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551-68-8 Usage

Chemical Properties

Clear colorless to yellow liquid or powder

Uses

D-Psicose is a C3 epimer of L-Fructose, which maintains the ability to reduce fat accumulation when added to a diet through inhibition of intestinal α-glucosidase.

Definition

ChEBI: The D-enantiomer of psicose.

Enzyme inhibitor

This ketohexose (FW = 180.16 g/mol), also known as D-ribo-2-hexulose and reportedly fpound in cane molasses, has epimers of D-psicose are Dfructose, D-sorbose, and L-tagatose. D-Psicose is an alternative substrate for fructokinase. The structural composition of D-psicose at 27°C in D2O is 22% a-pyranose, 24% b-pyranose, 39% a-furanose, and 15% bfuranose. Target(s): ketohexokinase, or hepatic fructokinase; also alternative substrate.

Check Digit Verification of cas no

The CAS Registry Mumber 551-68-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 1 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 551-68:
(5*5)+(4*5)+(3*1)+(2*6)+(1*8)=68
68 % 10 = 8
So 551-68-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3,5-9,11-12H,1-2H2/t3-,5-,6+/m1/s1

551-68-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name D-psicose

1.2 Other means of identification

Product number -
Other names D-PSICOSE

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:551-68-8 SDS

551-68-8Synthetic route

(S)-4-((R)-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)(hydroxy)methyl)-2,2-dimethyl-1,3-dioxan-5-one
915947-48-7

(S)-4-((R)-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)(hydroxy)methyl)-2,2-dimethyl-1,3-dioxan-5-one

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
With Dowex 50W-X2-200 In water100%
D-Fructose
57-48-7

D-Fructose

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
With immobilized D-psicose epimerase from Corynebacterium glutamicum KCCM 11046 In water at 30 - 50℃; Enzymatic reaction;75%
With triethylamine In ethanol for 15h; Heating; Yield given;
With D-tagatose 3-epimerase at 25℃; Enzymatic reaction;
D-Glucose
2280-44-6

D-Glucose

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

A

D-psicose
551-68-8

D-psicose

B

D-Sorbose
3615-56-3

D-Sorbose

Conditions
ConditionsYield
With recombinant Escherichia coli strain RhuA-Y; isopropyl β-D-thiogalactopyranoside for 20h; Enzymatic reaction; Overall yield = 35.6 %; Overall yield = 960 mg; diastereoselective reaction;A 10.4%
B 10.6%
With recombinant Escherichia coli strain FucA-Y; isopropyl β-D-thiogalactopyranoside for 20h; Enzymatic reaction; Overall yield = 35.6 %; Overall yield = 960 mg; diastereoselective reaction;A n/a
B n/a
D-glucose
50-99-7

D-glucose

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
With ammonium hydroxide
D-Allose
2595-97-3

D-Allose

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
With pyridine
Penta-O-acetyl-keto-D-psicose
98574-01-7

Penta-O-acetyl-keto-D-psicose

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
With barium dihydroxide; water
O1,O2-isopropylidene-O3-methanesulfonyl-β-D-fructopyranose

O1,O2-isopropylidene-O3-methanesulfonyl-β-D-fructopyranose

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
With sulfuric acid Behandeln des (mit Hilfe von Bariumcarbonat) von Sulfat-Ionen befreiten Reaktionsgemisches mit wss.Natronlauge;
D-Mannose
3458-28-4

D-Mannose

A

glycolic Acid
79-14-1

glycolic Acid

B

LACTIC ACID
849585-22-4

LACTIC ACID

C

D-Fructose
57-48-7

D-Fructose

D

D-psicose
551-68-8

D-psicose

E

D-glucose
50-99-7

D-glucose

F

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
With potassium hydroxide In water at 78℃; for 0.333333h; Rate constant; Product distribution; Mechanism; isomerization equilibrium; degradation to acids; varying time, OH(1-) concentration 0.001 M to O.1 M; also in presence of Ca(2+) up to 0.06 M;
D-glucose
50-99-7

D-glucose

A

glycolic Acid
79-14-1

glycolic Acid

B

LACTIC ACID
849585-22-4

LACTIC ACID

C

D-Fructose
57-48-7

D-Fructose

D

D-Mannose
3458-28-4

D-Mannose

E

D-psicose
551-68-8

D-psicose

F

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
With potassium hydroxide In water at 78℃; for 0.333333h; Rate constant; Product distribution; Mechanism; isomerization equilibrium; degradation to acids; varying time, OH(1-) concentration 0.001 M to O.1 M; also in presence of Ca(2+) up to 0.06 M;
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;
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;
3.4.5.6-Tetra-O-acetyl-D-psicose
97833-77-7, 121351-05-1

