86404-07-1Relevant articles and documents
Chemistry of L-ascorbic acid. IV. Regioselective O-alkylation of 5,6-O-isopropylidene-L-ascorbic acid using CsF
Kulkarni, Mukund G.,Kate, Sandesh D.
, p. 2365 - 2370 (2004)
The regioselective 3-O-alkylation of 5,6-O-isopropylidene-L-ascorbic acid is achieved under mild conditions using CsF as a base.
Synthesis of l-ascorbic acid-amino acid-norcantharidin conjugates and their biological activity evaluation in vitro
Wang, Xianheng,Wu, Caoyuan,Zhang, Jidong,Zhao, Changkuo,Zhou, Yiqi
supporting information, (2022/01/06)
Three components of L-ascorbic acid, amino acid and functionalized norcantharidins were constructed together in several steps to form 42 norcantharidin derivatives in a high yield. The structure of these synthesized l-ascorbic acid-amino acid-norcantharidin conjugates are determined by 1HNMR, 13CNMR and MS spectrum. The results showed that compounds 6e, 6g, 6j, 6l, 6m, 6b, 6e, 6i, and 6n showed high cytotoxicity to HepG2 and compounds 6b, 6e-g, 6l, 6n, 7b, 7d, 7h, 7i, 7n, 8g, 8i exhibited high cytotoxicity to SW480; Meanwhile, besides 6b, 6e, 6g, and 6k, the other compounds showed less toxic to LO2 at a concentration of 50 μg/mg after 72 h. Compound 6g can induce Mφ-type macrophages derived from mouse bone marrow to polarize to M1-type macrophages.
Synthesis and Biological Evaluation of Ascorbyl-Conjugated Peptide Derivatives as Collagen Synthesis Stimulating Agents in Human Skin Fibroblasts
Park, Kyeong-Yong,Kim, Jiyeon
, p. 2449 - 2456 (2020/02/11)
Vitamin C (ascorbic acid) is a widely used agent for anti-aging and whitening in the field of cosmetics. It affects collagen production in skin cells, inhibits melanin synthesis, displays anti-oxidant activity, and improves the immune system. However, vitamin C has limitations in cell permeability and environmental condition such as heating and lighting decrease its stability. Thus, vitamin C derivatives are being developed to overcome these problems. In this study, we synthesized vitamin C derivatives with a succinoyl group at the 2-position and peptides in the form of ester bonds. We then evaluated the cytotoxicity and collagen synthesis activity of these new compounds in human skin fibroblasts. Vitamin C-conjugated peptides were also synthesized in ether and carbamate forms, and the optimal combination conditions of vitamin C and peptides were identified. In addition, collagen synthesis-stimulating activity of vitamin C-conjugated peptides was also evaluated and compared to the effects of vitamin C alone. Based on these results, we confirmed that the ester-bonded vitamin C-conjugated peptide GEKG showed more stimulating effect on the production of collagen and related gene expression than either vitamin C or GEKG alone. This study will provide important information for developing skin health products and other topical cosmetics using vitamin C and peptides.
The Vitamin C Analogue 2-O-β-D-Glucopyranosyl-L-ascorbic Acid in Rhizomes, Stems and Leaves of Lycium barbarum
Amini-Rentsch, Lara,Andlauer, Wilfried,Bubloz, Carole,Marti, Roger,Micaux, Fabrice,Piantini, Umberto,Udrisard, Isabelle
, p. 828 - 830 (2020/12/01)
Awareness of health benefits of goji berries coming from their bioactive compounds, mostly antioxidants like ascorbic acid, has grown. Recently, an ascorbic acid analogue from goji berries, the 2-O-β-D-glucopyranosyl-l-ascorbic acid has been reported. In
Discovery of a stable vitamin C glycoside in crab apples (Malus sylvestris)
Richardson, Alistair T.,Cho, Jung,McGhie, Tony K.,Larsen, David S.,Schaffer, Robert J.,Espley, Richard V.,Perry, Nigel B.
, (2020/02/18)
Non-targeted LC-MS metabolomics on fruit of three wild and domesticated apple species (Malus sylvestris, M. sieversii and M. domestica) showed that two crab apple (M. sylvestris) accessions were distinguished by high concentrations of an ascorbic acid glycoside (AAG). This was partly purified, but key NMR signals were masked by inseparable sucrose. Reference samples of 2-O-β-D-glucopyranosyl L-ascorbic acid and 2-O-β-D-galactopyranosyl L-ascorbic acid were synthesised, but both coincided with the crab apple AAG on LC-MS. Peracetylation of the crab apple extract allowed both purification and characterisation, and the AAG was proven to be 2-O-β-D-glucopyranosyl L-ascorbic acid by comparison of 1H NMR, HRMS and HPLC data with synthesised peracetylated ascorbyl glycoside standards. The stability of the natural AA 2-β-glycoside was similar to synthetic 2-O-α-D-glucopyranosyl L-ascorbic acid, used widely in cosmetic and pharmaceutical products. This discovery in crab apples (Rosaceae) is only the fourth reported occurrence of any ascorbyl glycoside from plants, the others being from Cucurbitaceae, Solanaceae and Brassicaceae. It is hypothesised that AAGs may be more widespread in plants than currently realised.
