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58-86-6

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58-86-6 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 58-86-6 differently. You can refer to the following data:
1. white crystals or powder
2. D-Xylose is nearly odorless and has a smoky flavor.

Uses

Different sources of media describe the Uses of 58-86-6 differently. You can refer to the following data:
1. sweetener, pharmaceutical intermediate
2. An aldopentose monosaccharide.
3. In tanning, dyeing, and as a diabetic food.

Definition

Different sources of media describe the Definition of 58-86-6 differently. You can refer to the following data:
1. A SUGAR that has five carbon atoms in its molecules.
2. pentose: A sugar that has five carbonatoms per molecule.
3. ChEBI: The pyranose form of D-xylose.

General Description

Xylose is a five-carbon sugar that contributes to lignocellulose in plants. Xylose is predominantly found in hardwoods and agricultural residues.

Biochem/physiol Actions

Estimation of xylose in the urine after oral administration, is useful in diagnosing absorption of carbohydrates and malabsorption of non-pancreatic molecules. Xylose plays a significant role in the biologically conversion of plant biomass to fuels and chemicals.

Purification Methods

-D(+)-Xylose forms needles or prisms (which have a very sweet taste) by slow crystallisation from aqueous 80% EtOH or absolute EtOH, which are then dried at 60o in vacuo over P2O5. Store it in a vacuum desiccator over CaSO4. 1Gram dissolves in 0.8mL H2O. [Bragg & Hough J Chem Soc 4347 1957, Hudson & Yanovsky J Am Chem Soc 39 1029 1917, Monroe J Am Chem Soc 41 1002 1919, Beilstein 1 IV 4223.] In D2O at 31o, 1H NMR showed the following ratios: -pyranose (36.5), -pyranose (63), -furanose + -furanose (~1) [Angyal Adv Carbohydr Chem 42 15 1984, Angyal & Pickles Aust J Chem 25 1711 1972].

Check Digit Verification of cas no

The CAS Registry Mumber 58-86-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 8 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 58-86:
(4*5)+(3*8)+(2*8)+(1*6)=66
66 % 10 = 6
So 58-86-6 is a valid CAS Registry Number.
InChI:InChI=1/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4+,5+/m0/s1

58-86-6 Well-known Company Product Price

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  • Alfa Aesar

  • (A10643)  D-(+)-Xylose, 98+%   

  • 58-86-6

  • 100g

  • 289.0CNY

  • Detail
  • Alfa Aesar

  • (A10643)  D-(+)-Xylose, 98+%   

  • 58-86-6

  • 500g

  • 1047.0CNY

  • Detail
  • Alfa Aesar

  • (A10643)  D-(+)-Xylose, 98+%   

  • 58-86-6

  • 2500g

  • 4713.0CNY

  • Detail
  • USP

  • (1722005)  Xylose  United States Pharmacopeia (USP) Reference Standard

  • 58-86-6

  • 1722005-1G

  • 4,647.24CNY

  • Detail

58-86-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name aldehydo-D-xylose

1.2 Other means of identification

Product number -
Other names D-Xylose

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:58-86-6 SDS

58-86-6Synthetic route

xylan

xylan

D-xylose
58-86-6

D-xylose

Conditions
ConditionsYield
With hydrogenchloride; water at 105℃; for 3h; Ionic liquid;77%
With water at 60℃; for 3h;73 %Chromat.
xylan

xylan

A

D-xylose
58-86-6

D-xylose

B

D-lyxose
1114-34-7

D-lyxose

Conditions
ConditionsYield
With hydrogenchloride; sodium molybdate dihydrate In water for 0.05h; Sealed tube; Microwave irradiation;A 60%
B 31%
xylan

xylan

A

furfural
98-01-1

furfural

B

D-xylose
58-86-6

D-xylose

Conditions
ConditionsYield
With water In toluene at 170℃; for 6h; Inert atmosphere;A 18%
B 27%
With (2E)-but-2-enedioic acid In water at 160℃; for 4h; Reagent/catalyst; Temperature; Inert atmosphere; Autoclave; Industrial scale;A 24.4%
B 25.4%
β-D-Xylp-(1-4)-β-D-Xylp-(1-4)-β-D-Xylp-(1-4)-β-D-Xyl
22416-58-6

β-D-Xylp-(1-4)-β-D-Xylp-(1-4)-β-D-Xylp-(1-4)-β-D-Xyl

D-xylose
58-86-6

D-xylose

Conditions
ConditionsYield
With maize β-xylosidase for 6h; aq. acetate buffer; Enzymatic reaction;
With recombinant β-xylosidase/α-L-arabinofuranosidase/β-glucosidase from Cellulosimicrobium cellulans sp. 21 In aq. phosphate buffer at 30℃; for 0.166667h; pH=8; Enzymatic reaction;
Multi-step reaction with 2 steps
1: polyethylenimine-coated Selenomonas ruminantium β-xylosidase immobilized on glyoxyl agarose; water / aq. acetate buffer / 0.08 h / 50 °C / pH 5 / Enzymatic reaction
2: polyethylenimine-coated Selenomonas ruminantium β-xylosidase immobilized on glyoxyl agarose; water / aq. acetate buffer / 2 h / 50 °C / pH 5 / Enzymatic reaction
View Scheme
Ganoderma capense heteropolysaccharide GCPB-2, 1.03E5 Da

