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CAS No.: | 652-67-5 |
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Name: | Isosorbide |
Article Data: | 153 |
Molecular Structure: | |
Formula: | C6H10O4 |
Molecular Weight: | 146.143 |
Synonyms: | 1,4:3, 6-Dianhydro-D-glucitol;Hydronol;D-Glucitol, 1,4:3,6-dianhydro-;AT-101;Vascardin dinitrate;(1S,2S,5S,6R)-4,8-dioxabicyclo[3.3.0]octane-2,6-diol;Sorbid;(+)-D-Isosorbide;(1R,2S,5S,6R)-4,8-dioxabicyclo[3.3.0]octane-2,6-diol;Ismotic (TN);Devicoran;Glucitol, 1,4:3,6-dianhydro-, D-;Isosorbide (JP14/USP);D-Isosorbide; |
EINECS: | 211-492-3 |
Density: | 1.475 g/cm3 |
Melting Point: | 60-63 °C(lit.) |
Boiling Point: | 372.1 °C at 760 mmHg |
Flash Point: | 178.8 °C |
Solubility: | Soluble in alcohols, water and ketones. |
Appearance: | off-white to light yellow or beige crystal |
Risk Codes: | 22 |
Safety: | 24/25 |
PSA: | 58.92000 |
LogP: | -1.49420 |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene; carbonic acid dimethyl ester In methanol at 90℃; for 48h; Time; Large scale; | 98% |
With sulfuric acid In water at 150℃; under 75.0075 Torr; for 3h; Reagent/catalyst; | 96.1% |
With silica-alumina In water at 244.84℃; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With SA-SiO2-60.5 at 120℃; under 7.50075 Torr; for 10h; Reagent/catalyst; | A n/a B n/a C 84% |
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen; triethylamine In ethanol; water at 0℃; under 2250.23 Torr; for 12h; Autoclave; | A 81.55% B 16.1% |
Conditions | Yield |
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zinc(II) chloride In 1-methyl-3-octylimidazol-3-ium chloride at 150℃; for 1h; Product distribution / selectivity; | A 3.8% B 76% |
With zirconium phosphate In neat (no solvent) at 210℃; for 2h; Catalytic behavior; Temperature; Time; Reagent/catalyst; Inert atmosphere; Autoclave; | A 73% B n/a |
With hydrogen; palladium on activated charcoal at 160℃; under 2311.54 Torr; for 6h; Product distribution / selectivity; Autoclave; Neat (no solvent); | A 72.68% B 2.1% |
Conditions | Yield |
---|---|
With H-beta zeolite In neat (no solvent) at 126.84℃; under 525.053 Torr; for 2h; Catalytic behavior; Reagent/catalyst; | A n/a B 76% |
D-sorbitol
A
2,5-anhydro-d-sorbitol
B
Isosorbide
D
3,6-anhydro-D-glucitol
E
2,5-anhydro-D-mannitol
Conditions | Yield |
---|---|
sulfuric acid In water at 125 - 145℃; under 18 - 20 Torr; Industry scale; | A n/a B 75% C n/a D n/a E n/a |
Conditions | Yield |
---|---|
With sulfuric acid In water at 200℃; under 30003 Torr; for 6h; Autoclave; | A 8% B 73% |
D-sorbitol
A
2,5-anhydro-d-sorbitol
B
Isosorbide
C
1,5-anhydro-D-glucitol
Conditions | Yield |
---|---|
With Amberlyst-15 at 120℃; under 7.50075 Torr; for 10h; Reagent/catalyst; | A n/a B 71% C n/a |
Conditions | Yield |
---|---|
With hydrogen; phosphotungstic acid; palladium on activated charcoal In water at 160℃; under 2311.54 Torr; for 20h; Product distribution / selectivity; Autoclave; | A 13.06% B 70.33% C 5.73% |
With hydrogen; palladium dichloride at 160℃; under 2311.54 Torr; for 6h; Product distribution / selectivity; Autoclave; Neat (no solvent); | A 24.89% B 55.76% C 0.61% |
Isosorbide
Conditions | Yield |
---|---|
With pyridine hydrochloride at 185℃; for 10h; | 67% |
With carbonic acid dimethyl ester In 1,4-dioxane; methanol at 120℃; | 1.07 g |
With zinc(II) chloride at 300℃; under 71257.1 Torr; for 0.05h; Temperature; Pressure; Autoclave; | |
With 4-methyl-2-pentanone at 170℃; for 1h; Autoclave; | 97.5 %Chromat. |
The Hydronol, with its CAS registry number 652-67-5, has the IUPAC name of (3S,3aR,6R,6aR)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol. This is a kind of off-white to light yellow or beige crystal, and it is often used as the diuretic. When you swallow it, it will be harmful, and you should avoid contacting skin and eyes.
The characteristics of Hydronol are as follows: (1)ACD/LogP: -1.75; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.75; (4)ACD/LogD (pH 7.4): -1.75; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 2.65; (8)ACD/KOC (pH 7.4): 2.65; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 36.92; (13)Index of Refraction: 1.562; (14)Molar Refractivity: 32.11 cm3; (15)Molar Volume: 99 cm3; (16)Polarizability: 12.73×10-24 cm3; (17)Surface Tension: 56.6 dyne/cm; (18)Density: 1.475 g/cm3; (19)Flash Point: 178.8 °C; (20)Enthalpy of Vaporization: 71.64 kJ/mol; (21)Boiling Point: 372.1 °C at 760 mmHg; (22)Vapour Pressure: 4.71E-07 mmHg at 25°C; (23)Exact Mass: 146.057909; (24)MonoIsotopic Mass: 146.057909; (25)Topological Polar Surface Area: 58.9; (26)Heavy Atom Count: 10; (27)Complexity: 122.
In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: C1C(C2C(O1)C(CO2)O)O
(2)Isomeric SMILES: C1[C@H]([C@@H]2[C@H](O1)[C@H](CO2)O)O
(3)InChI: InChI=1S/C6H10O4/c7-3-1-9-6-4(8)2-10-5(3)6/h3-8H,1-2H2/t3-,4+,5-,6-/m1/s1
(4)InChIKey: KLDXJTOLSGUMSJ-JGWLITMVSA-N
Below are the toxicity information of this chemical:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 13600mg/kg (13600mg/kg) | Drugs in Japan Vol. 6, Pg. 71, 1982. | |
mouse | LD50 | intravenous | 6870mg/kg (6870mg/kg) | BRAIN AND COVERINGS: CHANGES IN CEREBRAL SPINAL FLUID | Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 15, 1969. |
mouse | LD50 | oral | 289mg/kg (289mg/kg) | Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 187, 1969. | |
rat | LD50 | intravenous | 11gm/kg (11000mg/kg) | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64(4), Pg. 158S, 1968. | |
rat | LD50 | oral | 24150mg/kg (24150mg/kg) | Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 15, 1969. |