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Chemical Structure| 50-70-4
Chemical Structure| 50-70-4
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Product Details of [ 50-70-4 ]

CAS No. :50-70-4 MDL No. :MFCD00004708
Formula : C6H14O6 Boiling Point : -
Linear Structure Formula :- InChI Key :FBPFZTCFMRRESA-JGWLITMVSA-N
M.W :182.17 Pubchem ID :5780
Synonyms :
D-Sorbitol

Calculated chemistry of [ 50-70-4 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 5
Num. H-bond acceptors : 6.0
Num. H-bond donors : 6.0
Molar Refractivity : 37.93
TPSA : 121.38 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -9.61 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.88
Log Po/w (XLOGP3) : -3.1
Log Po/w (WLOGP) : -3.59
Log Po/w (MLOGP) : -2.77
Log Po/w (SILICOS-IT) : -1.91
Consensus Log Po/w : -1.9

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 3.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 1.31
Solubility : 3750.0 mg/ml ; 20.6 mol/l
Class : Highly soluble
Log S (Ali) : 1.12
Solubility : 2380.0 mg/ml ; 13.1 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 2.57
Solubility : 67100.0 mg/ml ; 368.0 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.3

Safety of [ 50-70-4 ]

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

Application In Synthesis of [ 50-70-4 ]

* 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 [ 50-70-4 ]

