloride
33949-42-7

N-<4,6-bis(dimethylamino)-1,3,5-triazin-2-yl>trimethylammonium chloride

2-O-<4,6-bis(dimethylamino)-1,3,5-triazin-2-yl>-β-L-glucopyranoside

2-O-<4,6-bis(dimethylamino)-1,3,5-triazin-2-yl>-β-L-glucopyranoside

Conditions
ConditionsYield
With potassium hydroxide In water 1.) 0 deg C, 2 h, 2.) 25 deg C, 12 h;27%
pyridine
110-86-1

pyridine

L-glucose
921-60-8

L-glucose

acetic anhydride
108-24-7

acetic anhydride

α/β‐L‐glucopyranosyl‐1,2,3,4,5‐pentaacetate
147648-81-5

α/β‐L‐glucopyranosyl‐1,2,3,4,5‐pentaacetate

Conditions
ConditionsYield
at 0℃;
Acetyl bromide
506-96-7

Acetyl bromide

L-glucose
921-60-8

L-glucose

2,3,4,6-tetra-O-acetyl-α-L-glucopyranosyl bromide
67337-79-5

2,3,4,6-tetra-O-acetyl-α-L-glucopyranosyl bromide

Conditions
ConditionsYield
With acetic acid
L-glucose
921-60-8

L-glucose

phenylhydrazine acetate
72358-76-0

phenylhydrazine acetate

lyxo-[2]Hexosulose-bis-phenylhydrazon
23275-67-4

lyxo-[2]Hexosulose-bis-phenylhydrazon

Conditions
ConditionsYield
With water phenyl-l-fructosazone;
L-glucose
921-60-8

L-glucose

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

O4,O6-((S)-ethylidene)-L-glucose

Conditions
ConditionsYield
With sulfuric acid; paracetaldehyde
Conditions
ConditionsYield
With sulfuric acid; copper(II) sulfate; acetone
L-glucose
921-60-8

L-glucose

sodium acetate
127-09-3

sodium acetate

acetic anhydride
108-24-7

acetic anhydride

α/β‐L‐glucopyranosyl‐1,2,3,4,5‐pentaacetate
66966-07-2

α/β‐L‐glucopyranosyl‐1,2,3,4,5‐pentaacetate

L-glucose
921-60-8

L-glucose

1,1-Diphenylhydrazine
530-50-7

1,1-Diphenylhydrazine

glucose-diphenylhydrazone
5149-20-2, 5149-24-6, 5149-25-7

glucose-diphenylhydrazone

Conditions
ConditionsYield
With ethanol at 100℃; im geschlossenen Rohr; -diphenylhydrazone;
L-glucose
921-60-8

L-glucose

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

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

[(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

[(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
ConditionsYield
With ammonium chloride In ethanol for 4h; Heating;
L-glucose
921-60-8

L-glucose

L-(-)-α-methylbenzylamine
2627-86-3

L-(-)-α-methylbenzylamine

acetic anhydride
108-24-7

acetic anhydride

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

Acetic acid (1S,2S,3S)-2,3,4-triacetoxy-1-{(R)-1-acetoxy-2-[acetyl-(1-phenyl-ethyl)-amino]-ethyl}-butyl ester

Conditions
ConditionsYield
With pyridine; sodium cyanoborohydride 1.) methanol-water 2.) 100 deg C, 1 h; Multistep reaction;
L-glucose
921-60-8

L-glucose

(-)-α-methylbenzylamine
2627-86-3

(-)-α-methylbenzylamine

acetic anhydride
108-24-7

acetic anhydride

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

Acetic acid (1S,2S,3S)-2,3,4-triacetoxy-1-{(R)-1-acetoxy-2-[acetyl-((S)-1-phenyl-ethyl)-amino]-ethyl}-butyl ester

Conditions
ConditionsYield
With pyridine; sodium cyanoborohydride 1.)Methanol, water, room temp. 2.)100 deg C, 1 hour; Multistep reaction;
L-glucose
921-60-8

L-glucose

p-toluidine
106-49-0

p-toluidine

N-(p-tolyl)-amine-1-D-fructose
61819-68-9

N-(p-tolyl)-amine-1-D-fructose

Conditions
ConditionsYield
With acetic acid In water for 0.5h; Heating;
L-glucose
921-60-8

