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13042-39-2Relevant academic research and scientific papers
Volatile short-chain amphiphiles derived from isosorbide: Hydrotropic properties of esters vs. ethers
Lavergne, Aurelie,Moity, Laurianne,Molinier, Valerie,Aubry, Jean-Marie
, p. 5997 - 6007 (2013)
Two series of short-chain isosorbide monoalkanoates, differing from the free hydroxyl position, were synthesized and evaluated as volatile non-ionic hydrotropes, also known as solvo-surfactants . Their aqueous solubilities, solubilizing efficiencies and volatilities were evaluated and compared to the corresponding 5-O-alkylisosorbides. Whatever the acylation position (5-O- or 2-O-), isosorbide monoalkanoates are poorly water-soluble for acyl chains longer than four carbons, whereas 5-O-alkylisosorbides are completely miscible with water up to a pentyl chain, which seems to indicate that an ether link brings more hydrophilicity than an ester bond for these types of molecules. The shorter isosorbide monoalkanoates are completely miscible with water and the butanoates are particularly efficient in terms of aqueous solubilization of hydrophobic compounds. In addition, all hydrotropes exhibit some volatility albeit being non-VOC and contrarily to their ethers homologues, isosorbide alkanoates are easily hydrolysed in basic medium, which suggests a good biodegradability.
Method for preparing 2-acetic acid-5-isosorbide dinitrate from sorbitol
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Paragraph 0043-0056, (2021/05/08)
The invention discloses a method for preparing 2-acetic acid-5-isosorbide dinitrate from sorbitol, which comprises the following steps of: contacting a material containing sorbitol, an acetylating agent and a nitrating agent with a solid acid catalyst, and carrying out acylation reaction and nitration reaction to obtain the 2-acetic acid-5-isosorbide dinitrate. According to the method, sorbitol is subjected to one-pot conversion to prepare 2-acetic acid-5-isosorbide dinitrate, so that the operation process is greatly simplified, and the synthesis efficiency is improved; the used solid acid catalyst has small corrosion to equipment and is easily separated from a product; and the reaction conditions are mild, and high-vacuum, high-temperature and other high-energy-consumption operations are avoided.
Method for synthesizing isohexitol ester
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Paragraph 0010; 0043-0050; 0055-0056, (2021/05/05)
The invention discloses a method for synthesizing isohexitol ester, which is characterized in that a material containing hexitol and an esterifying agent is contacted with a solid acid catalyst in the presence of an aprotic solvent, and the isohexitol ester is obtained through one-pot one-step reaction. The method is especially suitable for the reaction of directly synthesizing the isohexitol ester, especially isosorbide ester, from hexitol, especially sorbitol, the total yield of the obtained isohexitol ester is 80% or above, and the yield of the isosorbide dicarboxylate reaches 60% or above.
Selective Methylmagnesium Chloride Mediated Acetylations of Isosorbide: A Route to Powerful Nitric Oxide Donor Furoxans
Kielty, Patrick,Smith, Dennis A.,Cannon, Peter,Carty, Michael P.,Kennedy, Michael,McArdle, Patrick,Singer, Richard J.,Aldabbagh, Fawaz
, p. 3025 - 3029 (2018/05/28)
Isosorbide was functionalized with furoxan for the first time to give adducts that release nitric oxide up to 7.5 times faster than the commercial vasodilator, isosorbide-5-mononitrate (Is5N). The synthesis was facilitated by MeMgCl-mediated selective acetylation of isosorbide or selective deacetylation of isosorbide-2,5-diacetate, which was rationalized in terms of a more stable 5-alkoxide magnesium salt using DFT. Isosorbide-furoxans are safer to handle than Is5N due to greater thermal stability.
Development of a Practical Enzymatic Synthesis of Isosorbide-2-acetate
Zhu, Shi-Guo,Huang, Jia-Xin,Zhang, Gui-Min,Chen, Shao-Xin,Zhang, Fu-Li
, p. 1548 - 1552 (2018/11/25)
Using immobilized lipase, we developed an enzymatic synthesis of isosorbide-2-acetate (1), a key intermediate in the preparation of isosorbide-5-mononitrate. 1 was prepared in high yield (～92%) with excellent regioselectivity (>99.5% d.e.) through hydrolysis (Novozym 435) or alcoholysis (lipase PS IM) of isosorbide-2,5-diacetate. The conditions for the enzymatic process were optimized. The substrate concentration could be 400-500 g/L, and the enzyme to substrate ratio was 10 wt %. The feasibility of enzyme recycling was also demonstrated. In addition, the enzymatic process was carried out on a kilogram scale and was proved to be scalable, efficient, and economical.