Ganoderma capense heteropolysaccharide GCPB-2, 1.03E5 Da

A

D-xylose
58-86-6

D-xylose

B

L-arabinose
5328-37-0

L-arabinose

Conditions
ConditionsYield
With trifluoroacetic acid In water at 120℃; for 6h; Sealed tube;
β-D-xylopyranoside

β-D-xylopyranoside

A

D-xylose
58-86-6

D-xylose

B

(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane; water at 95℃; for 1h; Inert atmosphere;A n/a
B 3.8 mg
phyllaemblicins H3

phyllaemblicins H3

A

D-xylose
58-86-6

D-xylose

B

D-glucose
50-99-7

D-glucose

Conditions
ConditionsYield
With hydrogenchloride In water at 80℃; for 6h; Sealed tube;
phyllaemblicin H10

phyllaemblicin H10

A

D-xylose
58-86-6

D-xylose

B

D-glucose
50-99-7

D-glucose

Conditions
ConditionsYield
With hydrogenchloride In water at 80℃; for 6h; Sealed tube;
β-D-Xylp-(1-4)-β-D-Xylp-(1-4)-D-Xyl
47592-59-6

β-D-Xylp-(1-4)-β-D-Xylp-(1-4)-D-Xyl

D-xylose
58-86-6

D-xylose

Conditions
ConditionsYield
With recombinant β-xylosidase/α-L-arabinofuranosidase/β-glucosidase from Cellulosimicrobium cellulans sp. 21 In aq. phosphate buffer at 30℃; for 0.166667h; pH=8; Enzymatic reaction;
Multi-step reaction with 2 steps
1: polyethylenimine-coated Selenomonas ruminantium β-xylosidase immobilized on glyoxyl agarose; water / aq. acetate buffer / 2 h / 50 °C / pH 5 / Enzymatic reaction
2: polyethylenimine-coated Selenomonas ruminantium β-xylosidase immobilized on glyoxyl agarose; water / aq. acetate buffer / 2 h / 50 °C / pH 5 / Enzymatic reaction
View Scheme
(20S,24R)-(3α,12β)-20,24-epoxy-dammara-25-hydroxyl-12-O-β-D-quinovopyranoside-3-O-β-D-xylopyranoside

(20S,24R)-(3α,12β)-20,24-epoxy-dammara-25-hydroxyl-12-O-β-D-quinovopyranoside-3-O-β-D-xylopyranoside

A

D-xylose
58-86-6

D-xylose

B

D-quionovose
7658-08-4

D-quionovose

Conditions
ConditionsYield
With hydrogenchloride In water at 100℃; for 3h;
(22R,23S,25R,26R)-spirost-5-ene-3β,23,26-triol 3-O-β-D-xylopyranosyl-(1 → 3)-β-D-glucopyranoside

(22R,23S,25R,26R)-spirost-5-ene-3β,23,26-triol 3-O-β-D-xylopyranosyl-(1 → 3)-β-D-glucopyranoside

A

D-xylose
58-86-6

D-xylose

B

D-glucose
50-99-7

D-glucose

Conditions
ConditionsYield
With hydrogenchloride In water at 90℃; for 2h;
(24R,25S)-3β-[(O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-β-D-galactopyranosyl)oxy]-24-hydroxy-5β-spirostan-12-one.

(24R,25S)-3β-[(O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-β-D-galactopyranosyl)oxy]-24-hydroxy-5β-spirostan-12-one.

A

D-xylose
58-86-6

D-xylose

B

D-glucose
50-99-7

D-glucose

C

D-Galactose
59-23-4

D-Galactose

Conditions
ConditionsYield
With hydrogenchloride; water In 1,4-dioxane at 95℃; for 2h; Inert atmosphere;
(25R)-3β-hydroxyspitost-5-en-1β-yl O-α-L-rhamnopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-β-D-xylopyranoside

(25R)-3β-hydroxyspitost-5-en-1β-yl O-α-L-rhamnopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-β-D-xylopyranoside

A

D-xylose
58-86-6

D-xylose

B

L-Rhamnose
3615-41-6

L-Rhamnose

C

(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane; water at 95℃; for 1h; Inert atmosphere;A n/a
B n/a
C 2.8 mg
beechwood xylan

beechwood xylan

D-xylose
58-86-6

D-xylose

Conditions
ConditionsYield
With Thermomyces lanuginosus xylanase; recombinant β-xylosidase/α-L-arabinofuranosidase/β-glucosidase from Cellulosimicrobium cellulans sp. 21 In aq. phosphate buffer at 37℃; for 8h; pH=8; Reagent/catalyst; Enzymatic reaction;
3-O-α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin

3-O-α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin

A

D-xylose
58-86-6

D-xylose

B

L-arabinose
5328-37-0

L-arabinose

C

L-Rhamnose
3615-41-6

L-Rhamnose

Conditions
ConditionsYield
With hydrogenchloride In water at 90℃; for 6h;
3β-O-D-xylopyranosyl-30-norolean-12,20(29)-dien-28-oic acid 28-O-β-D-glucopyranosyl ester

3β-O-D-xylopyranosyl-30-norolean-12,20(29)-dien-28-oic acid 28-O-β-D-glucopyranosyl ester

