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2595-97-3

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2595-97-3 Usage

Chemical Properties

white crystalline powder

Uses

D-Allose is a rare naturally occurring monosaccharide, is known to exert anti-proliferative effects on cancer cells. The effects of D-Allose on the cellular membranes of hormone-refractory prostate ca ncer cell line (DU145), hormone-sensitive prostate cancer cell line (LNCaP), and normal prostate epithelial cells (PrEC) were studied at the molecular level by phospholipid profiling using a shotgun l ipidomic method.

Definition

ChEBI: The D-enantiomer of allopyranose.

Check Digit Verification of cas no

The CAS Registry Mumber 2595-97-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,5,9 and 5 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 2595-97:
(6*2)+(5*5)+(4*9)+(3*5)+(2*9)+(1*7)=113
113 % 10 = 3
So 2595-97-3 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-/m1/s1

2595-97-3 Well-known Company Product Price

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  • Alfa Aesar

  • (A16810)  beta-D-Allose, 98%   

  • 2595-97-3

  • 100mg

  • 615.0CNY

  • Detail
  • Alfa Aesar

  • (A16810)  beta-D-Allose, 98%   

  • 2595-97-3

  • 500mg

  • 2538.0CNY

  • Detail

2595-97-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name aldehydo-D-allose

1.2 Other means of identification

Product number -
Other names D-Allose

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Processing Aids and Additives
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:2595-97-3 SDS

2595-97-3Synthetic route

2-aminopyridine
504-29-0

2-aminopyridine

D-psicose
551-68-8

D-psicose

A

D-altrose
1990-29-0

D-altrose

B

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
Stage #1: D-psicose With 2-aminopyridine; acetic acid at 90℃; Lobry de Bruyn-van Ekenstein transformation; Sealed tube;
Stage #2: 2-aminopyridine With acetic acid at 90℃; Sealed tube;
Stage #3: With trifluoroacetic acid at 65℃; for 1h;
A 11%
B 32%
D-altrose
1990-29-0

D-altrose

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
With molybdic acid In water for 0.05h; Bilik reaction; microwave irradiation;24%
D-psicose
551-68-8

D-psicose

A

D-altrose
1990-29-0

D-altrose

B

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
With potassium hydroxide In water at 25℃; for 336h; Product distribution; Kinetics;
D-altrose
1990-29-0

D-altrose

A

D-psicose
551-68-8

D-psicose

B

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
With potassium hydroxide In water at 25℃; for 336h; Product distribution; Kinetics;
1-Deoxy-1-nitro-D-allitol
120019-25-2

1-Deoxy-1-nitro-D-allitol

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
With sulfuric acid0.12 g
Cardiomanol
127324-55-4

Cardiomanol

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
With trifluoroacetic acid at 100℃; for 1h;25 mg
N-{1-[(3aR,4R,6R,6aR)-6-((R)-1,2-Dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-acetamide
79974-65-5

N-{1-[(3aR,4R,6R,6aR)-6-((R)-1,2-Dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-acetamide

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
With Dowex 50 resin (H+) In water at 100℃; for 1.5h;
chrysoeriol 7-(2''-O-β-D-allopyranosyl)-β-D-glucopyranoside

chrysoeriol 7-(2''-O-β-D-allopyranosyl)-β-D-glucopyranoside

A

D-glucose
50-99-7

D-glucose

B

D-Allose
2595-97-3

D-Allose

C

chrysoeriol
491-71-4

chrysoeriol

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 100℃; for 1h;
p-hydroxyphenyl β-D-alloside

p-hydroxyphenyl β-D-alloside

A

D-Allose
2595-97-3

D-Allose

B

hydroquinone
123-31-9

hydroquinone

Conditions
ConditionsYield
With hydrogenchloride for 2h; Heating;A n/a
B 13 mg
D-allono-1,4-lactone
29474-78-0

D-allono-1,4-lactone

sodium amalgam

sodium amalgam

D-Allose
2595-97-3

D-Allose

D-allonic acid-4-lactone

D-allonic acid-4-lactone

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
With sodium amalgam; water; oxalic acid Reagens 4: Natriumoxalat;
d-allonic acid lactone

d-allonic acid lactone

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
With sodium amalgam
D-gluconic acid
21675-42-3

D-gluconic acid

sodium amalgam

sodium amalgam

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
das Lacton reagiert;
(2R,3R,4R)-2,3,4-Tris-benzyloxy-4-[(R)-2-(4-methoxy-phenyl)-[1,3]dioxolan-4-yl]-butyraldehyde