[ 50-70-4 ] Synthesis Path-Upstream   1~14

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Reference: [1] Patent: US2010/311973, 2010, A1, . Location in patent: Page/Page column 11
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  • [ 109-07-9 ]
  • [ 107-15-3 ]
  • [ 78-90-0 ]
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  • [ 106-55-8 ]
Reference: [1] Patent: US2010/311973, 2010, A1, . Location in patent: Page/Page column 10
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  • [ 641-74-7 ]
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Reference: [1] ChemSusChem, 2017, vol. 10, # 1, p. 53 - 57
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Reference: [1] ChemSusChem, 2017, vol. 10, # 1, p. 53 - 57
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Reference: [1] ChemSusChem, 2017, vol. 10, # 1, p. 53 - 57
  • 6
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  • [ 2280-44-6 ]
  • [ 6322-07-2 ]
  • [ 90-80-2 ]
Reference: [1] Helvetica Chimica Acta, 2000, vol. 83, # 12, p. 3211 - 3228
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Reference: [1] Journal of Catalysis, 2012, vol. 295, p. 15 - 21
  • 8
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  • [ 501-30-4 ]
Reference: [1] Bulletin of the Agricultural Chemical Society of Japan, 1929, vol. 5, p. 41,43[2] Chem. Zentralbl., 1930, vol. 101, # II, p. 579
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YieldReaction ConditionsOperation in experiment
2.04 g With oxygen In water for 93 h; Flow reactor; Microbiological reaction Example 1. L-Sorbose productionTime Medium D-sorbitolIn this example, Gluconobacter (hr) (ml) (g)0 0 0oxydans ATCC621 catalyzed the 15 4 0.1216.5 6 0.18partial oxidation of D-sorbitol to L- IS 7.5 0.22522.5 11 0.33sorbose with the stoichiometric 24.5 12.5 0.37542 23 0.69consumption of oxygen in a PFR47 26 0.78 Extraction similar to FIG. 3 run in upflow mode 54 32 0.96 D-sorbitol L-Sorbose Conversion73 41 1.23 (g) (g) ( ) A G. oxydans culture was grown at Total 93 68 2.04 0 0.57 100Table 1. Results of D-sorbitol conversion to L-sorbose. Only 30°C and 200 rpm in growth L-sorbose was detected in the liquid collection chamber medium to an ODeoo of 2.2, indicating 100percent conversion by the G. oxydans in the PFR. centrifuged at 4°C, 5,000 rpm, for 10 minutes. The 3 g wet cell pellet was resuspended in 7 mlSPP medium. The cells were then directly immobilized on the porous substrate 15x17.5 cm3 MM CHR chromatography paper (Cat. 3030-153; Whatman, part of GE Healthcare) with a paint brush. The liquid-contacting chamber of the PFR was supplied with SPP medium daily. The gas-contacting chamber was continuously supplied with humidified air generated by sparging through water prior to being sent through the gas-contacting chamber. The liquid-collection chamber was continuously flushed with air. Table 1 shows the liquid volumes of each liquid addition, cumulative D-sorbitol added, and the results of the extraction.
Reference: [1] Advances in Carbohydrate Chemistry, 1952, vol. 7, p. 109
[2] Chemische Berichte, 1933, vol. 66, p. 1251
[3] Journal of the American Chemical Society, 1936, vol. 58, p. 1012
[4] Arch.biol.Nauk, 1936, vol. 43, p. 210ff.[5] Chem. Zentralbl., 1938, vol. 109, # I, p. 4343
[6] Biochemische Zeitschrift, 1931, vol. 233, p. 139 - 211[7] Biochemische Zeitschrift, 1934, vol. 270, p. 7
[8] Iowa State College Journal of Science, 1946, vol. 21, p. 252,262[9] Chem.Abstr., 1947, p. 6299
[10] Industrial and Engineering Chemistry, 1937, vol. 29, p. 1385[11] Industrial and Engineering Chemistry, 1939, vol. 31, p. 1518
[12] Journal of the American Chemical Society, 1936, vol. 58, p. 1012
[13] Recueil des Travaux Chimiques des Pays-Bas, 1935, vol. 54, p. 861
[14] Archives of Biochemistry, 1946, vol. 9, p. 439,441
[15] Zhurnal Obshchei Khimii, 1939, vol. 9, p. 936,940[16] Chem. Zentralbl., 1940, vol. 111, # I, p. 872
[17] Mikrobiologija, 1942, vol. 11, p. 125[18] Chem.Abstr., 1944, p. 3313
[19] Mikrobiologija, 1937, vol. 6, p. 902[20] Chem. Zentralbl., 1938, vol. 109, # I, p. 3224
[21] Mikrobiologija, 1937, vol. 6, p. 899,900[22] Mikrobiologija, 1942, vol. 11, p. 115[23] Chem.Abstr., 1944, p. 3313[24] Chem. Zentralbl., 1938, vol. 109, # I, p. 3224
[25] Industrial and Engineering Chemistry, 1937, vol. 29, p. 1385[26] Industrial and Engineering Chemistry, 1939, vol. 31, p. 1518
[27] Journal of the American Chemical Society, 1936, vol. 58, p. 1012
[28] Recueil des Travaux Chimiques des Pays-Bas, 1935, vol. 54, p. 861
[29] Trudy Vitamin.Inst., 1956, vol. 5, p. 66[30] Chem.Abstr., 1957, p. 7491
[31] Journal of Research of the National Bureau of Standards (United States), 1957, vol. 59, p. 289,290
[32] Journal of Scientific and Industrial Research, 1951, vol. 10B, p. 7
[33] Biochemische Zeitschrift, 1935, vol. 280, p. 375
[34] Arch.biol.Nauk., 1936, vol. 43, # 2/3, p. 209[35] Chem. Zentralbl., 1938, vol. 109, # I, p. 4343
[36] Biochemische Zeitschrift, 1934, vol. 271, p. 61
[37] Zhurnal Obshchei Khimii, 1939, vol. 9, p. 936,940[38] Chem. Zentralbl., 1940, vol. 111, # I, p. 872
[39] Trudy Vitamin.Inst., 1956, vol. 5, p. 66[40] Chem.Abstr., 1957, p. 7491
[41] Mikrobiologija, 1942, vol. 11, p. 115[42] Chem.Abstr., 1944, p. 3313
[43] Mikrobiologija, 1937, vol. 6, p. 898[44] Chem.Abstr., 1939, p. 9355
[45] Nippon Nogei Kagaku Kaishi, 1944, vol. 20, p. 83[46] Chem.Abstr., 1948, p. 4711
[47] Nippon Nogei Kagaku Kaishi, 1949, vol. 23, p. 223[48] Chem.Abstr., 1951, p. 6793
[49] Chem. Zentralbl., 1911, vol. 82, # I, p. 996
[50] Bioscience, biotechnology, and biochemistry, 2002, vol. 66, # 1, p. 57 - 64
[51] Bioscience, biotechnology, and biochemistry, 2002, vol. 66, # 1, p. 57 - 64
[52] Patent: WO2013/74551, 2013, A1, . Location in patent: Page/Page column 42; 43
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Reference: [1] ChemSusChem, 2015, vol. 8, # 6, p. 970 - 973
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Reference: [1] ChemSusChem, 2015, vol. 8, # 6, p. 970 - 973
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Reference: [1] Archives of Biochemistry, 1946, vol. 9, p. 439,441
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Reference: [1] Bioscience, Biotechnology and Biochemistry, 1999, vol. 63, # 12, p. 2137 - 2143
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  • [ 135861-56-2 ]
YieldReaction ConditionsOperation in experiment
99% at 20℃; for 12 h; EXAMPLE 1
1,3:2,4-Bis(3',4'-dimethylbenzylidene) Sorbitol
To the white slurry of D-sorbitol (9.11 g, 50 mmol) and 3,4-dimethylbenzaldehyde (13.4 g, 100 mmol) in acetonitrile (100 mL) at room temperature was added a solid of p-toluenesulfonic acid monohydrate (1.9 g, 10 mmol).
