Isosorbide

Manufactured by Merck Group

Sourced in Germany

Isosorbide is a diol compound used as a building block in the production of various chemicals and materials. It is a colorless, crystalline solid with a molecular formula of C₆H₁₀O₄. Isosorbide serves as a versatile intermediate in the synthesis of pharmaceuticals, polymers, and other specialty chemicals.

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Dimethyl isosorbide (2 citations) Isosorbide dimethyl ether (2 citations)

8 protocols using isosorbide

Testosterone Propionate Toxicology Protocol

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Testosterone propionate (TP), bisphenol-A (BPA, CAS number 80-05-7), Isosorbide
(ISO, CAS number 652-67-5) and cyclohexanedimethanol (CHDM, CAS number 105-08-8)
and corn oil were purchased from Sigma Chemical Co. (St. Louis, MO, USA). All
substances were stored in glass containers at room temperature.

Kim H.S., Kim Y.B., Choi D., Cheon Y.P, & Lee S.H. (2017). Hershberger Assays for Bisphenol-A and Its Substitute Candidates. Development & Reproduction, 21(4), 441-448.

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Synthesis of bio-based polyesters

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2,5-Furandicarboxylic acid (FDCA, 98%) was purchased from TCI Chemicals (Zwijndrecht, Belgium). 1,12-Dodecanedioic acid (DDA 98%) was supplied by Fluka (Oeiras, Portugal). Dibutyltin(IV) oxide (DBTO) was purchased from TEGOKAT 248. Isosorbide (Is, 99%), titanium(IV) isopropoxide (Ti(OiPr)₄, 99.999%), deuterated chloroform (CDCl₃, 99.5 atom % D), lipase from porcine pancreas (PPL), and sea salts (NutriSelect^TM Basic) were obtained from Sigma–Aldrich (Oeiras, Portugal). Methanol (analytical grade), chloroform (HPLC grade), and sodium phosphate monobasic anhydrous (NaH₂PO₄) were provided by Fisher Scientific (Porto Salvo, Portugal). Sodium phosphate dibasic (Na₂HPO₄, 99+%) was acquired from ACROS Organics (Porto Salvo, Portugal). All chemicals and solvents were used as received without further purification.

Bouyahya C., Patrício R., Paço A., Lima M.S., Fonseca A.C., Rocha-Santos T., Majdoub M., Silvestre A.J, & Sousa A.F. (2022). Isosorbide and 2,5-Furandicarboxylic Acid Based (Co)Polyesters: Synthesis, Characterization, and Environmental Degradation. Polymers, 14(18), 3868.

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Synthesis and Characterization of Functional Monomers

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Isosorbide, 4-nitrobenzoyl chloride, aniline, and p-aminobenzoic acid were purchased from Sigma-Aldrich. Cinnamoyl chloride and N,N-di(hydroxyethyl)aniline were purchased from Alfa Aesar. Diglycidyl ether of bisphenol-A (MW = 392) was purchased as a commercial product from Shell Company. Deionized water (resistivity > 18.25 MΩ cm) was obtained from a Millipore water purification system. Glass slides were treated with the H₂SO₄/30% H₂O₂ (7 : 3) mixture (caution: this solution is extremely corrosive) for 3 h, rinsed with acetone and washed with plenty of deionized water for several times. Unless otherwise stated, all chemicals and solvents were purchased commercially and used directly without further purification. The synthesis and characterization details of BP-AZ-CA and IAC-4 have been reported in the previous articles,^{34,54 (link)} which can also be seen in the ESI.†

Li X., Huang H., Wu B., Liao C, & Wang X. (2021). Comparative study of photoinduced surface-relief-gratings on azo polymer and azo molecular glass films. RSC Advances, 11(55), 34766-34778.

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Formulation and Characterization of Biomaterials

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Isosorbide, ethylene carbonate, IPDI (Isophorone diisocyanate), TEGDMA (Triethylene glycol dimethacrylate), DBTBL (dibutyltin dilaurate), HEMA (2-hydroxyethyl methacrylate), penicillin/streptomycin, and L-glutamine were purchased from Sigma Aldrich (Darmstadt, Germany). α modified Eagle’s medium (α MEM), fetal bovine serum (FBS), and MesenPro medium were obtained from Gibco, Life Technologies Ltd., Paisley, UK.

Verisqa F., Cha J.R., Nguyen L., Kim H.W, & Knowles J.C. (2022). Digital Light Processing 3D Printing of Gyroid Scaffold with Isosorbide-Based Photopolymer for Bone Tissue Engineering. Biomolecules, 12(11), 1692.

