3688-75-3

Usage

Uses

Used in Pharmaceutical Industry:
(3R,4S,5R,6R)-2-[(2R,3S,4R,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-[[(2R,3S,4R,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxymethyl]oxane-3,4,5-triol is used as a pharmaceutical ingredient for its potential therapeutic properties. Its complex structure and multiple hydroxy groups may contribute to its bioactivity and interactions with biological systems, making it a promising candidate for the development of new drugs and therapies.
Used in Food Industry:
In the food industry, (3R,4S,5R,6R)-2-[(2R,3S,4R,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-[[(2R,3S,4R,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxymethyl]oxane-3,4,5-triol can be used as a natural sweetener or thickening agent. Its complex carbohydrate structure may provide unique taste and texture profiles, enhancing the sensory experience of food products.
Used in Cosmetics Industry:
(3R,4S,5R,6R)-2-[(2R,3S,4R,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-[[(2R,3S,4R,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxymethyl]oxane-3,4,5-triol can be utilized in the cosmetics industry as a natural moisturizing agent. Its hydrophilic properties and ability to form hydrogen bonds with water molecules may help retain moisture in the skin, providing hydration and improving skin health.
Used in Biomedical Research:
In biomedical research, (3R,4S,5R,6R)-2-[(2R,3S,4R,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-[[(2R,3S,4R,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxymethyl]oxane-3,4,5-triol can serve as a model compound for studying the structure and function of complex carbohydrates in biological systems. Its unique stereochemistry and glycosidic linkages may provide insights into carbohydrate recognition, signaling, and interactions with other biomolecules.

Synthetic route

Sucrose (57-50-1) → neokestose (3688-75-3)

Conditions	Yield
With invertase-substance from yeast
With invertase-substance from sugar beet-leaves
With invertase-substance from sheep's rumen

Sucrose (57-50-1) → α-D-fructofuranosyl-(2→1)-β-D-fructofuranosyl-(2→1)-α-D-glucopyranoside (138809-75-3) + α-D-fructofuranosyl-(2→6)-β-D-fructofuranosyl-(2→1)-α-D-glucopyranoside (138809-76-4) + α-D-fructofuranosyl-(2→6)-α-D-glucopyranosyl-(1→2)-β-D-fructofuranoside (138809-77-5) + 1-kestose (470-69-9) + neokestose (3688-75-3) + 6-kestose (562-68-5) + 6-O-α-Fructopyranosyl-D-glucose

Conditions	Yield
citric acid at 100℃; under 0.1 Torr; Product distribution; relative rates of formation;

Sucrose (57-50-1) → α-D-fructofuranose (10489-79-9) + D-fructose (470-23-5) + [βFruf(2-6)]2 + 1-kestose (470-69-9) + neokestose (3688-75-3) + 6-kestose (562-68-5)

Conditions	Yield
With potassium sulfate; potassium dihydrogenphosphate; ammonium nitrate; sodium chloride; calcium chloride In water at 32℃; for 192h; Enzymatic reaction; optical yield given as %de;

Upstream product

• 57-50-1 Sucrose 

Relevant academic research and scientific papers

NMR structural study of fructans produced by Bacillus sp. 3B6, bacterium isolated in cloud water

Bacillus sp. 3B6, bacterium isolated from cloud water, was incubated on sucrose for exopolysaccharide production. Dialysis of the obtained mixture (MWCO 500) afforded dialyzate (DIM) and retentate (RIM). Both were separated by size exclusion chromatography. RIM afforded eight fractions: levan exopolysaccharide (EPS), fructooligosaccharides (FOSs) of levan and inulin types with different degrees of polymerization (dp 2-7) and monosaccharides fructose:glucose = 9:1. Levan was composed of two components with molecular mass ～3500 and ～100 kDa in the ratio 2.3:1. Disaccharide fraction contained difructose anhydride DFA IV. 1-Kestose, 6-kestose, and neokestose were identified as trisaccharides in the ratio 2:1:3. Fractions with dp 4-7 were mixtures of FOSs of levan (2,6-βFruf) and inulin (1,2-βFruf) type. DIM separation afforded two dominant fractions: monosaccharides with fructose: glucose ratio 1:3; disaccharide fraction contained sucrose only. DIM trisaccharide fraction contained 1-kestose, 6-kestose, and neokestose in the ratio1.5:1:2, penta and hexasaccharide fractions contained FOSs of levan type (2,6-βFruf) containing α-glucose. In the pentasaccharide fraction also the presence of a homopentasaccharide composed of 2,6-linked βFruf units only was identified. Nystose, inulin (1,2-βFruf) type, was identified as DIM tetrasaccharide. Identification of levan 2,6-βFruf and inulin 1,2-βFruf type oligosaccharides in the incubation medium suggests both levansucrase and inulosucrase enzymes activity in Bacillus sp. 3B6.

Formation of trisaccharides (kestoses) by pyrolysis of sucrose

Amorphous sucrose, containing citric acid as catalyst, undergoes thermolysis at 100° to yield fructofuranosyl cation and D-glucose. The cation reacts with unchanged sucrose to form all three of the known kestoses, and also their α-fructofuranosyl anomers. Two of the latter are resistant to invertase hydrolysis. A new fructosylglucose disaccharide is also formed. Amorphous sucrose, containing citric acid as catalyst, undergoes thermolysis at 100° to yield fructofuranosyl cation and D-glucose. The cation reacts with unchanged sucrose to form all three of the known kestoses, and also their α-fructofuranosyl anomers. Two of the latter are resistant to invertase hydrolysis. A new fructosylglucose disaccharide is also formed.