After magnetically stirring for 12 h, the gel-like material (no visible solvent present) was washed sequentially with boiling water (200 mL*2), cyclohexane (200 mL*2) and boiling water (200 mL*4).
After drying in vacuum oven at 110° C. for 12 h, 1,3:2,4-bis(3',4'-dimethylbenzylidene) sorbitol (20.5 g, 99percent) was obtained as a white powder.
The product was properly characterized using 1H and 13C NMR, IR and GC/MS.
99% With trimethyl orthoformate In methanol at 20℃; for 48 h; EXAMPLE 8
1,3:2,4-Bis(3',4'-dimethylbenzylidene) Sorbitol
42.46 grams (0.226 mol) of D-sorbitol, 60.65 grams (0.45 mol, 2 eq) of 3,4-dimethylbenzaldehyde, 47.98 g (0.45 mol, 2 eq) of trimethyl orthoformate and 0.2 g of bismuth triflate hydrate are mixed with 560 ml of dry methanol, and the suspension is stirred at room temperature for 2 days.
The whole flask reaction mixture becomes thick gel-like (solidified).
After work up as described above, the product is obtained as white powder at similar yield (99percent) with similar purity as described in Example #7.
99% With trimethyl orthoformate In methanol at 20℃; for 49 h; Heating / reflux EXAMPLE 7
1,3:2,4-Bis(3',4'-dimethylbenzylidene) Sorbitol
42.46 grams (0.226 mol) of D-sorbitol, 60.65 grams (0.45 mol, 2 eq) of 3,4-dimethylbenzaldehyde, 47.98 g (0.45 mol, 2 eq) of trimethyl orthoformate and 0.11 g of bismuth triflate hydrate are mixed with 560 ml of dry methanol, and the suspension is heated to reflux for 1 hour to achieve a clear solution.
The whole mixture is then stirred at room temperature over the weekend (2 days).
The whole flask reaction mixture becomes thick gel-like (solidified), which is then added 300 ml of methanol, and the solid is collected by filtration.
After washing 6 times with 6*200 ml of boiling water, the white solid product is dried at room temperature for 2 days, and then dried overnight in a vacuum oven at 110° C. 93 gram (yield 99percent) of product is obtained as a white powder, with a GC-MS purity of 99.54percent and mp of 260C (dec.).
90.3%
Stage #1: With camphor-10-sulfonic acid In methanol at 20℃; for 48 h;
Stage #2: for 2 h;
Example 7 Preparation of a composition comprising pure 1,3:2,4-di(3,4-dimethylbenzylidene)-D-sorbitol and organosilane treated fume silica powders (0060) A 10 L four-necked cylindrical shaped reaction flask equipped with a thermometer, a nitrogen inlet, and a mechanical stirrer was charged with D-sorbitol (400 g, 2.20 moles), camphorsulfonic acid (12 g), 3,4-dimethyl-benzaldehyde (530 g, 3.95 moles) and methanol (4250 g), and then reacted at room temperature for 48 hours, so as to form a first reaction mixture. (0061) After neutralizing the first reaction mixture to pH 8, VenPure™, 20 grams of sodium borohydride solution having 12percent of NaBH4 effective amount, and 10.6 grams of an organosilane treated fume silica, CAB-O-SIL® TS720, were added gently in the first reaction mixture and stirred for 2 hours to form a precipitated product. The precipitated product was washed with a 40 wtpercent methanol solution to obtain a second reaction mixture. (0062) Finally, a solid substance was collected by filtration, dried and ground to give a composition (748.9 g) as white dispersive powders having 1,3:2,4-di(3,4-dimethylbenzylidene)-D-sorbitol and organosilane treated fume silica powders having a yield of 90.3percent, an ash content of 1.3 percent and a LC purity of 99.9percent. No 3,4-dimethyl-benzaldehyde was detected by the GC analysis, and the composition did not release any odor.
80% With methanesulfonic acid; choline chloride In methanol at 26℃; for 8 h; Example- 13; The choline chloride (1.4 gm) and methanesulfonicacid (MSA) (0.96 gms) were added to methanol (30 ml) and mixed well to prepare the ionic fluid. 3,4 dimethyl benzaldehyde (1.5 ml) and sorbitol (1.5 gm) were added to the ionic fluid and stirred to initiate the reaction at 26°C. The thick solid mass formed after few minutes of starting the reaction and the reaction was continued for 8 hrs. The solid product was filtered and washed with 100 ml diethylether. The white solid product was dried in oven at 95°C for 2 hrs followed by air dried for 4 hrs for measuring the yield. The yield and purity were found to be 80percent and 99.8percent respectively.
80% With methanesulfonic acid; choline chloride In methanol at 26℃; for 8 h; General procedure: EXAMPLE 13 [0095] The choline chloride (1.4 gm) and methanesulfonicacid (MSA) (0.96 gms) were added to methanol (30 ml) and mixed well to prepare the ionic fluid. 3,4 dimethyl benzaldehyde (1.5 ml) and sorbitol (1.5 gm) were added to the ionic fluid and stirred to initiate the reaction at 26° C. The thick solid mass formed after few minutes of starting the reaction and the reaction was continued for 8 hrs. The solid product was filtered and washed with 100 ml diethylether. The white solid product was dried in oven at 95° C. for 2 hrs followed by air dried for 4 hrs for measuring the yield. The yield and purity were found to be 80percent and 99.8percent respectively.
77% at 26℃; for 5 h; Example: 1; Toluene-4-sulphonic acid monohydrate (PTSA), a hydrogen donor (2gms) was mixed with sodium chloride (0.6 gms) in equal mole ratio and 30 ml methanol was added to the salt mixture and stirred well to prepare ionic fluid. The ionic fluid obtained was used for carrying out the dehydration reaction at 26°C. 3,4 dimethyl benzaldehyde and sorbitol in 2: 1 mole ratio were added to the ionic compound and stirred to initiate the reaction. The solid mass formed within few minutes of starting the reaction. The stirring speed was increased to keep the mass in suspension condition and reaction was continued for 5 hrs. The solid product was filtered to obtain mother liquor and a white solid mass. The white solid mass was washed with 120 ml methanol. The white solid product was dried in oven at 95°C for 2 hrs followed by air dried for 4 hrs for measuring the yield. The yield was found to be 77percent.
50% at 20℃; for 12 h; EXAMPLE 5
1,3:2,4-Bis(3',4'-dimethylbenzylidene) Sorbitol
To the white slurry of D-sorbitol (9.11 g, 50 mmol) and 3,4-dimethylbenzaldehyde (13.4 g, 100 mmol) in methanol (100 mL) at room temperature was added a solid of tin dichloride dihydrate (2.3 g, 10 mmol).
After magnetically stirring for 12 h, the gel-like material (no visible solvent present) was washed sequentially with boiling water (200 mL*2), cyclohexane (200 mL*2) and boiling water (200 mL*4).
After drying in vacuum oven at 110° C. for 12 h, 1,3:2,4-bis(3',4'-dimethylbenzylidene) sorbitol (10.3 g, 50percent) was obtained as a white powder.
The product was properly characterized using 1H and 13C NMR, IR and GC/MS.