3.4.5.6-Tetra-O-acetyl-D-psicose

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
With barium dihydroxide Yield given;
sulfuric acid
7664-93-9

sulfuric acid

O1,O2-isopropylidene-O3-methanesulfonyl-β-D-fructopyranose

O1,O2-isopropylidene-O3-methanesulfonyl-β-D-fructopyranose

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
Behandeln des von Sulfat befreiten Reaktionsgemisches mit wss. Natronlauge;
D-Fructose
57-48-7

D-Fructose

water
7732-18-5

water

D-psicose
551-68-8

D-psicose

D-Fructose
57-48-7

D-Fructose

aqueous lead (II)-hydroxide

aqueous lead (II)-hydroxide

D-psicose
551-68-8

D-psicose

D-Fructose
57-48-7

D-Fructose

water
7732-18-5

water

A

D-Mannose
3458-28-4

D-Mannose

B

D-psicose
551-68-8

D-psicose

C

D-glucose
50-99-7

D-glucose

Conditions
ConditionsYield
Behandeln mit einem basischen Anionenaustauscher;
Behandeln mit einem basischen Anionenaustauscher, zeitlicher Verlauf dieser Reaktion;
D-Fructose
57-48-7

D-Fructose

aqueous calcium hydroxide

aqueous calcium hydroxide

A

LACTIC ACID
849585-22-4

LACTIC ACID

B

D-psicose
551-68-8

D-psicose

C

D-glucose
50-99-7

D-glucose

D

2-methyl-D-ribonic acid

2-methyl-D-ribonic acid

Conditions
ConditionsYield
at 25℃; zeitlicher Verlauf unter Ausschluss von Sauerstoff;
D-glucose
50-99-7

D-glucose

water
7732-18-5

water

A

D-Fructose
57-48-7

D-Fructose

B

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
Beim Erwaermen einer gepufferten Loesung vom pH 7.5;
D-glucose
50-99-7

D-glucose

ammonium hydroxide

ammonium hydroxide

A

D-Fructose
57-48-7

D-Fructose

B

D-Mannose
3458-28-4

D-Mannose

C

D-psicose
551-68-8

D-psicose

D-glucose
50-99-7

D-glucose

aqueous calcium hydroxide (0.04n)

aqueous calcium hydroxide (0.04n)

A

D-Fructose
57-48-7

D-Fructose

B

D-Mannose
3458-28-4

D-Mannose

C

D-psicose
551-68-8

D-psicose

D

2-methyl-D-ribonic acid

2-methyl-D-ribonic acid

Conditions
ConditionsYield
at 25℃; Zeitlicher Verlauf; unter Ausschluss von Sauerstoff; Produkt 5: DL-Milchsaeure;
D-Fructose
57-48-7

D-Fructose

A

D-Mannose
3458-28-4

D-Mannose

B

D-psicose
551-68-8

D-psicose

C

D-glucose
50-99-7

D-glucose

Conditions
ConditionsYield
With sodium hydroxide In water at 80℃; for 2h; pH=8.3; Kinetics; Lobry de Brujn-Alberda van Ekenstein reaction;A n/a
B 6.46 % Chromat.
C n/a
Stage #1: D-Fructose With aluminum oxide In pyridine for 9h; Heating;
Stage #2: With sulfuric acid In acetone for 2h; Further stages.;
A 13 % Chromat.
B 10 % Chromat.
C 22 % Chromat.
D-glucose
50-99-7

D-glucose

A

D-Fructose
57-48-7

D-Fructose

B

D-Mannose
3458-28-4

D-Mannose

C

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
With sodium hydroxide In water at 80℃; for 2h; pH=8.3; Kinetics; Lobry de Brujn-Alberda van Ekenstein reaction;A n/a
B n/a
C 3.28 % Chromat.
D-Mannose
3458-28-4

D-Mannose

A

D-Fructose
57-48-7

D-Fructose

B

D-psicose
551-68-8

D-psicose

C

D-glucose
50-99-7

D-glucose

D

D-arabino-[3]hexulose
53989-88-1

D-arabino-[3]hexulose

Conditions
ConditionsYield
With sodium aluminate In water at 35℃; for 20h; Product distribution; Further Variations:; reaction times;
D-Allose
2595-97-3

D-Allose

A

D-Fructose
57-48-7

D-Fructose

B

D-psicose
551-68-8

D-psicose

C

D-altrose
1990-29-0

D-altrose

Conditions
ConditionsYield
Stage #1: D-Allose With aluminum oxide In pyridine for 2h; Heating;
Stage #2: With sulfuric acid In acetone for 2h; Further stages.;
A 2 % Chromat.
B 50 % Chromat.
C 2 % Chromat.
2,3,4,5-tetra-O-acetyl-aldehydo-D-ribose
30571-54-1