A

D-xylose
58-86-6

D-xylose

B

D-glucose
50-99-7

D-glucose

Conditions
ConditionsYield
With hydrogenchloride In water at 95℃; for 2h;
C42H64O15

C42H64O15

A

D-xylose
58-86-6

D-xylose

B

D-glucose
50-99-7

D-glucose

Conditions
ConditionsYield
With hydrogenchloride In water at 95℃; for 2h;
(20S*,24R*)-20,24-epoxy-15α,23β,25-trihydroxy-3β-(β-D-xylopyranosyloxy)-9,19-cycloart-7-en-16-one

(20S*,24R*)-20,24-epoxy-15α,23β,25-trihydroxy-3β-(β-D-xylopyranosyloxy)-9,19-cycloart-7-en-16-one

D-xylose
58-86-6

D-xylose

Conditions
ConditionsYield
With hydrogenchloride In water at 80 - 90℃; for 1h;
11-dehydro-15α-hydroxyximicidol-3-O-β-D-xylopyranoside

11-dehydro-15α-hydroxyximicidol-3-O-β-D-xylopyranoside

D-xylose
58-86-6

D-xylose

Conditions
ConditionsYield
With hydrogenchloride In water at 80 - 90℃; for 1h;
(23R,24R)-16β,23;16α,24-diepoxycycloart-7-en-3β,12β,15α,25-tetraol 3-O-β-D-xylopyranoside

(23R,24R)-16β,23;16α,24-diepoxycycloart-7-en-3β,12β,15α,25-tetraol 3-O-β-D-xylopyranoside

D-xylose
58-86-6

D-xylose

Conditions
ConditionsYield
With hydrogenchloride In water at 80 - 90℃; for 1h;
thaliside C

thaliside C

A

D-xylose
58-86-6

D-xylose

B

D-glucose
50-99-7

D-glucose

Conditions
ConditionsYield
With hydrogenchloride In water at 90℃; for 6h;
XYLITOL
87-99-0

XYLITOL

D-xylose
58-86-6

D-xylose

Conditions
ConditionsYield
With Yarrowia lipolytica short chain dehydrogenase/reductase; nicotinamide adenine dinucleotide phosphate; magnesium chloride In aq. buffer at 28℃; for 0.166667h; pH=8.0; Enzymatic reaction;
3β-[(O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-β-D-galactopyranosyl)oxy]-5β-spirost-25(27)-en-12-one

3β-[(O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-β-D-galactopyranosyl)oxy]-5β-spirost-25(27)-en-12-one

A

D-xylose
58-86-6

D-xylose

B

D-glucose
50-99-7

D-glucose

C

D-Galactose
59-23-4

D-Galactose

D

3β-hydroxy-5β-spirost-25(27)-en-12-one

3β-hydroxy-5β-spirost-25(27)-en-12-one

Conditions
ConditionsYield
With hydrogenchloride; water In 1,4-dioxane at 95℃; for 2h; Inert atmosphere;A n/a
B n/a
C n/a
D 2.9 mg
(25R)-3β-[(O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-β-D-galactopyranosyl)oxy]-5β-spirostan-12-one

(25R)-3β-[(O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-β-D-galactopyranosyl)oxy]-5β-spirostan-12-one

A

D-xylose
58-86-6

D-xylose

B

D-glucose
50-99-7

D-glucose

C

D-Galactose
59-23-4

D-Galactose

D

(25R)-3β-hydroxy-5β-spirostan-12-one
38676-82-3

(25R)-3β-hydroxy-5β-spirostan-12-one

Conditions
ConditionsYield
With hydrogenchloride; water In 1,4-dioxane at 95℃; for 2h; Inert atmosphere;A n/a
B n/a
C n/a
D 3 mg
xylohexaose
49694-21-5

xylohexaose

D-xylose
58-86-6

D-xylose

Conditions
ConditionsYield
With recombinant β-xylosidase/α-L-arabinofuranosidase/β-glucosidase from Cellulosimicrobium cellulans sp. 21 In aq. phosphate buffer at 30℃; for 0.166667h; pH=8; Enzymatic reaction;
3β-O-α-L-rhamnopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→4)]-β-D-glucopyranosyl-homo-aro-cholest-5-ene-26-O-β-D-glucopyranoside

3β-O-α-L-rhamnopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→4)]-β-D-glucopyranosyl-homo-aro-cholest-5-ene-26-O-β-D-glucopyranoside

A

D-xylose
58-86-6

D-xylose

B

L-Rhamnose
3615-41-6

L-Rhamnose

C

D-glucose
50-99-7

D-glucose

D

homo-aro-cholest-5-ene-3β,26-diol

homo-aro-cholest-5-ene-3β,26-diol

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane; water at 95℃; for 2h; Inert atmosphere;A n/a
B n/a
C n/a
D 5 mg
3-O-α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester

3-O-α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester

A

D-xylose
58-86-6

D-xylose

B

L-arabinose
5328-37-0

L-arabinose

C

L-Rhamnose
3615-41-6

L-Rhamnose

D

D-glucose
50-99-7

D-glucose

Conditions
ConditionsYield
With hydrogenchloride In water at 90℃; for 6h;
D-xylose
58-86-6