L-glucose

2,2'-bipyridine-4,4'-diboronic acid
159614-36-5

2,2'-bipyridine-4,4'-diboronic acid

C10H10B2N2O4*C6H12O6

C10H10B2N2O4*C6H12O6

Conditions
ConditionsYield
complex formation;
L-glucose
921-60-8

L-glucose

Sucrose
57-50-1

Sucrose

A

leucrose (5-O-α-D-glucopyranosyl-β-D-fructopyranose)
470-16-6, 58166-26-0, 100430-38-4, 130853-03-1, 7158-70-5

leucrose (5-O-α-D-glucopyranosyl-β-D-fructopyranose)

B

α-D-glucopyranosyl-(1->6)-α-D-glucopyranosyl-(1->4)-L-glucose

α-D-glucopyranosyl-(1->6)-α-D-glucopyranosyl-(1->4)-L-glucose

Conditions
ConditionsYield
With alternansucrase from Leuconostoc mesenteroides NRRL B-21297 Enzymatic reaction;
L-glucose
921-60-8

L-glucose

dimethyl amine
124-40-3

dimethyl amine

C8H17NO5

C8H17NO5

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

921-60-8Relevant academic research and scientific papers

A new sesquiterpenoid glycoside from Saussurea involucrata

Qi, Shizhou,Yang, Yiren,Xian, Xiaoyan,Li, Xianzhe,Gao, Huiyuan

, p. 943 - 949 (2020)

Saussurea involucrata, known for the abundant bioactive components, is a precious traditional Chinese medicine. In this study, a novel guaiane sesquiterpenoid glycoside named (1R, 5R, 6R, 7R, 8S, 11S)-11, 13-dihydrodehydrocostuslactone-8-O-6'-2''(E)-butenoyl-β-D-glucopyranoside (1), together with seven known compounds (2–8) were isolated from the dried aerial part of S. involucrata. Their structures were elucidated by spectroscopic and physico-chemical analyses. The antioxidant and anti-inflammatory activities of compound 1 were investigated. And compound 1 showed weak radical scavenging activity and low inhibitory activity on nitric oxide (NO) production.

Porous structured CuO-CeO2 nanospheres for the direct oxidation of cellobiose and glucose to gluconic acid

Amaniampong, Prince Nana,Trinh, Quang Thang,Li, Kaixin,Mushrif, Samir H.,Hao, Yu,Yang, Yanhui

, p. 172 - 182 (2018)

Porous-structured CuO-CeO2 nanospheres were synthesized using a hydrothermal method and were tested as catalysts for the direct oxidation of cellobiose to gluconic acid. Catalytic reaction along with catalyst characterization results and 18O-oxygen isotope labeled experiments revealed that the surface lattice oxygen of CuO in CuO-CeO2 nanospheres was consumed during the oxidation of cellobiose. This provides a direct evidence of our previous work (Amaniampong et al., Angew. Chem. Int. Ed. 54 (2015) 8928–8933). Characterization results further suggested that the lattice oxygen in CeO2 did not participate in the oxidation; nonetheless, the addition of CeO2 to CuO enhanced the surface area of the catalyst composite which was crucial for the reaction. The spent catalyst upon re-oxidation regained its activity. In addition, isotope labeled deuterium oxide (D2O) experiments suggested that hydrogen exchange between the solvent and the substrate (glucose) are not involved in the mechanistic formation of gluconic acid and confirmed the solvent had no direct influence in the formation of gluconic acid.

