[ CAS No. 499-40-1 ] {[proInfo.proName]}

Name: 499-40-1|(2R,3S,4R,5R)-2,3,4,5-Tetrahydroxy-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexanal|97%
Brand: Ambeed
SKU: A709101
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2D 3D

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Quality Control of [ 499-40-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 499-40-1 ]

SDS Specification

Alternatived Products of [ 499-40-1 ]

Product Details of [ 499-40-1 ]

CAS No. :	499-40-1	MDL No. :	MFCD00065373
Formula :	C₁₂H₂₂O₁₁	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	342.30	Pubchem ID :	-
Synonyms :	6-O-α-D-Glucopyranosyl-D-glucose;D-Isomaltose	Chemical Name :	(2R,3S,4R,5R)-2,3,4,5-Tetrahydroxy-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexanal

Calculated chemistry of [ 499-40-1 ]

Physicochemical Properties

Num. heavy atoms :	23
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.92
Num. rotatable bonds :	8
Num. H-bond acceptors :	11.0
Num. H-bond donors :	8.0
Molar Refractivity :	69.35
TPSA :	197.37 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-12.38 cm/s

Lipophilicity

Log Po/w (iLOGP) :	-0.43
Log Po/w (XLOGP3) :	-5.62
Log Po/w (WLOGP) :	-5.55
Log Po/w (MLOGP) :	-4.92
Log Po/w (SILICOS-IT) :	-3.29
Consensus Log Po/w :	-3.96

Druglikeness

Lipinski :	2.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	4.0
Bioavailability Score :	0.17

Water Solubility

Log S (ESOL) :	2.11
Solubility :	43700.0 mg/ml ; 128.0 mol/l
Class :	Highly soluble
Log S (Ali) :	2.14
Solubility :	46800.0 mg/ml ; 137.0 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	4.08
Solubility :	4150000.0 mg/ml ; 12100.0 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	5.17

Safety of [ 499-40-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 499-40-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 499-40-1 ]
Downstream synthetic route of [ 499-40-1 ]

[ 499-40-1 ] Synthesis Path-Upstream 1~2

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Reference： [1] Journal of Agricultural and Food Chemistry, 2011, vol. 59, # 8, p. 4148 - 4155

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Reference： [1] Journal of Agricultural and Food Chemistry, 2011, vol. 59, # 8, p. 4148 - 4155

[ 499-40-1 ] Synthesis Path-Downstream 1~33

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Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 2503
[2]Biochemical Journal,1954,vol. 58,p. 396,397, 400

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Reference： [1]Journal of the Chemical Society,1953,p. 3588,3591

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Reference： [1]Analytical Chemistry,1955,vol. 27,p. 396,397

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Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 1062
[2]Journal of Organic Chemistry,1995,vol. 60,p. 8245 - 8256

Yield	Reaction Conditions	Operation in experiment
		As evident from the results in Table 38, it was revealed that the addition of isoamylase increases the yield of isomaltose.

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Reference： [1]Journal of Organic Chemistry,1995,vol. 60,p. 8245 - 8256

Yield	Reaction Conditions	Operation in experiment
85%		The high isomaltose content syrup thus obtained was hydrogenated in accordance with the method in Experiment 36, followed by removing the Raney Nickel catalyst from the mixture. The resulting mixture was decolored with an activated charcoal, desalted for purification with ion-exchange resins in H- and OH-forms, concentrated, and dried in vacuo to obtain a high isomaltitol content powder in a yield of about 85%.