D-xylose

XYLITOL
87-99-0

XYLITOL

Conditions
ConditionsYield
With hydrogen In water at 120℃; under 15001.5 Torr; for 0.166667h; Temperature; Pressure;100%
With sodium tetrahydroborate In water at 20℃; for 3h;88%
With hydrotalcite; Pt/γ-Al2O3; hydrogen In water at 60℃; under 12001.2 Torr; for 4h; Catalytic behavior; Reagent/catalyst; Time; Green chemistry;79%
Conditions
ConditionsYield
Stage #1: methanol; D-xylose With hydrogenchloride In water for 12h;
Stage #2: With calcium carbonate In water at 20℃;
100%
With trifluoroacetic acid Ambient temperature;
With hydrogenchloride In water at 30℃; for 3.5h;
Stage #1: methanol; D-xylose With hydrogenchloride at 55℃; for 21h;
Stage #2: With silver carbonate In methanol at 25℃; for 0.5h;
D-xylose
58-86-6

D-xylose

n-Octylamine
111-86-4

n-Octylamine

C13H27NO4
67669-28-7

C13H27NO4

Conditions
ConditionsYield
In methanol at 45℃;100%
D-xylose
58-86-6

D-xylose

(S)-1-phenyl-ethylamine
2627-86-3

(S)-1-phenyl-ethylamine

C13H19NO4
1361940-04-6

C13H19NO4

Conditions
ConditionsYield
In methanol at 45℃;100%
D-xylose
58-86-6

D-xylose

(R)-1-phenyl-ethyl-amine
3886-69-9

(R)-1-phenyl-ethyl-amine

C13H19NO4
1361940-02-4

C13H19NO4

Conditions
ConditionsYield
In methanol at 45℃;100%
D-xylose
58-86-6

D-xylose

cyclohexylamine
108-91-8

cyclohexylamine

C11H21NO4
95585-48-1

C11H21NO4

Conditions
ConditionsYield
In methanol at 45℃;100%
D-xylose
58-86-6

D-xylose

N-butylamine
109-73-9

N-butylamine

N-D-Xylosyl-n-butylamin
82002-00-4

N-D-Xylosyl-n-butylamin

Conditions
ConditionsYield
In methanol at 45℃;100%
D-xylose
58-86-6

D-xylose

1-amino-2-propene
107-11-9

1-amino-2-propene

C8H15NO4
1361940-06-8

C8H15NO4

Conditions
ConditionsYield
In methanol at 45℃;100%
D-xylose
58-86-6

D-xylose

benzylamine
100-46-9

benzylamine

C12H17NO4
108942-11-6

C12H17NO4

Conditions
ConditionsYield
In methanol at 45℃;100%
D-xylose
58-86-6

D-xylose

methyl α-D-lyxopyranoside
131233-91-5

methyl α-D-lyxopyranoside

Conditions
ConditionsYield
With hydrogenchloride; methanol In water at 68℃; for 1.5h;100%
D-xylose
58-86-6

D-xylose

L-Cysteine
52-90-4

L-Cysteine

C8H14NO6S(1-)*Na(1+)

C8H14NO6S(1-)*Na(1+)

Conditions
ConditionsYield
With sodium hydroxide at 80℃; pH=9.5; Temperature; Flow reactor;100%
Conditions
ConditionsYield
With pyridine at 20℃; for 4h; Inert atmosphere;100%
D-xylose
58-86-6

D-xylose

D-Xylononitrile
52387-25-4

D-Xylononitrile

Conditions
ConditionsYield
With phenoxyamine hydrochloride In aq. phosphate buffer; water-d2 at 20℃; for 12h;98%
D-xylose
58-86-6

D-xylose

acetone
67-64-1

acetone

1,2-O-isopropylidene-α-D-xylose
20031-21-4

1,2-O-isopropylidene-α-D-xylose

Conditions
ConditionsYield
Stage #1: D-xylose; acetone With sulfuric acid
Stage #2: With hydrogenchloride In water
97%
Stage #1: D-xylose; acetone With sulfuric acid; copper(II) sulfate at 25℃;
Stage #2: With hydrogenchloride In water
D-xylose
58-86-6

D-xylose

furfural
98-01-1

furfural

Conditions
ConditionsYield
With sulfonated graphitic carbon nitride In water at 100℃; for 0.5h; Solvent; Temperature;96%
With Sulfonated graphene at 150℃; for 0.666667h; Temperature; Sealed tube;96%
With hydrogenchloride; 5-methyl-dihydro-furan-2-one In water at 224.84℃; under 28443.9 Torr; for 0.0375h; Kinetics; Temperature; Reagent/catalyst; Concentration; Flow reactor;93%
D-xylose
58-86-6

D-xylose

4,5-dimethyl-1,2-phenylenediamine
3171-45-7

4,5-dimethyl-1,2-phenylenediamine

(1'S,2'R,3'R)-5,6-dimethyl-2-[1',2',3',4'-tetrahydroxybutyl]-1H-benzimidazole

(1'S,2'R,3'R)-5,6-dimethyl-2-[1',2',3',4'-tetrahydroxybutyl]-1H-benzimidazole

Conditions
ConditionsYield
With iodine In water; acetic acid at 20℃; for 5h;96%
With iodine; acetic acid In methanol at 20℃; for 13h;
D-xylose
58-86-6

D-xylose

2-(4-chlorophenyl)-2-hydroxy-1-phenylethanone
71292-81-4

2-(4-chlorophenyl)-2-hydroxy-1-phenylethanone

(6R,7S,8S)-2-(4-chlorophenyl)-3-phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6,7,8-triol
1213264-77-7