2,3,4,5-tetra-O-acetyl-aldehydo-D-ribose

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / 3-ethylbenzothiazolium bromide / ethanol / 72 h / 70 °C
2: barium hydroxide
View Scheme
tetra-O-acetyl-D-ribonic acid
61212-28-0

tetra-O-acetyl-D-ribonic acid

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: diethyl ether; PCl5
2: diethyl ether
3: copper (II)-acetate
4: barium hydroxide; water
View Scheme
tetra-O-acetyl-D-ribonic acid chloride
18968-65-5

tetra-O-acetyl-D-ribonic acid chloride

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: diethyl ether
2: copper (II)-acetate
3: barium hydroxide; water
View Scheme
tetra-O-acetyl-1-diazo-keto-D-1-deoxy-psicose
6632-53-7

tetra-O-acetyl-1-diazo-keto-D-1-deoxy-psicose

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: copper (II)-acetate
2: barium hydroxide; water
View Scheme
D-psicose
551-68-8

D-psicose

acetone
67-64-1

acetone

1,2:3,4-di-O-isopropylidene-β-D-psicofuranose
34626-95-4

1,2:3,4-di-O-isopropylidene-β-D-psicofuranose

Conditions
ConditionsYield
With hydrogenchloride; copper(II) sulfate In water at 20℃;73%
With sulfuric acid for 2h; Ambient temperature;
D-psicose
551-68-8

D-psicose

sodium cyanide
143-33-9

sodium cyanide

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

acetone
67-64-1

acetone

A

2,2':5,6-di-O-isopropylidene-2-C-hydroxymethyl-D-altrono-1,4-lactone

2,2':5,6-di-O-isopropylidene-2-C-hydroxymethyl-D-altrono-1,4-lactone

B

6-O-tert-butyldimethylsilyl-2-C-tert-butyldimethylsilyloxymethyl-2,3-O-isopropylidene-L-allono-1,4-lactone

6-O-tert-butyldimethylsilyl-2-C-tert-butyldimethylsilyloxymethyl-2,3-O-isopropylidene-L-allono-1,4-lactone

Conditions
ConditionsYield
Multistep reaction;A 19%
B 71%
D-psicose
551-68-8

D-psicose

benzoyl chloride
98-88-4

benzoyl chloride

A

C34H28O10
1232836-56-4

C34H28O10

B

C34H28O10
1232836-55-3

C34H28O10

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 3h;A 12%
B 54%
D-psicose
551-68-8

D-psicose

sodium cyanide
143-33-9

sodium cyanide

acetone
67-64-1

acetone

A

2,2':5,6-di-O-isopropylidene-2-C-hydroxymethyl-D-altrono-1,4-lactone

2,2':5,6-di-O-isopropylidene-2-C-hydroxymethyl-D-altrono-1,4-lactone

B

2,3:5,6-di-O-isopropylidene-2-C-hydroxymethyl-D-allono-1,4-lactone
864846-18-4

2,3:5,6-di-O-isopropylidene-2-C-hydroxymethyl-D-allono-1,4-lactone

Conditions
ConditionsYield
Stage #1: D-psicose; sodium cyanide With water Kiliani reaction; Heating;
Stage #2: With Amberlite IR-120 H(1+); water at 20℃;
Stage #3: acetone With copper(I) sulfate; sulfuric acid; copper(II) sulfate
A n/a
B 38%
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-psicose
551-68-8

D-psicose

1,2:3,4-di-O-isopropylidene-D-psicofuranose
29474-80-4

1,2:3,4-di-O-isopropylidene-D-psicofuranose

Conditions
ConditionsYield
With sulfuric acid; copper(II) sulfate; acetone
D-psicose
551-68-8

D-psicose

phenylhydrazine
100-63-0

phenylhydrazine

D-allose osazone
6164-71-2

D-allose osazone

Conditions
ConditionsYield
With sodium hydrogensulfite; acetic acid
D-psicose
551-68-8

D-psicose

dimethyl sulfate
77-78-1

dimethyl sulfate

methyl-[tetra-O-methyl-psicofuranoside
23259-20-3, 94942-15-1

methyl-[tetra-O-methyl-psicofuranoside

Conditions
ConditionsYield
With sodium hydroxide (+)-methyl-O-methyl-ξ-D-psicofuranoside>;
D-psicose
551-68-8

D-psicose

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

trifluoroacetylated psicose-O-benzyloxime

trifluoroacetylated psicose-O-benzyloxime

Conditions
ConditionsYield
1.) NMP, 75 deg C, 30 min, 2.) NMP, RT, 3 h; Multistep reaction;
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-psicose
551-68-8