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Yield	Reaction Conditions	Operation in experiment
	With hydrogen;nickel; In water; at 20 - 130℃; under 22502.3 Torr;Autoclave;Product distribution / selectivity;	Hydrogenation of isomaltulose/trehalulose solution, 30% dry matter, 30 barTable 5746 g aqueous isomaltulose/trehalulose solution (30% dry matter) of the composition shown in Table 5 (quantification according to the method explained for Examples 1-4) was introduced into the autoclave reactor. At a temperature of 300C the solution was supplemented with 2.2 g, 9.0 g and 15.7 g of nickel catalyst (Degussa, BK 111 W), respectively, corresponding to 1%, 4% and 7% of catalyst, respectively, based on the dry sugar content of the isomaltulose/trehalulose solution. The reactor was closed and inertized 3 times with nitrogen. The nitrogen was exchanged with hydrogen 3 times and subsequently, the hydrogen pressure was adjusted to 30 bar. The rotation speed was increased to 1,220 rpm and the isomaltulose/trehalose mixture was heated from 300C to 1300C with a heating rate of 3C/min. Consumed hydrogen was automatically replenished so that the pressure of 30 bar was maintained throughout the course of the hydrogenation reaction. Samples were taken when the temperature of 1300C was reached having the compositions set out in Table 6 (quantification according to the method explained for Examples 1-3).Table 6 <n="16"/>It is evident from Table 6 that the GPM/GPS ratio is dependant on the catalyst concentration at constant heating rate. The ratio cis/trans isomer (GPM/GPS) decreases with increased catalyst concentration.The reaction containing 1% catalyst was continued for an additional hour at 13O0C in order to demonstrate that the reaction can be completed and the remaining isomaltulose content can be reduced below 0.05% without changing the obtained GPM/GPS ratio significantly.; Example 11Hydrogenation of isomaltulose/trehalulose solution, 30% dry matter, 30 bar746 g aqueous isomaltulose/trehalulose solution (30% dry matter) of a composition shown in Table 6 (, see Example 5; quantification according to the method explained for Examples 1-4), introduced into the autoclave reactor described above, was supplemented with 9.0 g nickel catalyst (Degussa, BK 111 W), corresponding to 4% of catalyst based on the dry matter content of the isomaltulose/trehalulose solution. The reactor was closed and inertized twice with nitrogen. The nitrogen was exchanged with hydrogen twice and subsequently, the hydrogen pressure was adjusted to 30 bar while mixing at 333 rpm. The rotation speed was increased to 1,220 rpm and the isomaltulose/ trehalulose solution was heated from about 2O0C to 1300C with various heating rates, respectively. Consumed hydrogen was automatically replenished so that the pressure of 30 bar was maintained during the course of the hydrogenation reaction. Samples were taken when the temperature of 1300C was reached, having the compositions set out in Table 14 (quantification according to the method explained for Examples 1-3). <n="23"/>Table 14It is evident from Table 14 that the GPM/GPS ratio is dependant on the heating rate of the reaction mixture.

Reference： [1]Patent: WO2008/77640,2008,A1 .Location in patent: Page/Page column 14-15; 21-22