(6R,7S,8S)-2-(4-chlorophenyl)-3-phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6,7,8-triol

Conditions
ConditionsYield
With ammonium acetate; oxalic acid at 80℃; for 0.15h; Microwave irradiation; Neat (no solvent);96%
D-xylose
58-86-6

D-xylose

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

(6R,7S,8S)-2,3-diphenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6,7,8-triol
1213264-75-5

(6R,7S,8S)-2,3-diphenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6,7,8-triol

Conditions
ConditionsYield
With ammonium acetate; oxalic acid at 80℃; for 0.183333h; Microwave irradiation; Neat (no solvent);95%
D-xylose
58-86-6

D-xylose

Trimethylenediamine
109-76-2

Trimethylenediamine

(1S,2R,3R)-1-(Hexahydro-pyrimidin-2-yl)-butane-1,2,3,4-tetraol

(1S,2R,3R)-1-(Hexahydro-pyrimidin-2-yl)-butane-1,2,3,4-tetraol

Conditions
ConditionsYield
for 48h;94%
D-xylose
58-86-6

D-xylose

(tert-Butoxycarbonylmethylene)triphenylphosphorane
86302-43-4

(tert-Butoxycarbonylmethylene)triphenylphosphorane

tert-butyl (E)-2,3-dideoxy-D-xylo-hept-2-enonate
352462-28-3

tert-butyl (E)-2,3-dideoxy-D-xylo-hept-2-enonate

Conditions
ConditionsYield
In 1,4-dioxane Wittig reaction; Heating;94%
D-xylose
58-86-6

D-xylose

phenyl isocyanate
1197040-29-1

phenyl isocyanate

4-chlorobenzamidine hydrochloride
14401-51-5

4-chlorobenzamidine hydrochloride

2-(4-chlorophenyl)-5-(hydroxymethyl)-4-phenyl-4,5,6,7-tetrahydro-3H-imidazo[4,5-b]pyridine-6,7-diol
1268853-91-3

2-(4-chlorophenyl)-5-(hydroxymethyl)-4-phenyl-4,5,6,7-tetrahydro-3H-imidazo[4,5-b]pyridine-6,7-diol

Conditions
ConditionsYield
With sodium acetate at 90℃; for 0.233333h; Ugi reaction; Microwave irradiation; neat (no solvent);94%
D-xylose
58-86-6

D-xylose

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

(1S,2R,3R)-2-(1,2,3,4-tetrahydroxybutyl)-1H-6-chlorobenzimidazole
1609208-15-2

(1S,2R,3R)-2-(1,2,3,4-tetrahydroxybutyl)-1H-6-chlorobenzimidazole

Conditions
ConditionsYield
With iodine In water; acetic acid at 20℃; for 4h;94%
D-xylose
58-86-6

D-xylose

D-ribulose 1-phosphate
7721-50-8

D-ribulose 1-phosphate

Conditions
ConditionsYield
With Thermotoga maritima MSB8 L-rhamnulose kinase; Escherichia coli D-xylose isomerase; Pseudomonas Sp, ST-24 D-tagatose 3-epimerase; ATP; sodium hydroxide pH=7.5; Enzymatic reaction;94%
With Pseudomonas Sp. St-24 D-tagatose 3-epimerase; Thermotoga maritima MSB8 L-arabinose isomerase; Thermotoga maritima MSB8 L-rhamnulose kinase; magnesium(II); manganese(II); ATP at 45℃; pH=Ca. 7.5; Enzymatic reaction;
2-phenylazlactone
1199-01-5

2-phenylazlactone

D-xylose
58-86-6

D-xylose

aniline
62-53-3

aniline

C20H20N2O5

C20H20N2O5

Conditions
ConditionsYield
With 1-butyl-3-methylimidazolium hydroxide; iodine at 20℃; for 4h; Reagent/catalyst; diastereoselective reaction;94%
D-xylose
58-86-6

D-xylose

ammonium carbamate
1111-78-0

ammonium carbamate

(2R,3R,4S,5R)-2-Amino-tetrahydro-pyran-3,4,5-triol; compound with carbamic acid

(2R,3R,4S,5R)-2-Amino-tetrahydro-pyran-3,4,5-triol; compound with carbamic acid

Conditions
ConditionsYield
With ammonium hydroxide In methanol at 37℃; for 5h;93%
D-xylose
58-86-6

D-xylose

allyl bromide
106-95-6

allyl bromide

(2R,3S,4S)-1,2,3,4,5-pentahydroxyoct-7-ene
868159-53-9

(2R,3S,4S)-1,2,3,4,5-pentahydroxyoct-7-ene

Conditions
ConditionsYield
With indium In water for 10h; Barbier reaction;93%
2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetohydrazide
1000071-56-6

2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetohydrazide

D-xylose
58-86-6

D-xylose

C12H18N4O7

C12H18N4O7

Conditions
ConditionsYield
With acetic acid In ethanol; water for 5h; Heating;93%

58-86-6Relevant articles and documents

Aqueous ionic liquids and deep eutectic solvents for cellulosic biomass pretreatment and saccharification

Xia, Shuqian,Baker, Gary A.,Li, Hao,Ravula, Sudhir,Zhao, Hua

, p. 10586 - 10596 (2014)