(2R,3R,4R)-2,3,4-Tris-benzyloxy-4-[(R)-2-(4-methoxy-phenyl)-[1,3]dioxolan-4-yl]-butyraldehyde

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In tetrahydrofuran; water
D-Fructose
57-48-7

D-Fructose

A

D-Mannose
3458-28-4

D-Mannose

B

D-glucose
50-99-7

D-glucose

C

D-altrose
1990-29-0

D-altrose

D

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
With 4-methylmorpholine N-oxide at 110℃; Product distribution;
D-glucose
50-99-7

D-glucose

A

D-Mannose
3458-28-4

D-Mannose

B

D-Galactose
59-23-4

D-Galactose

C

D-altrose
1990-29-0

D-altrose

D

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
With 4-methylmorpholine N-oxide at 110℃; Product distribution;
(23E)-5β,19-epoxycucurbita-6,23,25-trien-3β-ol 3-O-β-D-allopyranoside

(23E)-5β,19-epoxycucurbita-6,23,25-trien-3β-ol 3-O-β-D-allopyranoside

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
With hydrogenchloride In methanol for 1h; Heating;
(23S)-5β,19-epoxy-23-methoxycucurbita-6,24-dien-3β-ol 3-O-β-D-allopyranoside

(23S)-5β,19-epoxy-23-methoxycucurbita-6,24-dien-3β-ol 3-O-β-D-allopyranoside

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
With hydrogenchloride In methanol for 1h; Heating;
(19R,23R)-5β,19-epoxy-19,23-dimethoxycucurbita-6,24-dien-3β-ol 3-O-β-D-allopyranoside

(19R,23R)-5β,19-epoxy-19,23-dimethoxycucurbita-6,24-dien-3β-ol 3-O-β-D-allopyranoside

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
With hydrogenchloride In methanol for 1h; Heating;
D-ribose
50-69-1

D-ribose

bromine water

bromine water

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 0.2 g / Na / methanol / 1.5 h
2: 0.12 g / 2N H2SO4
View Scheme
4-N-acetyl-1-(2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,5-furanosyl)cytosine
63064-67-5

4-N-acetyl-1-(2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,5-furanosyl)cytosine

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 38 percent / tetrahydrofuran / 2 h / 60 °C
2: 28 percent / boron trifluoride-ether / tetrahydrofuran / 0.08 h / Ambient temperature
3: Dowex 50 resin (H+) / H2O / 1.5 h / 100 °C
View Scheme
N-[1-((3aR,4R,6R,6aR)-2,2-Dimethyl-6-oxiranyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-acetamide
79974-63-3, 79974-64-4

N-[1-((3aR,4R,6R,6aR)-2,2-Dimethyl-6-oxiranyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-acetamide

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 28 percent / boron trifluoride-ether / tetrahydrofuran / 0.08 h / Ambient temperature
2: Dowex 50 resin (H+) / H2O / 1.5 h / 100 °C
View Scheme
4-N-acetyl-1-<5-deoxy-2,3-O-isopropylidene-5,5-(N,N'-diphenylethylenediamino)-β-D-ribofuranosyl>cytosine
79974-62-2

4-N-acetyl-1-<5-deoxy-2,3-O-isopropylidene-5,5-(N,N'-diphenylethylenediamino)-β-D-ribofuranosyl>cytosine

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Dowex 50 resin (H+) / trifluoroacetic acid; H2O / 1 h / Ambient temperature
2: 38 percent / tetrahydrofuran / 2 h / 60 °C
3: 28 percent / boron trifluoride-ether / tetrahydrofuran / 0.08 h / Ambient temperature
4: Dowex 50 resin (H+) / H2O / 1.5 h / 100 °C
View Scheme
2',3'-O-isopropylidene-N4-acetylcytidine
16667-80-4

2',3'-O-isopropylidene-N4-acetylcytidine

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1.) dicyclohexylcarbodi-imide, pyridine, trifluoroacetic acid, 2.) AcOH / 1.) DMSO, H2O, RT, 30 min, 2.) MeOH, 1 h
2: Dowex 50 resin (H+) / trifluoroacetic acid; H2O / 1 h / Ambient temperature
3: 38 percent / tetrahydrofuran / 2 h / 60 °C
4: 28 percent / boron trifluoride-ether / tetrahydrofuran / 0.08 h / Ambient temperature
5: Dowex 50 resin (H+) / H2O / 1.5 h / 100 °C
View Scheme
25-hydroxy-7β-methoxycucurbita-5,23(E)-dien-19-al 3-O-β-D-allopyranoside
1310536-12-9