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Yield	Reaction Conditions	Operation in experiment
	With hydrogen;nickel; In water; at 20 - 130℃; under 22502.3 - 97509.8 Torr;Autoclave;Product distribution / selectivity;	Hydrogenation of isomaltulose solution, 50% dry matter, 30 bar816 g aqueous isomaltulose solution (50% dry matter) was introduced into the autoclave reactor. At a temperature of 300C, the solution was supplemented with 4.1 g, 16.3 g and 28.6 g of nickel catalyst (Degussa, BK 111 W), respectively, corresponding to 1%, 4% and 7% of catalyst, respectively, based on the dry sugar content of the isomaltulose solution. The reactor was closed and inertized 3 times with nitrogen. The nitrogen was exchanged with hydrogen 3 times and subsequently, the hydrogen pressure was adjusted to 30 bar. The rotation speed was increased to 1,220 rpm and the isomaltulose solution was heated from 300C to 1300C with a heating rate of 3C/min. Consumed hydrogen was automatically replenished so that the pressure of 30 bar was maintained throughout the course of the hydrogenation reaction. Samples were taken when the temperature of 1300C was reached, having the compositions set out in Table 2.Table 2GPS*: GPS consists primarily of 1,6-GPS and minor amounts of 1,1-GPS, the latter being formed from trehalulose. 1,1-GPS and 1,6-GPS co-elute in the HPLC method used.It is evident from Table 2 that the GPM/GPS ratio is dependant on the catalyst concentration at constant heating rate. The ratio cis/trans isomer (GPM/GPS) decreases with increased catalyst concentrationThe reaction containing 1% catalyst was continued for an additional hour at 1300C in order to demonstrate that the reaction can be completed and the remaining <n="13"/>isomaltulose content can be reduced below 0.05% without changing the obtained GPM/GPS ratio significantly.; Example 2 Hydrogenation of isomaltulose solution, 50% dry matter, 130 bar816 g aqueous isomaltulose solution (50% dry matter) was introduced into the autoclave reactor. At a temperature of 300C the solution was supplemented with 4.1 g, 16.3 g and 28.6 g of nickel catalyst (Degussa, BK 111 W), respectively, corresponding to 1%, 4% and 7% of catalyst, respectively, based on the dry sugar content of the isomaltulose solution. The reactor was closed and inertized 3 times with nitrogen. The nitrogen was exchanged with hydrogen 3 times and subsequently, the hydrogen pressure was adjusted to 130 bar. The rotation speed was increased to 1,220 rpm and the isomaltulose solution was heated from 300C to 13O0C with a heating rate of 3C/min. Consumed hydrogen was automatically replenished so that the pressure of 130 bar was maintained throughout the course of the hydrogenation reaction. Samples were taken when the temperature of 1300C was reached, having the compositions set out in Table 3.Table 3It is evident from Table 3 that the GPM/GPS ratio is dependant on the catalyst concentration at constant heating rate. The ratio cis/trans isomer (GPM/GPS) decreases with increased catalyst concentration.; Example 3Hydrogenation of isomaltulose solution, 30% dry matter, 80 bar746 g aqueous isomaltulose solution (30% dry matter) was introduced into the autoclave reactor. At a temperature of 3O0C the solution was supplemented with 2.2 g, 9.0 g and 15.7 g of nickel catalyst (Degussa, BK 111 W), respectively, corresponding to 1%, 4% and 7% of catalyst, respectively, based on the dry sugar content of the isomaltulose solution. The reactor was closed an inertized 3 times with nitrogen. The nitrogen was exchanged with hydrogen 3 times and subsequently, the hydrogen pressure was adjusted to 80 bar. The rotation speed was increased to 1,220 rpm and the isomaltulose solution was heated from 300C to 1300C with a heating rate of 3C/min. Consumed hydrogen was automatically replenished so that the pressure of 80 bar was maintained throughout the course of the hydrogenation reaction. The samples were taken when the temperature of 1300C was reached, having the compositions set out in table 4.Table 4It is evident from table 4 that the GPM/GPS ratio is dependent on the catalyst concentration at constant heating rate. The ratio cis/trans isomer (GPM/GPS) decreases with increased catalyst concentration.; Examples 6-8The following embodiments of the present invention relate to a process for the preparation of a mixture of the stereoisomeric sugar alcohols 6-O-alpha-D- glucopyranosyl-D-sorbitol (1,6-GPS) and 1-O-alpha-D-glucopyranosyl-D-mannitol (1,1- GPM) by hydrogenation of isomaltulose using a Raney nickel catalyst at increased hydrogen pressure, wherein the ratio of 1,6-GPS/1,1-GPM can be regulated by changing the heating rate of the reaction mixture. The isomaltulose reagent is specified in Table 1 (supra). The isomaltulose was hydrogenated as described for Examples 1-3 with different starting temperatures as mentioned in the following examples. For analysis of the obtained hydrogenation product samples, the same procedures were utilized as stated above. <n="18"/>Example 6Hydrogenation of isomaltulose solution, 30% dry matter, 30 bar746 g aqueous isomaltulose solution (30% dry matter), introduced into the autoclave reactor, was supplemented with 9...