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Isosorbide-Based Photopolymerizable Hydrogel

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Isosorbide(I) (98%), vanillin(V) (99%), methacrylic
anhydride (MAA) (≥94%), 4-(dimethylamino)pyridine (DMAP) (≥99%),
phenylbis(2,4,6-trimethylbenzoyl)-phosphine oxide (BAPO) (97%), hydrochloric
acid (HCl) (37%), and zinc acetate (Zn(OAc)₂) (99.99%)
were purchased from Sigma-Aldrich. 2,2′-(Ethylenedioxy)bis(ethylamine)
(Dom) (≥97%) and dichloromethane (DCM) (≥99%) were obtained
from Fisher Scientific and sodium bicarbonate (≥99.7%) from
Merck. Sodium hydroxide (NaOH) (99%), magnesium sulfate (MgSO₄) (≥99%), acetone (≥99%), ethanol (EtOH) (100%),
and deuterated chloroform (CDCl₃) (99.8 atom % D) were
received from VWR. All chemicals and solvents were used without any
additional purification.

Liguori A., Oliva E., Sangermano M, & Hakkarainen M. (2023). Digital Light Processing 3D Printing of Isosorbide- and Vanillin-Based Ester and Ester–Imine Thermosets: Structure–Property Recyclability Relationships. ACS Sustainable Chemistry & Engineering, 11(39), 14601-14613.

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Synthesis and Polymerization of Thiophosphoryl-Based Monomers

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The reagents used in the synthesis of monomers, thiophosphoryl chloride (PSCl 3 , 98%), fluorobenzene (99%), aluminum chloride anhydrous (AlCl 3 , 99%), morpholine (≥99.0%), N-methylpiperazine (≥99%) and triethylamine (Et 3 N, ≥99.5%) were purchased from Sigma-Aldrich. The reagents used for the polymerization, 2,2-bis(4-hydroxyphenyl)propane (bisphenol A, 99%, recrystallized from toluene), isosorbide (98%, recrystallized from acetone), anhydrous potassium carbonate and N,Ndimethylacetamide (DMAc, 99%) were purchased from Sigma-Aldrich. Other solvents were of reagent-grade quality and were used without further purification. Solutions of metallic ions were prepared from standard solutions for AAS in nitric acid (Sigma-Aldrich). Potassium citrate tribasic monohydrate (98%) was purchased from Sigma-Aldrich.

Chabbah T., Chatti S., Zouaoui F., Jlalia I., Gaiji H., Abderrazak H., Casabianca H., Mercier R., Weidner S.M., Errachid A., Marestin C, & Jaffrezic-Renault N. (2022). New poly(ether-phosphoramide)s sulfides based on green resources as sensitive films for the specific impedimetric detection of nickel ions. Talanta, 247.

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Synthesis of Isosorbide Dimethacrylate and Urethane Acrylate

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All chemicals used in this study were as follows: isosorbide (1,4:3,6-dianhydro-D-sorbitol, 98%), methacrylate anhydride (94%), ethyl 4-N,N-dimethylaminobenzoate (EDMAB), tetrahydrofuran (THF, anhydrous, 99.9%), and magnesium sulfate (MgSO4, 99.5%) were purchased from Sigma-Aldrich. Triethylamine (TEA) and 4,4-dimethylaminopyridine (DMAP) were purchased from Daejung for isosobide dimethacrylate (ISDM). Poly(tetramethylene ether)glycol (PTMG, average Mn 1000 g/mol), isophorone diisocyanate (IPDI, 98%), and diphenyl (2,4,6-trimethylbenzoyl)phosphine oxide (TPO, Shinyoun Rad Chem Ltd.) were also purchased from Aldrich, Korea, for the synthesis of PTMG-based urethane acrylate. ISDM (Fig. 1f) was synthesized as shown in Fig. S4^{33 (link)}.

Choi J.W., Kim G.J., Hong S., An J.H., Kim B.J, & Ha C.W. (2022). Sequential process optimization for a digital light processing system to minimize trial and error. Scientific Reports, 12, 13553.

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Fabric Treatment Compound Preparation

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Sorbitol, isosorbide, phosphoric acid (85%), dicyandiamide and urea were purchased from Sigma-Aldrich (Darmstadt, Germany). Respumit NF01 was sampled by Tanatex Chemicals (Ede, The Netherlands). Woven cotton fabric (150 g/m²), used for garments and technical applications, was purchased from Utexbel (Ronse, Belgium).

De Smet D., Wéry M., Bader M., Stachel I., Meyer M, & Vanneste M. (2021). Green Sorbitol- and Isosorbide-Based Flame Retardants for Cotton Fabrics. Materials, 14(21), 6375.

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