4-O-beta-D-Galactopyranosyl-D-fructofuranose

Base Information

• Chemical Name: 4-O-beta-D-Galactopyranosyl-D-fructofuranose
• CAS No.: 4618-18-2
• Molecular Formula: C12H22O11
• Molecular Weight: 342.3
• Hs Code.: 29400090
• UNII: 9U7D5QH5AE
• Nikkaji Number: J208.671I
• Mol file: 4618-18-2.mol

Synonyms:(3S,4R,5R)-1,3,5,6-TETRAHYDROXY-4-{[(2S,3R,4S,5R,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL]OXY}HEXAN-2-ONE;Lactulose (Enulose);MFCD00151469;LACTULOSE [INN];LACTULOSE [JAN];LACTULOSE [MI];LACTULOSE [INCI];LACTULOSE [USAN];LACTULOSE [VANDF];LACTULOSE [MART.];LACTULOSE [WHO-DD];LACTULOSE JP17 [JAN];SCHEMBL1980980;LACTULOSE [EP IMPURITY];LACTULOSE [ORANGE BOOK];LACTULOSE [EP MONOGRAPH];LACTULOSE [USP IMPURITY];HY-B1172;s1511;BCP9000833;CCG-267946;CS-4778;D-Fructose, 4-O-b-D-galactopyranosyl-;NCGC00386418-01;F81537;4-O-.BETA.-D-GALACTOPYRANOSYL-D-FRUCTOFURANOSE;(3S,4R,5R)-1,3,5,6-tetrahydroxy-4-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexan-2-one;(3S,4R,5R)-1,3,5,6-tetrahydroxy-4-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)hexan-2-one

Chemical Property of 4-O-beta-D-Galactopyranosyl-D-fructofuranose

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 2.43E-28mmHg at 25°C
• Melting Point: ~169 °C (dec.)
• Refractive Index: 1,45-1,47
• Boiling Point: 680.5 °C at 760 mmHg
• PKA: 11.67±0.20(Predicted)
• Flash Point: 365.4 °C
• PSA: 197.37000
• Density: 1.77 g/cm³
• LogP: -5.55300
• Storage Temp.: Refrigerator
• Solubility.: Freely soluble in water, sparingly soluble in methanol, practically insoluble in toluene.
• Water Solubility.: 76.4 G/100 ML (30 ºC)
• XLogP3: -4.8
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 8
• Exact Mass: 342.11621151
• Heavy Atom Count: 23
• Complexity: 378

Purity/Quality:

98%, ^*data from raw suppliers

Lactulose ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C1C(C(C(C(O1)OC(C(CO)O)C(C(=O)CO)O)O)O)O)O
• Isomeric SMILES: C([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]([C@@H](CO)O)[C@@H](C(=O)CO)O)O)O)O)O
• Uses: Lactulose is is a synthetic, non-digestible sugar used in the treatment of chronic constipation; laxative. pharmaceutical excipient A keto analogue of lactose.
• Indications: Osmotic laxatives (e.g., lactulose, sorbitol) are poorly absorbed or nonabsorbable compounds that draw additional fluid into the GI tract. Lumen osmolality increases, and fluid movement occurs secondary to osmotic pressure. Lactulose is a synthetic disaccharide that is poorly absorbed from the GI tract, since no mammalian enzyme is capable of hydrolyzing it to its monosaccharide components. It therefore reaches the colon unchanged and is metabolized by colonic bacteria to lactic acid and to small quantities of formic and acetic acids.
• Clinical Use: Lactulose is used in the treatment of hepatic encephalopathy.

Technology Process of 4-O-beta-D-Galactopyranosyl-D-fructofuranose

There total 4 articles about 4-O-beta-D-Galactopyranosyl-D-fructofuranose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

LACTOSE (5965-66-2) → D-tagatose (87-81-0,18875-34-8) + D-glucose (50-99-7) + D-Galactose (59-23-4) + lactulose (4618-18-2,576-08-9)

Guidance literature:

With Zeolite Na-X; water; at 85 ℃; for 10h; Product distribution; var. reag.: var. minerals and zeolites; var. pH, isomerization;

DOI:10.1016/S0008-6215(00)90699-2

Reference yield:

D-(+)-lactose (63-42-3) → lactulose (4618-18-2,576-08-9)

Guidance literature:

With calcium hydroxide; water;

DOI:10.1021/ja01368a060

Reference yield:

D-Fructose (57-48-7,18875-34-8) + D-(+)-lactose (63-42-3) → lactulose (4618-18-2,576-08-9)

Guidance literature:

With β-galactosidase from Aspergillus oryzae; at 40 ℃; pH=4.5; aq. buffer; Enzymatic reaction;

DOI:10.1016/j.molcatb.2011.06.007

upstream raw materials:

D-(+)-lactose

LACTOSE

O⁴-β-D-galactopyranosyl-1-p-toluidino-1-deoxy-D-fructose

D-Fructose

Downstream raw materials:

β-D-galactopyranosyl-(1→?4)-β-D-fructofuranosyl-(2→?1)-α-D-glucopyranoside

leucrose

D-Fructose

D-Galactose

Refernces

• 1、 Guerrero, Cecilia,Vera, Carlos,Plou, Francisco,Illanes, Andres. "Influence of reaction conditions on the selectivity of the synthesis of lactulose with microbial β-galactosidases". . p. 206 - 212. Retrieved 2011.
• 2、 Song, Yoon-Seok,Lee, Hee-Uk,Park, Chulhwan,Kim, Seung-Wook. "Optimization of lactulose synthesis from whey lactose by immobilized β-galactosidase and glucose isomerase". . p. 1 - 5. Retrieved 2013/05/09.