25-hydroxy-7β-methoxycucurbita-5,23(E)-dien-19-al 3-O-β-D-allopyranoside

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
With hydrogenchloride; water In 1,4-dioxane at 80℃; for 3h;
(23R)-7β,23-dihydroxycucurbita-5,24-dien-19-al 3-O-β-D-allopyranoside
1310536-13-0

(23R)-7β,23-dihydroxycucurbita-5,24-dien-19-al 3-O-β-D-allopyranoside

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
With hydrogenchloride; water In 1,4-dioxane at 80℃; for 3h;
(1R,4S,5S,8R,9R,12S,13S,16S)-8-[(2R,4E)-6-methoxy-6-methylhept-4-en-2-yl]-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.01,13.04,12.05,9]nonadec-2-en-19-one 16-O-β-D-allopyranoside
1310536-14-1

(1R,4S,5S,8R,9R,12S,13S,16S)-8-[(2R,4E)-6-methoxy-6-methylhept-4-en-2-yl]-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.01,13.04,12.05,9]nonadec-2-en-19-one 16-O-β-D-allopyranoside

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
With hydrogenchloride; water In 1,4-dioxane at 80℃; for 3h;
D-Allose
2595-97-3

D-Allose

3-amino-2-phenylquinazolin-4(3H)-one
1904-60-5

3-amino-2-phenylquinazolin-4(3H)-one

2-phenyl-3-{(1Z)-(2,3,4,5,6-pentahydroxyhexylidene)amino}quinazolin-4(3H)-one

2-phenyl-3-{(1Z)-(2,3,4,5,6-pentahydroxyhexylidene)amino}quinazolin-4(3H)-one

Conditions
ConditionsYield
With NaY zeolite catalyst for 0.316667h; Microwave irradiation; Neat (no solvent);85%
indole
120-72-9

indole

D-Allose
2595-97-3

D-Allose

acetic anhydride
108-24-7

acetic anhydride

Acetic acid (1S,2S,3R,4R)-2,3,4,5-tetraacetoxy-1-[bis-(1H-indol-2-yl)-methyl]-pentyl ester

Acetic acid (1S,2S,3R,4R)-2,3,4,5-tetraacetoxy-1-[bis-(1H-indol-2-yl)-methyl]-pentyl ester

Conditions
ConditionsYield
Stage #1: indole; D-Allose; scandium tris(trifluoromethanesulfonate) In ethanol; water at 50℃; for 48h;
Stage #2: acetic anhydride With pyridine; dmap at 20℃;
82%
D-Allose
2595-97-3

D-Allose

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

2,2-dimethoxy-propane

2,3:5,6-Di-O-isopropylidene-α-D-allofuranose
27108-13-0

2,3:5,6-Di-O-isopropylidene-α-D-allofuranose

Conditions
ConditionsYield
With calcium sulfate; toluene-4-sulfonic acid In 1,2-dimethoxyethane at 20℃; for 24h; Condensation;71%
D-Allose
2595-97-3

D-Allose

D-allose (Z)-oxime

D-allose (Z)-oxime

Conditions
ConditionsYield
Stage #1: With hydroxylamine hydrochloride; sodium methylate In ethanol at 20℃;
Stage #2: D-Allose In ethanol at 70℃;
68%
D-Allose
2595-97-3

D-Allose

N-Phenyl-N'-thiobenzoyl-hydrazin
13437-75-7

N-Phenyl-N'-thiobenzoyl-hydrazin

(1R,2R,3R,4R)-1-<(2S)-(3,5-diphenyl-2,3-dihydro-<1,3,4>thiadiazol-2-yl)>-pentane-1,2,3,4,5-pentaol

(1R,2R,3R,4R)-1-<(2S)-(3,5-diphenyl-2,3-dihydro-<1,3,4>thiadiazol-2-yl)>-pentane-1,2,3,4,5-pentaol

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 20℃; for 20h;66%
D-Allose
2595-97-3

D-Allose

D-allonitrile

D-allonitrile

Conditions
ConditionsYield
With phenoxyamine hydrochloride In aq. phosphate buffer; water-d2 at 20℃; for 48h;63%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