Three new compounds from the twigs and leaves of Nageia fleuryi Hickel

Chen, Lu-Zhou,Liu, Yu-Nan,Lou, Hong-Xiang,Ren, Dong-Mei,Shen, Tao,Wang, Xiao-Ning,Xiang, Lan,Xu, Jia-Xin,Yang, Hu

supporting information, (2022/03/31)

Two new diterpenoids, 12,15-di-O-acetylhypargenin B (1) and taiwanin F-12-O-β-D-glucopyranoside (2), one new monoterpenoid, (S)-7-methyl-3-methyleneoct-6-ene-1,2-diyl diacetate (3), together with eight known compounds (4?11), were obtained from the twigs

Isolation, structural elucidation and molecular docking studies against SARS-CoV-2 main protease of new stigmastane-type steroidal glucosides isolated from the whole plants of Vernonia gratiosa

Anh, Hoang Le Tuan,Anh, Le Tuan,Lee, Ki Yong,Phong, Nguyen Viet,Quang Minh, Bui,Trang, Nguyen Minh,Trung, Nguyen Quang,Van Cong, Pham,Van Dan, Nguyen,Viet Duc, Ngo,Vinh, Le Ba

supporting information, (2022/02/22)

Phytochemical investigation of the whole plants of Vernonia gratiosa Hance. led in the isolation and identification of two new stigmastane-type steroidal glucosides (1–2), namely vernogratiosides A (1), and B (2). Their chemical structures were fully elucidated based on 1 D/2D NMR spectroscopic, HR-ESI-MS data analyses, and by producing derivatives by chemical reactions. The binding potential of the isolated compounds to replicase protein ? main protease of SARS-CoV-2 were examined using the molecular docking simulations. Our results show that the isolated steroidal glucosides (1–2) bind to the substrate‐binding site of SARS-CoV-2 main protease with binding affinities of ?7.2 and ?7.6 kcal/mol, respectively, as well as binding abilities equivalent to N3 inhibitor that has already been reported (–7.5 kcal/mol).

Phenolic glycosides and flavonoids with antioxidant and anticancer activities from Desmodium caudatum

Xu, Qian-Nan,Zhu, Dan,Wang, Guang-Hui,Lin, Ting,Sun, Cui-Ling,Ding, Rong,Tian, Wen-Jing,Chen, Hai-Feng

, p. 4534 - 4541 (2020/03/23)

Descaudatine A (1), an undescribed phenolic glycoside, along with a known analogue (2) and ten flavonoids (3-12), were isolated from the whole plant of Desmodium caudatum. Compounds 1 and 4 exhibited potent antioxidant activities with the IC50 of 58.59 μM and 31.31 μM, respectively, which were approached to that of the positive control Vitamin C (IC50 = 46.32 μM). Meanwhile, 12 showed moderate antioxidant activity with the IC50 of 173.9 μM. Besides, compounds 3 and 6 inhibited the proliferation of HeLa cells with IC50 values of 56.14 μM and 69.04 μM, respectively. Further studies indicated that 3 and 6 could dose-dependently induce PARP cleavage and might trigger caspase-3, 8, 9 activation to induce apoptosis. RXRα is an ideal anticancer target of nuclear receptor. The reporter gene assay of RXRα indicated that 3 and 6 could inhibited the 9-cis-RA induced RXRα transcription in a concentration-dependent manner.

Orthogonal Active-Site Labels for Mixed-Linkage endo-β-Glucanases

Jain, Namrata,Tamura, Kazune,Déjean, Guillaume,Van Petegem, Filip,Brumer, Harry

, p. 1968 - 1984 (2021/05/26)

Small molecule irreversible inhibitors are valuable tools for determining catalytically important active-site residues and revealing key details of the specificity, structure, and function of glycoside hydrolases (GHs). β-glucans that contain backbone β(1,3) linkages are widespread in nature, e.g., mixed-linkage β(1,3)/β(1,4)-glucans in the cell walls of higher plants and β(1,3)glucans in yeasts and algae. Commensurate with this ubiquity, a large diversity of mixed-linkage endoglucanases (MLGases, EC 3.2.1.73) and endo-β(1,3)-glucanases (laminarinases, EC 3.2.1.39 and EC 3.2.1.6) have evolved to specifically hydrolyze these polysaccharides, respectively, in environmental niches including the human gut. To facilitate biochemical and structural analysis of these GHs, with a focus on MLGases, we present here the facile chemo-enzymatic synthesis of a library of active-site-directed enzyme inhibitors based on mixed-linkage oligosaccharide scaffolds and N-bromoacetylglycosylamine or 2-fluoro-2-deoxyglycoside warheads. The effectiveness and irreversibility of these inhibitors were tested with exemplar MLGases and an endo-β(1,3)-glucanase. Notably, determination of inhibitor-bound crystal structures of a human-gut microbial MLGase from Glycoside Hydrolase Family 16 revealed.