Ionic liquids (ILs) have proven effective solvents for pretreating lignocellulose, leading to the fast saccharification of cellulose and hemicellulose. However, the high cost of most ILs remains a major barrier to commercializing this recent approach at a practical scale. As a strategic detour, aqueous solutions of ILs are also being explored as less costly alternatives to neat ILs for cellulose pretreatment. However, limited studies on a few select IL systems are known and there remains no systematic survey of various ILs, eluding an in-depth understanding of pretreatment mechanisms afforded by aqueous IL systems. As a step toward filling this gap, this study presents results for Avicel cellulose pretreatment by neat and aqueous solutions (1.0 and 2.0 M) of 20 different ILs and three deep eutectic solvents, correlating enzymatic hydrolysis rates of pretreated cellulose with various IL properties such as hydrogen-bond basicity, polarity, Hofmeister ranking, and hydrophobicity. The pretreatment efficiencies of neat ILs may be loosely correlated to the hydrogen-bond basicity of the constituent anion and IL polarity; however, the pretreatment efficacies for aqueous ILs are more complicated and cannot be simply related to any single IL property. Several aqueous IL systems have been identified as effective alternatives to neat ILs in lignocellulose pretreatment. In particular, this study reveals that aqueous solutions of 1-butyl-3-methylimidazolium methanesulfonate ([BMIM][MeSO 3]) are effective for pretreating switchgrass (Panicum virgatum), resulting in fast saccharification of both cellulose and hemicellulose. An integrated analysis afforded by X-ray diffraction, scanning electron microscopy, thermogravimetric analysis and cellulase adsorption isotherm of lignocellulose samples is further used to deliver a more complete view of the structural changes attending aqueous IL pretreatment.

Enzymatic Hydrolysis of Black Liquor Xylan by a Novel Xylose-Tolerant, Thermostable β-Xylosidase from a Tropical Strain of Aureobasidium pullulans CBS 135684

Bankeeree, Wichanee,Akada, Rinji,Lotrakul, Pongtharin,Punnapayak, Hunsa,Prasongsuk, Sehanat

, p. 919 - 934 (2018)

From three cell-associated β-xylosidases produced by Aureobasidium pullulans CBS 135684, the principal enzyme was enriched to apparent homogeneity and found to be active at high temperatures (60–70?°C) over a pH range of 5–9 with a specific activity of 163.3?units (U) mg?1. The enzyme was thermostable, retaining over 80% of its initial activity after a 12-h incubation at 60?°C, with half-lives of 38, 22, and 10?h at 60, 65, and 70?°C, respectively. Moreover, it was tolerant to xylose inhibition with a Ki value of 18?mM. The Km and Vmax values against p-nitrophenyl-β-d-xylopyranoside were 5.57?±?0.27?mM and 137.0?±?4.8?μmol?min?1?mg?1 protein, respectively. When combining this β-xylosidase with xylanase from the same A. pullulans strain, the rate of black liquor xylan hydrolysis was significantly improved by up to 1.6-fold. The maximum xylose yield (0.812?±?0.015?g?g?1 dry weight) was obtained from a reaction mixture containing 10% (w/v) black liquor xylan, 6?U?g?1 β-xylosidase and 16?U?g?1 xylanase after incubation for 4?h at 70?°C and pH 6.0.

A new cycloartane triterpene glycoside from Souliea vaginata

Wu, Hai-Feng,Zhang, Gang,Wu, Mei-Chun,Yang, Wen-Ting,Ma, Guo-Xu,Chen, Di-Zhao,Xu, Xu-Dong,Zou, Qiong-Yu,Hu, Wei-Cheng

, p. 2316 - 2322 (2016)

A new cycloartane-type triterpene glycoside, namely soulieoside M (1), and one known compound, beesioside I (2), were isolated from the ethanolic extract of the rhizomes of Souliea vaginata. Their structures were determined spectroscopically and compared with previously reported spectral data. Compounds 1 and 2 were evaluated for their cytotoxic activities against three human cancer cell lines.

Three new cycloart-7-ene triterpenoid glycosides from Cimicifuga dahurica and their anti-inflammatory effects

Pang, Qian-Qian,Mei, Yu-Dan,Zhang, Yuan-Chu,Liu, Ling-Xian,Shi, Dan-Feng,Pan, Da-Bo,Yao, Xin-Sheng,Li, Hai-Bo,Yu, Yang

, p. 3634 - 3643 (2021)

Ten cycloart-7-ene triterpenoid glycosides, including three new compounds (1–3), were isolated from the roots of Cimicifuga dahurica. Their structures were elucidated on the basis of extensive spectroscopic analyses, chemical methods and comparison with literatures. In addition, the isolates were evaluated for their inhibitory effects on the production of NO, as well as the expressions of iNOS and COX-2 in LPS-stimulated RAW 264.7 macrophages. The results showed that compounds 3, 5, 6, 7 and 8 can reduce the release of NO in a dose-dependent manner. Mechanistically, Western blot analysis indicated that the NO inhibitory effects relied on down-regulating the expression of iNOS, and partially associated with lowering the expression of COX-2.