D-Allose
2595-97-3

D-Allose

A

3,6-anhydro-2-deoxy-D-glycero-D-altro-octono-1,4-lactone
315202-37-0

3,6-anhydro-2-deoxy-D-glycero-D-altro-octono-1,4-lactone

B

3,6-anhydro-2-deoxy-D-glycero-D-gluco-octono-1,4-lactone
315202-38-1

3,6-anhydro-2-deoxy-D-glycero-D-gluco-octono-1,4-lactone

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 48 - 49℃; for 240h; Substitution; cyclization;A 20%
B 61%
With tert-butylamine In N,N-dimethyl-formamide at 40℃; for 120h; Substitution; cyclization;A 31%
B 51%
D-Allose
2595-97-3

D-Allose

S,S'-((4-(2-aminoethoxy)-1,2-phenylene)bis(methylene)) bis(2-methylpropanethioate) hydrochloride

S,S'-((4-(2-aminoethoxy)-1,2-phenylene)bis(methylene)) bis(2-methylpropanethioate) hydrochloride

S,S'-((4-(2-(bis((2S,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexyl)amino)ethoxy)-1,2-phenylene)bis(methylene)) bis(2-methylpropanethioate) hydrochloride

S,S'-((4-(2-(bis((2S,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexyl)amino)ethoxy)-1,2-phenylene)bis(methylene)) bis(2-methylpropanethioate) hydrochloride

Conditions
ConditionsYield
Stage #1: D-Allose; S,S'-((4-(2-aminoethoxy)-1,2-phenylene)bis(methylene)) bis(2-methylpropanethioate) hydrochloride With sodium cyanoborohydride; acetic acid In methanol at 55℃; for 7h;
Stage #2: With hydrogenchloride In water pH=3;
56%
D-Allose
2595-97-3

D-Allose

5-hydroxymethyl-2-furfuraldehyde
67-47-0

5-hydroxymethyl-2-furfuraldehyde

Conditions
ConditionsYield
With chromium dichloride at 120℃; for 3h; Reagent/catalyst; Inert atmosphere; Ionic liquid;44%
D-Allose
2595-97-3

D-Allose

D-altrose
1990-29-0

D-altrose

Conditions
ConditionsYield
With molybdic acid In water for 0.05h; Bilik reaction; microwave irradiation;42%
nitromethane
75-52-5

nitromethane

D-Allose
2595-97-3

D-Allose

A

1-deoxy-1-nitro-D-glycero-D-galacto-heptitol
130930-34-6

1-deoxy-1-nitro-D-glycero-D-galacto-heptitol

B

1-Deoxy-1-nitro-D-glycero-D-alloheptitol
130930-33-5

1-Deoxy-1-nitro-D-glycero-D-alloheptitol

Conditions
ConditionsYield
With sodium methylate In methanol; dimethyl sulfoxide for 24h;A 30%
B 21%
D-Allose
2595-97-3

D-Allose

(3S)-O-(N-methoxyglycyl)betulinic acid
1101863-07-3

(3S)-O-(N-methoxyglycyl)betulinic acid

(3S)-O-(N-methoxy-N-β-D-allosylglycyl)betulinic acid
1101863-11-9

(3S)-O-(N-methoxy-N-β-D-allosylglycyl)betulinic acid

Conditions
ConditionsYield
In methanol; dichloromethane at 40℃; for 48h;23%
D-Allose
2595-97-3

D-Allose

A

D-altronic acid
22430-69-9

D-altronic acid

B

D-gluconic acid
21675-42-3

D-gluconic acid

Conditions
ConditionsYield
With sodium anthraquinone-2-sulfonate; calcium chloride In sodium hydroxide at 50℃;A 4%
B 13%
D-Allose
2595-97-3

D-Allose

2,4-diacetylphloroglucinol
2161-86-6

2,4-diacetylphloroglucinol

C16H20O10
1044237-24-2

C16H20O10

Conditions
ConditionsYield
With scandium tris(trifluoromethanesulfonate) In ethanol; water for 66h; Heating;6.25%
Conditions
ConditionsYield
With water anschliessend Erhitzen der Reaktionsloesung unter vermindertem Druck;
D-Allose
2595-97-3

D-Allose

allitol
488-44-8

allitol

Conditions
ConditionsYield
With Ni-doped silica; ethanol at 100 - 140℃; under 66195.7 - 88260.9 Torr; Hydrogenation;
With sodium tetrahydroborate at 4℃; for 2h;
With sodium tetrahydroborate
With sodium tetrahydroborate In water for 1h;
D-Allose
2595-97-3