COMPOUNDS AND COMPOSITIONS FOR USE IN TREATING PSORIASIS
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Paragraph 0084, (2018/10/19)
Compounds and pharmaceutical compositions for use in the treatment of psoriasis are disclosed. Preferred compounds have demonstrated efficacy in reducing skin scaling, erythema and skin thickness in the mouse model of Aldara-induced psoriasis.
ISOSORBIDE-BASED POLYMETHACRYLATES
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Paragraph 0135-0136, (2016/09/12)
A monomer comprises the structure wherein R1 comprises H or a substituted hydrocarbyl or unsubstituted hydrocarbyl, and wherein R2 comprises H, a halide, or a substituted or unsubstituted (C1-C4) hydrocarbyl. A method comprises (a) reacting a dianhydrohexitol precursor having the structure with an acyl-group containing compound having the structure wherein R1 comprises H or a substituted hydrocarbyl or unsubstituted hydrocarbyl, and X comprises a halide, a hydroxyl group, or an acyl group to form an acylated dianhydrohexitol ester intermediate having the structure and (b) reacting the acylated dianhydrohexitol ester intermediate with an acrylic-based compound having the structure wherein R2 comprises H, a halide, or a substituted or unsubstituted (C1-C4) hydrocarbyl, and Y comprises a halide, a hydroxyl group, or an acyl group, to form a dianhydrohexitol-based monomer having the structure
Isohexide hydroxy esters: Synthesis and application of a new class of biobased AB-type building blocks
Thiyagarajan, Shanmugam,Wu, Jing,Knoop, Rutger J. I.,Van Haveren, Jacco,Lutz, Martin,Van Es, Daan S.
, p. 47937 - 47950 (2014/12/10)
Here we present the synthesis of a new family of sugar derived 1,4:3,6-dianhydrohexitol based AB-type monomers, containing one methyl ester group and a secondary hydroxyl group in all four possible stereo isomers (RR, RS, SR, SS). Structural characterization of the monomers (5a-d) was established by 1D and 2D NMR analysis, which was further confirmed by single-crystal X-ray structure determination. The application of these monomers in step-growth polymerization afforded fully isohexide based stereo-regular polyesters. Homo polyesters based on the RR and RS monomers were obtained with reasonable molecular weights by melt polymerization (Mn 2400 and 2500 resp.). These materials showed unexpectedly low glass-transition temperatures of 20°C and 15°C respectively. In contrast, the monomers with SR and SS configuration yielded only low molecular weight oligomers. Surprisingly, copolymerization of the RR and SR monomers gave a polyester with higher molecular weight (Mn 4100) and a high Tg of 80°C. These preliminary results show that isohexide hydroxyesters are an intriguing new class of biobased building blocks with many potential applications.
PRODUCTION OF 5-MEMBERED AND 6-MEMBERED CYCLIC ESTERS OF POLYOLS
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Page/Page column 10-11, (2010/01/12)
Described herein are improved methods for the preparation of 5- and 6-membered cyclic mono and diesters of sugar alcohols and anhydrosugar alcohols by reaction with an organic acid RCOOH over a solid acidic substrate. The process is adaptable to a continuous process for simultaneously making and separating the cyclic esters from the sugar alcohols and anhydrosugar alcohols under mild conditions using the solid acid substrate as both the catalyst and a chromatographic bed for separation. The reactions are performed at mild temperatures of 700C to 10O0C and the formation of the cyclic esters is nearly quantitative. Also described is a method for making 5- and 6-membered cyclic mono and diesters of sugar alcohols and anhydrosugar alcohols using microwave irradiation in the presence of the organic acid.
Asymmetric synthesis of β-lactams by [2+2] cycloaddition using 1,4:3,6-dianhydro-d-glucitol (isosorbide) derived chiral pools
Shaikh,Kale,Shaikh, Md. Abrar,Puranik, Vedavati G.,Deshmukh
, p. 3380 - 3388 (2007/10/03)
Highly diastereoselective synthesis of cis-β-lactams via [2+2] cycloaddition reactions of imines derived from a chiral bicyclic aldehyde and ketenes is described. The chiral bicyclic aldehyde as well as chiral acids were prepared from commercially available inexpensive isosorbide. The cycloaddition reaction was found to be highly diastereoselective; in some cases giving a single diastereomer of cis-azetidin-2-one in very good yields. A moderate diastereoselectivity was observed with chiral ketenes derived from isosorbide.