One new and seven known triterpene glycosides from the aerial parts of Cimicifuga dahurica

Hao, Yi-Meng,Luo, Wen,Jiang, Guan-Ze,Lv, Chong-Ning,Lu, Jin-Cai

, p. 788 - 793 (2020)

One new triterpene glycoside, asiaticoside I (1), along with seven known ones (2–8), were isolated from the aerial parts of Cimicifuga dahurica (Turcz.) Maxim. The structure of 1 was elucidated on the basis of extensive spectroscopic methods including 1D-NMR, 2D-NMR and MS data. The structures of known compounds were determined by comparison with the literature data. Compound 1 exhibited moderate cell growth inhibitory activities in vitro against HELF, non-small cell lung cancer A549, and pancreatic cancer PANC-1 cell lines, with IC50 values of 62.97, 43.19, and 60.40 μM, respectively.

Hydrothermal production of furfural from xylose and xylan as model compounds for hemicelluloses

Moeller, Maria,Schroeder, Uwe

, p. 22253 - 22260 (2013)

The uncatalyzed microwave-assisted hydrothermal conversion of xylose and xylan as hemicellulose model compounds to furfural at temperatures of 160-240 °C and reaction times of 5-240 min is investigated. With acceptable reaction rates at 200 °C the conversion of xylose provides furfural with a maximum yield of 49%. The conversion of xylan, however, requires lower temperatures (160-180 °C) in order to promote the hydrolysis of the polymer, yielding xylose as a furfural precursor. The Royal Society of Chemistry 2013.

Evasteriosides A and B and other sulfated steroids from the Pacific starfish Evasterias retifera

Levina,Kalinovskii,Andriyashchenko,Dmitrenok

, p. 2431 - 2436 (2008)

Two new polar steroidal glycosides identified as sodium (20R,22E,24R,25S)-3-O-(β-d-xylopyranosyl)-24-methyl-5α-cholest-22- ene-3β,6β,8,15α,26-pentol 26-sulfate (evasterioside A) and sodium (20R,22E)-24-O-(β-d-xylopyranosyl)-5α-cholest-22-ene-3β, 6β,8,15α,24-pentol 3-sulfate (evasterioside B) were isolated from the Pacific starfish Evasterias retifera collected in the Sea of Japan. Five known compounds, viz., coscinasterioside B, aphelasterioside A, marthasterone 3-sulfate and (20R)-cholest-7-en-3β-ol and cholesterol sulfates, were identified. The structures of the new natural compounds were established using their 2D NMR and mass spectra and some chemical transformations.

Soulieoside O, a new cyclolanostane triterpenoid glycoside from Souliea vaginata

Wu, Hai-Feng,Li, Peng-Fei,Zhu, Yin-Di,Zhang, Xiao-Po,Ma, Guo-Xu,Xu, Xu-Dong,Liu, Yi-Lin,Luo, Zheng-Hong,Chen, Di-Zhao,Zou, Qiong-Yu,Zhao, Zi-Jian

, p. 1177 - 1182 (2017)

A new cyclolanostane triterpenoid glycoside, soulieoside O (1), together with 25-O-acetylcimigenol-3-O-β-d-xylopyranoside (2) and cimigenol-3-O-β-d-xylopyranoside (3), was isolated from the rhizomes of Souliea vaginata. Their structures were characterized by spectroscopic analysis and chemical methods. The new compound showed moderate inhibitory activity against three human cancer cell lines with IC50 values of 9.3–22.5?μM.

Triterpenoids and Flavonoids from the Leaves of Astragalus membranaceus and Their Inhibitory Effects on Nitric Oxide Production

Wang, Zhi-Bin,Zhai, Ya-Dong,Ma, Zhen-Ping,Yang, Chun-Juan,Pan, Rong,Yu, Jia-Li,Wang, Qiu-Hong,Yang, Bing-You,Kuang, Hai-Xue

, p. 1575 - 1584 (2015)

Four new cycloartane triterpenes, named huangqiyegenins V and VI and huangqiyenins K and L (1-4, resp.), together with nine known triterpenoids, 5-13, and eight flavonoids, 14-21, were isolated from a 70%-EtOH extract of Astragalus membranaceus leaves. The structures of the new compounds were elucidated by detailed spectroscopic analyses, and the compounds were identified as (9β,11α,16β,20R,24S)-11,16,25-trihydroxy-20,24-epoxy-9,19-cyclolanostane-3,6-dione (1), (9β,16β,24S)-16,24,25-trihydroxy-9,19-cyclolanostane-3,6-dione (2), (3β,6α,9β,16β,20R,24R)-16,25-dihydroxy-3-(β-D-xylopyranosyloxy)-20,24-epoxy-9,19-cyclolanostan-6-yl acetate (3), and (3β,6α,9β,16β,24E)-26-(β-D-glucopyranosyloxy)-16-hydroxy-3-(β-D-xylopyranosyloxy)-9,19-cyclolanost-24-en-6-yl acetate (4). All isolated compounds were evaluated for their inhibitory activities against LPS-induced NO production in RAW264.7 macrophage cells. Compounds 1-3, 14, 15, and 18 exhibited strong inhibition on LPS-induced NO release by macrophages with IC50 values of 14.4-27.1μM.