D-psicose

A

glycolic Acid
79-14-1

glycolic Acid

B

LACTIC ACID
849585-22-4

LACTIC ACID

C

D-Fructose
57-48-7

D-Fructose

D

D-Mannose
3458-28-4

D-Mannose

E

D-glucose
50-99-7

D-glucose

F

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
With potassium hydroxide In water at 78℃; for 0.333333h; Rate constant; Product distribution; Mechanism; isomerization equilibrium; degradation to acids; varying time, OH(1-) concentration 0.001 M to O.1 M; also in presence of Ca(2+) up to 0.06 M;
O-Methylhydroxylamin
67-62-9

O-Methylhydroxylamin

D-psicose
551-68-8

D-psicose

1-(Trimethylsilyl)imidazole
18156-74-6

1-(Trimethylsilyl)imidazole

trimethylsilyl ether of psicose O-methyloxime
56196-14-6, 128705-57-7, 128705-81-7, 129445-30-3, 129445-32-5

trimethylsilyl ether of psicose O-methyloxime

Conditions
ConditionsYield
1.) NMP, 75 deg C, 30 min, 2.) NMP, RT, 5-10 min; Multistep reaction;
D-psicose
551-68-8

D-psicose

N-benzyloxyamine
622-33-3

N-benzyloxyamine

1-(Trimethylsilyl)imidazole
18156-74-6

1-(Trimethylsilyl)imidazole

trimethylsilyl ether of psicose-O-benzyloxime

trimethylsilyl ether of psicose-O-benzyloxime

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

551-68-8Relevant articles and documents

Few-Unit-Cell MFI Zeolite Synthesized using a Simple Di-quaternary Ammonium Structure-Directing Agent

Abeykoon, Milinda,Al-Thabaiti, Shaeel,Bell, Alexis T.,Boscoboinik, J. Anibal,Dai, Heng,Dauenhauer, Paul,Dorneles de Mello, Matheus,Duan, Xuekui,Ghosh, Supriya,Kamaluddin, Huda Sharbini,Khan, Zaheer,Kumar, Gaurav,Li, Xinyu,Lu, Peng,Luo, Tianyi,Mkhoyan, K. Andre,Narasimharao, Katabathini,Qi, Liang,Rimer, Jeffrey D.,Tsapatsis, Michael

supporting information, p. 19214 - 19221 (2021/08/09)

Synthesis of a pentasil-type zeolite with ultra-small few-unit-cell crystalline domains, which we call FDP (few-unit-cell crystalline domain pentasil), is reported. FDP is made using bis-1,5(tributyl ammonium) pentamethylene cations as structure directing agent (SDA). This di-quaternary ammonium SDA combines butyl ammonium, in place of the one commonly used for MFI synthesis, propyl ammonium, and a five-carbon nitrogen-connecting chain, in place of the six-carbon connecting chain SDAs that are known to fit well within the MFI pores. X-ray diffraction analysis and electron microscopy imaging of FDP indicate ca. 10 nm crystalline domains organized in hierarchical micro-/meso-porous aggregates exhibiting mesoscopic order with an aggregate particle size up to ca. 5 μm. Al and Sn can be incorporated into the FDP zeolite framework to produce active and selective methanol-to-hydrocarbon and glucose isomerization catalysts, respectively.

Characterization of alditol oxidase from Streptomyces coelicolor and its application in the production of rare sugars

Chen, Zhou,Gao, Xiao-Dong,Li, Fen,Li, Zijie,Wang, Ning

, (2020/04/10)

A synthetic platform for the cascade synthesis of rare sugars using Escherichia coli whole cells was established. In the cascade, the donor substrate dihydroxyacetone phosphate (DHAP) was generated from glycerol by glycerol kinase (GK) and glycerol phosphate oxidase (GPO). The acceptor D-glyceraldehyde was directly produced from glycerol by an alditol oxidase. Then, the aldol reaction between DHAP and D-glyceraldehyde was performed by L-rhamnulose-1-phosphate aldolase (RhaD) to generate the corresponding sugar-1-phosphate. Finally, the phosphate group was removed by fructose-1-phosphatase (YqaB) to obtain the rare sugars D-sorbose and D-psicose. To accomplish this goal, the alditol oxidase from Streptomyces coelicolor (AldOS.coe) was expressed in E. coli and the purified AldOS.coe was characterized. Furthermore, a recombinant E. coli strain overexpressing six enzymes including AldOS.coe was constructed. Under the optimized conditions, it produced 7.9 g/L of D-sorbose and D-psicose with a total conversion rate of 17.7% from glycerol. This study provides a useful and cost-effective method for the synthesis of rare sugars.

ENZYMATIC PRODUCTION OF D-ALLULOSE

-

, (2020/07/16)

The current disclosure provides a process for enzymatically converting a saccharide into allulose. The invention also relates to a process for preparing allulose where the process involves converting fructose 6-phosphate (F6P) to allulose 6-phosphate (A6P), catalyzed by allulose 6-phosphate 3-epimerase (A6PE), and converting the A6P to allulose, catalyzed by allulose 6-phosphate phosphatase (A6PP).

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