Anti-inflammatory active components of the roots of Datura metel

Qin, Ze,Zhang, Jin,Chen, Liang,Liu, Shu-Xiang,Zhao, Hai-Feng,Mao, Hui-Min,Zhang, Hong-Yang,Li, De-Fang

, p. 392 - 398 (2020/03/30)

One new phenolic glycoside, methyl 3,4-dihydroxyphenylacetate-4-O-[2-O-β-D-apisoyl-6-O-(2-hydroxybenzoyl)]-β-D-glucopyranoside (1), together with 10 known compounds (2–11), were isolated from the roots of Datura metel. The structures of these compounds we

A new triterpenoid and a new flavonoid glycoside isolated from Bupleurum marginatum and their anti-inflammatory activity

Lei, Zhiqiang,Zou, Guoming,Gao, Ying,Yao, Yuqiao,Peng, Caiying,Shu, Jicheng,Yang, Ming

supporting information, p. 3492 - 3498 (2019/03/26)

This study to investigate chemical constituents from the aerial of Bupleurum marginatum led to the isolation of a new trierpenoid and a new flavonoid, namely 3β-hydroxy-cycloart-24-en-26-acetyloxy (1), and 3, 3′, 5′-trimethoxyl-myricetin 7-O-β-D–glucopyranoside (2) along with eight known compounds (3–10). Their structures were established by spectral data analyses (MS, 1D and 2D NMR), as well as by comparison of spectral data with those of the related known compounds. The 24-en-lanostane type triterpenoid with a cyclopropane ring (1 and 3) was firstly reported from this specie, which might be chemotaxonomic markers of this specie. In addition, compounds 1 and 2 were examined for their anti-inflammatory activity. Compounds 1 and 2 inhibited the NF κB induction by 60.61% and 24.30%.

Method for preparing lactic acid through catalytically converting carbohydrate

-

Paragraph 0029-0040, (2020/11/01)

The invention relates to a method for preparing lactic acid through catalytically converting carbohydrate, and in particular, relates to a process for preparing lactic acid by catalytically convertingcarbohydrate under hydrothermal conditions. The method disclosed by the invention is characterized by specifically comprising the following steps: 1) adding carbohydrate and a catalyst into a closedhigh-pressure reaction kettle, and then adding pure water for mixing; 2) introducing nitrogen into the high-pressure reaction kettle to discharge air, introducing nitrogen of 2 MPa, stirring and heating to 160-300 DEG C, and carrying out reaction for 10-120 minutes; 3) putting the high-pressure reaction kettle in an ice-water bath, and cooling to room temperature; and 4) filtering the solution through a microporous filtering membrane to obtain the target product. The method can realize high conversion rate of carbohydrate and high yield of lactic acid, and has the advantages of less catalyst consumption, good circularity, small corrosion to reaction equipment and the like.

Chemical constituents of Bergenia crassifolia roots and their growth inhibitory activity against Babesia bovis and B. bigemina

Banzragchgarav, Orkhon,Murata, Toshihiro,Tuvshintulga, Bumduuren,Suganuma, Keisuke,Igarashi, Ikuo,Inoue, Noboru,Batkhuu, Javzan,Sasaki, Kenroh

, p. 79 - 83 (2018/11/25)

Bergenia crassifolia is a tea plant from in Northeast Asia, and it used to be a traditional medicine in Asian countries. From the roots of this plant, two new compounds, (2R,3S)-3-O-p-hydroxybenzoyl-5-O-galloylcatechin and 6-O-(3′′-O-methylgalloyl) arbutin, were isolated together with 20 known flavonoids, including catechins, kaemferols, arbutin derivatives, and bergenin derivatives. Their chemical structures were elucidated on the basis of spectroscopic data analyses. The anti-babesial activities of the isolated compounds were estimated using in vitro tests against Babesia bigemina and B. bovis, which are the most prevalent species associated with bovine babesiosis. The compounds with galloyl groups showed moderate growth-inhibition effects on B. bovis (IC50 0.80–10.3 μg/mL) and B. bigemina (IC50 5.69–8.60 μg/mL).

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