A new triterpene and phenolic compounds from the roots of Pteroxygonum giraldii

Chai, Xin,Su, Yan-Fang,Zhang, Jun,Yan, Shi-Lun,Gao, Yan-Hong,Gao, Xiu-Mei

, p. 127 - 133 (2012)

A chemical investigation of the roots of Pteroxygonum giraldii led to the isolation of a new arborane-type triterpene, pteroxygonumnol A (1), a new myricetin glycoside, myricetin 3-O-β-D-galactopyranoside 3′-O-β-D-xylopyranoside (2), and a group of phenolic lipids, 3-6, along with four known phenolic compounds, (-)-epigallocatechin, (-)-epigallocatechin gallate, gallic acid, and 2-(4-hydroxyphenyl)acetic acid. Their structures were elucidated on the basis of extensive spectroscopic analyses. Copyright

-

Sieber

, p. 1433,1436 (1972)

-

Hudson,Harding

, p. 1038 (1917)

A New Diarylheptanoid from the Twigs of Quercus Acutissima and their Neuroprotective Activity

Cha, Joon Min,Subedi, Lalita,Khan, Zahra,Kim, Sun Yeou,Lee, Kang Ro

, p. 213 - 216 (2020)

A new diarylheptanoid glycoside, acutissioside A (4), along with five known diarylheptanoids (1–3, 5, 6) was isolated from the twigs of Quercus acutissima Carruth. The structure of the new compound was determined via spectral analysis, including NMR spectra (1H and 13C NMR, 1H–1H COSY, HSQC, HMBC) and HR-ESI-MS, acid hydrolysis, and specific optical rotation data. The neuroprotective effect of all the diarylheptanoid compounds (1–6) was evaluated. Compound 1 exhibited NGF secretion to 154.60 ± 2.87%, which was stronger than that of the positive control 6-shogaol (140.45 ± 2.18%).

Lignan glucosides from sinomenium acutum rhizomes

Kim, Ki Hyun,Moon, Sae Rom,Kim, Chung Sub,Woo, Kyeong Wan,Choi, Sang Un,Lee, Kang Ro

, p. 2144 - 2147 (2013)

The new lignan glucoside, acutumoside (1), was isolated from Sinomenium acutum rhizomes together with nine known compounds (2-10). The structure of 1 was elucidated on the basis of extensive spectroscopic analyses, including two-dimensional nuclear magnet

-

Isbell,Frush

, p. 1309,1315 (1958)

-

Comparative study on the structural characterization and α-glucosidase inhibitory activity of polysaccharide fractions extracted from Sargassum fusiforme at different pH conditions

Jia, Rui-Bo,Li, Zhao-Rong,Lin, Lianzhu,Luo, Donghui,Ou, Zhi-Rong,Zhao, Mouming,Zheng, Qianwen

, p. 602 - 610 (2021/11/30)

Sargassum fusiforme polysaccharides (SFPs), including SFP-3-40, SFP-3-60, SFP-3-80, SFP-7-40, SFP-7-60, SFP-7-80, SFP-10-40, SFP-10-60, and SFP-10-80, were extracted at different pH (3, 7, and 10), and then precipitated with graded precipitation of 40%, 60% and 80% (v/v) ethanol solution, respectively. Their physicochemical properties and α-glucosidase inhibitory activity were determined. Results showed that SFPs significantly differed in the contents of total sugar, protein, uronic acid, sulfate, the zeta potential, and molecular weight distribution. SFPs, including SFP-10-40, SFP-10-60, and SFP-10-80, had bigger absolute zeta potential value and higher respective average molecular weight in the same ethanol concentration precipitate. All samples were mainly composed of fucose, glucuronic acid, and mannose with different molar ratios. The extraction pH and precipitation ethanol solution concentration caused little changes in functional groups, but significantly altered surface morphology of SFPs. Congo red test revealed that all polysaccharides were not helical polysaccharides. Rheological measurements indicated that SFPs were pseudoplastic fluids and showed elastic behavior of the gel. Except SFP-3-40 and SFP-3-60, all other samples had a stronger α-glucosidase inhibitory activity than that of acarbose. The inhibition type of SFPs against α-glucosidase varied owing to different extraction pH and precipitation ethyl concentration. This study shows that extraction pH can significantly affect the structure and hypoglycemic activity of SFPs and provide a data support for the scientific use of Sargassum fusiforme in industrial production.

New dammarane-type glycosides from Gynostemma pentaphyllum and their lipid-lowering activity

Weng, Xin,Lou, Yun-Yun,Wang, Yun-Shan,Huang, Ya-Ping,Zhang, Jian,Yin, Zhi-Qi,Pan, Ke

, (2021/04/12)

Gynostemma pentaphyllum (Thunb.) Makino has a long history as food and diary supplement in China. At present, there are some products for hyperlipidemia in the market, including G. pentaphyllum tea, healthy wine and healthy food. In order to discover proprotein convertase subtilisin/kexin type 9 (PCSK9) inhibitors, fourteen new triterpenoid saponins named gypenoside LXXXVIII-CI (1–14) along with six known compounds (15–20) were isolated from G. pentaphyllum. Their structures were elucidated by means of various spectroscopic techniques. Eight isolates were evaluated the inhibitory effect on PCSK9 in HepG2 cells. The results showed that three dammarane-type glycosides (2, 3, 15) remarkably reduced PCSK9 expression at 10 μM concentration. These findings suggested that G. pentaphyllum was worthy of further investigation to find small molecule PCSK9 inhibitors and facilitate their utilization as functional food ingredients.

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