D-Allose

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
With pyridine
D-Allose
2595-97-3

D-Allose

1,6-anhydro-β-D-glucopyranoside
14059-68-8

1,6-anhydro-β-D-glucopyranoside

Conditions
ConditionsYield
With hydrogenchloride
D-Allose
2595-97-3

D-Allose

acetic anhydride
108-24-7

acetic anhydride

β-D-allose pentaacetate
4257-94-7

β-D-allose pentaacetate

Conditions
ConditionsYield
With sodium acetate
D-Allose
2595-97-3

D-Allose

phenylhydrazine
100-63-0

phenylhydrazine

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

lyxo-[2]Hexosulose-bis-phenylhydrazon

Conditions
ConditionsYield
With acetic acid phenyl-d-altrosazone;
D-Allose
2595-97-3

D-Allose

2,2,2-trifluoro-N-methyl-N-(2,2,2-trifluoroacetyl)acetamide
685-27-8

2,2,2-trifluoro-N-methyl-N-(2,2,2-trifluoroacetyl)acetamide

N-benzyloxyamine
622-33-3

N-benzyloxyamine

A

trifluoroacetylated allose anti-O-benzyloxime
128613-60-5

trifluoroacetylated allose anti-O-benzyloxime

B

trifluoroacetylated allose syn-O-benzyloxime
128613-78-5

trifluoroacetylated allose syn-O-benzyloxime

Conditions
ConditionsYield
1.) NMP, 75 deg C, 30 min, 2.) NMP, RT, 5-10 min; Multistep reaction;
D-Allose
2595-97-3

D-Allose

A

D-psicose
551-68-8

D-psicose

B

D-altrose
1990-29-0

D-altrose

Conditions
ConditionsYield
With potassium hydroxide In water at 25℃; for 336h; Product distribution; Kinetics;
D-Allose
2595-97-3

D-Allose

D-gluconic acid
21675-42-3

D-gluconic acid

Conditions
ConditionsYield
With potassium hydroxide; platinum on activated charcoal In water at 25℃; under 760 Torr; for 3h; Rate constant; Mechanism; relative, initial rate;
D-Allose
2595-97-3

D-Allose

D-psicose 1-phosphate
126-25-0, 26001-54-7, 52050-05-2

D-psicose 1-phosphate

Conditions
ConditionsYield
With ATP 1) L-rhamnose isomerase, tris buffer pH 8.0, mercaptoethanol, MgCl2, ATP (cat.), 2) L-rhamnulose kinase, PEP/pyruvate kinase; Yield given. Multistep reaction;

2595-97-3Relevant articles and documents

New 3,4-seco-diterpene and coumarin derivative from the leaves of Trigonostemon flavidus Gagnep

Ban, Ninh Khac,Linh, Tran My,Mai, Nguyen Chi,Tai, Bui Huu,Nhiem, Nguyen Xuan,Hoang, Nguyen Huy,Kiem, Phan Van

, p. 3247 - 3254 (2022)

Two new compounds named trigoflavidus A (1) and trigoflavidus B (2), and eight known compounds, trigoflavidone (3), heterophypene (4), howpene C (5), 3,4-seco-sonderianol (6), trigonochinene C (7), fraxidin (8), isofraxidin (9), and isofraxetin (10) were isolated from the leaves of Trigonostemon flavidus Gagnep. by various chromatographic methods. Their chemical structures were elucidated via UV, IR, HR-ESI-MS and NMR spectroscopic methods and divided into two groups including six 3,4-seco-diterpenes (1, 3-7) and four coumarins (2, 8-10). Absolute configurations at stereocenters of compound 1 were confirmed by comparison of its CD spectra with those of the TD-DFT calculations. At a concentration of 30 μM, compounds 1–10 exhibited weak cytotoxic activity toward LU1, HepG2, MCF7, and SKMel2 human cell lines (cell viability all over 50%).