Reference: [1] Patent: US2006/79720, 2006, A1, . Location in patent: Page/Page column 4
[2] Patent: US2006/79720, 2006, A1, . Location in patent: Page/Page column 5
[3] Patent: US2006/79720, 2006, A1, . Location in patent: Page/Page column 4-5
[4] Patent: US2006/79720, 2006, A1, . Location in patent: Page/Page column 4
[5] Patent: US2006/79720, 2006, A1, . Location in patent: Page/Page column 5
[6] Patent: EP2940023, 2015, A1, . Location in patent: Paragraph 0060-0062
[7] Patent: WO2012/95855, 2012, A1, . Location in patent: Page/Page column 19
[8] Patent: US2013/296580, 2013, A1, . Location in patent: Paragraph 0095
[9] Patent: WO2012/95856, 2012, A1, . Location in patent: Page/Page column 13-14
[10] Patent: US2006/79720, 2006, A1, . Location in patent: Page/Page column 5
[11] Patent: US2006/79720, 2006, A1, . Location in patent: Page/Page column 4
[12] Patent: US2006/79720, 2006, A1, . Location in patent: Page/Page column 4
[13] Patent: US2006/79720, 2006, A1, . Location in patent: Page/Page column 4
[14] Patent: US2006/79720, 2006, A1, . Location in patent: Page/Page column 4
[15] Patent: US2013/296581, 2013, A1, . Location in patent: Paragraph 0060
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