Reference： [1]Patent: WO2008/77640,2008,A1 .Location in patent: Page/Page column 10-13; 16-20

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Reference： [1]Chemistry of Natural Compounds,2008,vol. 44,p. 749 - 751

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Yield	Reaction Conditions	Operation in experiment
	In water; at 40℃;pH 6.0;Acetate buffer; Enzymatic reaction;Reactivity;	Experiment 12-1Product from Maltose by the Enzyme ReactionAqueous maltose solution and acetate buffer (pH 6.0) were mixed to give final concentrations of 1percent (w/v) and 10 mM, respectively, to make into a substrate solution. The substrate solution was admixed with 10 units/g-solid substrate of alpha-glucosyltransferase, obtained by the method in Experiment 6, and followed by the enzyme reaction at 40° C. and pH 6.0. Aliquots were sampled from the reaction mixture with time and the reaction was stopped by keeping at 100° C. for 10 min. The saccharide compositions of the samples were measured by HPLC and GC. HPLC and GC were carried out under the conditions described in Experiment 4-2. The results are in Table 10. TABLE 10 Reaction Saccharide Composition (percent, w/w) Time DP1 DP2 DP3 (hr) Glucose Maltose Isomaltose Neotrehalose Maltotriose Panose Isopanose Isomaltotriose DP4 DP5 DP6 0 0.0 99.2 0.0 0.0 0.8 0.0 0.0 0.0 0.0 0.0 0.0 1 12.1 55.0 0.7 0.0 13.2 16.1 0.0 0.0 2.9 0.0 0.0 2 18.4 33.5 1.0 0.0 14.4 24.1 0.0 0.0 7.6 1.0 0.0 4 23.7 17.3 2.5 0.0 10.0 29.3 0.0 0.0 13.0 4.2 0.0 8 27.0 10.4 4.7 0.0 4.9 27.8 0.0 0.0 15.9 5.3 4.0 24 30.4 6.0 10.0 2.6 1.4 11.0 1.0 3.6 15.3 10.2 8.5 48 31.5 6.2 13.8 3.9 0.7 4.1 1.5 4.2 12.4 10.3 11.4 DP: Glucose polymerization degreeAs is evident from the results in Table 10, at initial stage (after one hour) of the reaction, glucose, maltotriose, and panose were formed as major reaction products from the substrate, maltose, by the action of the alpha-glucosyltransferase of the present invention. Also, oligosaccharides with a glucose polymerization degree of 4 and 5 were formed when the reaction time was elapsed 2 to 4 hours. Accompanying with the progress of the reaction, the content of maltotriose reached a maximum, 14.4percent, at 2 hours and then decreased; and the content of panose reached a maximum, 29.3percent at 4 hours and then decreased; and the content of isomaltose was increased with the decrease of the contents of maltotriose and panose. Further, the contents of isomaltose and oligosaccharides with a glucose polymerization degree of 4 or higher were increased until 48 hours.From these results, it was revealed that the alpha-glucosyltransferase of the present invention acts on maltose and forms glucose, maltotriose, and panose by catalyzing both alpha-1,4 and alpha-1,6 glucosyl transfer at initial stage of the reaction; and forms isomaltose, which is formed by alpha-1,6 glucosyl transfer to glucose, and isopanose and isomaltotriose, which are formed by alpha-1,4 and alpha-1,6 glucosyl transfer to isomaltose accompanied with the progress of the reaction. Since the identification of many kinds of oligosaccharide with glucose polymerization degree of 4 or higher is difficult in this experiment, the reaction mechanism of the enzyme was investigated in the following Experiment 12-2 using maltopentaose, whose glucose polymerization degree is higher than maltose, as substrate.

Reference： [1]Patent: US2010/120710,2010,A1 .Location in patent: Page/Page column 18-19

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Reference： [1]Journal of Agricultural and Food Chemistry,2010,vol. 58,p. 4819 - 4824

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β-Glcp-(1->4)-[α-Glcp-(1->6)]-Glcp [ No CAS ]

Reference： [1]Biochimie,2010,vol. 92,p. 1818 - 1826

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Reference： [1]Biochemical and Biophysical Research Communications,2010,vol. 397,p. 87 - 92

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Reference： [1]Biochemical and Biophysical Research Communications,2010,vol. 397,p. 87 - 92

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6(I)-α-glucosylpanose [ No CAS ]
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[ 499-40-1 ]