Cucurbitane-type triterpene glycosides from the fruits of Momordica charantia

Kim, Young Ho,Nhiem, Nguyen Xuan,Kiem, Phan Van,Minh, Chau Van,Ban, Ninh Khac,Cuong, Nguyen Xuan,Ha, Le Minh,Tai, Bui Huu,Quang, Tran Hong,Tung, Nguyen Huu

, p. 392 - 396 (2010)

The chemical study of Momordica charantia fruits led to the isolation of three new cucurbitane triterpene glycosides, momordicosides U, V, and W (1-3). The structures of these compounds were determined to be (19R,23R)-5β, 19-epoxy-19-methoxycucurbita-6,24-diene-3β, 23-diol 3-O-β-D- allopyranoside (1), (23R)-5β, 19-epoxycucurbita-6,24-diene-3β, 23-diol 3-O-β-D-allopyranoside (2), and (19R)-5β, 19-epoxy-19,25- dihydroxycucurbita-6,23(E)-diene-3β-ol 3-O-β-D-glucopyranoside (3), by chemical and spectroscopic methods.

Acute and sub-chronic toxicity of D-allose in rats

Iga, Yusuke,Nakamichi, Kazunori,Shirai, Yoko,Matsuo, Tatsuhiro

, p. 1476 - 1478 (2010)

We examined the acute and sub-chronic toxicity of D-allose in rats. In the acute toxicity test, the calculated LD50 value was 20.5 g/kg. In the sub-chronic toxicity test, no difference was found among the four groups in most of the serum chemical and hematological test results. These results suggest that D-allose is not toxic to rats.

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Pratt,Richtmyer

, p. 1906 (1955)

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Phenolic glycosides from the Chinese liverwort reboulia hemisphaerica

Wang, Li-Ning,Guo, Dong-Xiao,Wang, Shu-Qi,Wu, Chang-Sheng,Rehman, Mujeeb Ur,Lou, Hong-Xiang

, p. 1146 - 1152 (2011)

Four new phenolic glycosides, named rebouosides A-D (1-4, resp.), along with three known ones 2-(3,4-dihydroxyphenyl)ethyl 2-O-α-L- rhamnopyranosyl-β-D-allopyranoside (5), 2-(3,4-dihydroxyphenyl)ethyl β-D-allopyranoside (6), 2-(3,4-dihydroxyphenyl)ethyl β-D- glucopyranoside (7), and a nucleoside, inosine (8), were isolated from Chinese liverwort Reboulia hemisphaerica. Their structures were elucidated by acidic hydrolysis and extensive spectroscopic methods, including 2D-NMR techniques.

HPLC-ESIMSn profiling, isolation, structural elucidation, and evaluation of the antioxidant potential of phenolics from Paepalanthus geniculatus

Pereira Do Amaral, Fabiano,Napolitano, Assunta,Masullo, Milena,Campaner Dos Santos, Lourdes,Festa, Michela,Vilegas, Wagner,Pizza, Cosimo,Piacente, Sonia

, p. 547 - 556 (2012)

The methanol extract of the flowers of Paepalanthus geniculatus Kunth. showed radical-scavenging activity in the TEAC assay. An analytical approach based on HPLC-ESIMSn was applied to obtain the metabolite profile of this extract and led to the rapid identification of 19 polyphenolic compounds comprising flavonoids and naphthopyranones. The new naphthopyranone (10, 16), quercetagetin (1, 5, 7, 13), and galetine derivatives (9, 11, 17, 19), and a flavonol glucoside cyclodimer in the truxillate form (12), were identified. Compounds 2, 6, and 7 showed the highest antioxidant capacity and ability to affect the levels of intracellular ROS in human prostate cancer cells (PC3).

α-Glucosidase inhibition properties of cucurbitane-type triterpene glycosides from the fruits of Momordica charantia

Nhiem, Nguyen Xuan,Kiem, Phan Van,Minh, Chau Van,Ban, Ninh Khac,Cuong, Nguyen Xuan,Tung, Nguyen Huu,Ha, Le Minh,Ha, Do Thi,Tai, Bui Huu,Quang, Tran Hong,Ngoc, Tran Minh,Kwon, Young-In,Jang, Hae-Dong,Kim, Young Ho

, p. 720 - 724 (2010)

Fourteen cucurbitane-type triterpene glycosides (1-14) were isolated from a methanol extract of Momordica charantia fruits, including three new compounds, charantosides A-C (1, 5, 6). Their structures were elucidated by chemical and spectroscopic methods. All isolated compounds were evaluated for α-glucosidase inhibitory effect. Of which, 12 and 13 showed moderate inhibitory activity against α-glucosidase. Whereas, 2, 3, 6-11, and 14 showed weak inhibitory activity, and 1, 4, and 5 were inactive.

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.

Method for preparing lactic acid through catalytically converting carbohydrate

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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.

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