COMPOUNDS AND COMPOSITIONS USEFUL AS RADIOTRACERS FOR IMAGING OF REACTIVE OXIDATIVE SPECIES
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Paragraph 0174; 0271, (2020/11/27)
Provided herein are compounds and compositions useful for imaging, detecting, and/or diagnosing oxidative stress and/or a ROS modulated illness by detection of gamma radiation emitted by the compound, as well as intermediate compounds and methods useful to make the compounds and/or compositions, and methods of use thereof.
Initial biological evaluations of 18F-KS1, a novel ascorbate derivative to image oxidative stress in cancer
Solingapuram Sai, Kiran Kumar,Bashetti, Nagaraju,Chen, Xiaofei,Norman, Skylar,Hines, Justin W.,Meka, Omsai,Kumar, J. V. Shanmukha,Devanathan, Sriram,Deep, Gagan,Furdui, Cristina M.,Mintz, Akiva
, (2019/05/27)
Background: Reactive oxygen species (ROS)-induced oxidative stress damages many cellular components such as fatty acids, DNA, and proteins. This damage is implicated in many disease pathologies including cancer and neurodegenerative and cardiovascular diseases. Antioxidants like ascorbate (vitamin C, ascorbic acid) have been shown to protect against the deleterious effects of oxidative stress in patients with cancer. In contrast, other data indicate potential tumor-promoting activity of antioxidants, demonstrating a potential temporal benefit of ROS. However, quantifying real-time tumor ROS is currently not feasible, since there is no way to directly probe global tumor ROS. In order to study this ROS-induced damage and design novel therapeutics to prevent its sequelae, the quantitative nature of positron emission tomography (PET) can be harnessed to measure in vivo concentrations of ROS. Therefore, our goal is to develop a novel translational ascorbate-based probe to image ROS in cancer in vivo using noninvasive PET imaging of tumor tissue. The real-time evaluations of ROS state can prove critical in developing new therapies and stratifying patients to therapies that are affected by tumor ROS. Methods: We designed, synthesized, and characterized a novel ascorbate derivative (E)-5-(2-chloroethylidene)-3-((4-(2-fluoroethoxy)benzyl)oxy)-4-hydroxyfuran-2(5H)-one (KS1). We used KS1 in an in vitro ROS MitoSOX-based assay in two different head and neck squamous cancer cells (HNSCC) that express different ROS levels, with ascorbate as reference standard. We radiolabeled 18F-KS1 following 18F-based nucleophilic substitution reactions and determined in vitro reactivity and specificity of 18F-KS1 in HNSCC and prostate cancer (PCa) cells. MicroPET imaging and standard biodistribution studies of 18F-KS1 were performed in mice bearing PCa cells. To further demonstrate specificity, we performed microPET blocking experiments using nonradioactive KS1 as a blocker. Results: KS1 was synthesized and characterized using 1H NMR spectra. MitoSOX assay demonstrated good correlations between increasing concentrations of KS1 and ascorbate and increased reactivity in SCC-61 cells (with high ROS levels) versus rSCC-61cells (with low ROS levels). 18F-KS1 was radiolabeled with high radiochemical purity (> 94%) and specific activity (~ 100 GBq/μmol) at end of synthesis (EOS). Cell uptake of 18F-KS1 was high in both types of cancer cells, and the uptake was significantly blocked by nonradioactive KS1, and the ROS blocker, superoxide dismutase (SOD) demonstrating specificity. Furthermore, 18F-KS1 uptake was increased in PCa cells under hypoxic conditions, which have been shown to generate high ROS. Initial in vivo tumor uptake studies in PCa tumor-bearing mice demonstrated that 18F-KS1 specifically bound to tumor, which was significantly blocked (threefold) by pre-injecting unlabeled KS1. Furthermore, biodistribution studies in the same tumor-bearing mice showed high tumor to muscle (target to nontarget) ratios. Conclusion: This work demonstrates the strong preliminary support of 18F-KS1, both in vitro and in vivo for imaging ROS in cancer. If successful, this work will provide a new paradigm to directly probe real-time oxidative stress levels in vivo. Our work could enhance precision medicine approaches to treat cancer, as well as neurodegenerative and cardiovascular diseases affected by ROS.
Method for synthesizing 3-O-alkyl-5,6-O-isopropylidene ascorbic acid by using circulation method
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Paragraph 0037; 0038, (2019/10/29)
The invention provides a method for synthesizing 3-O-alkyl-5,6-O-isopropylidene ascorbic acid by using a circulation method. The method comprises the following steps: enabling excessive 5,6-O-isopropylidene-ascorbic acid to react with an alkali and an alkyl reagent in a high-boiling-point polar aprotic solvent; after the reaction is completed, performing extraction with a low-polarity aprotic solvent; performing water washing treatment on the low-polarity aprotic solvent extraction liquid; performing concentration so as to obtain 3-O-alkyl-5,6-O-isopropylidene ascorbic acid; supplementing thealkali and the alkyl solvent into the high-boiling-point polar aprotic solvent extraction residue liquid; continuing a next batch of reactions for synthesizing the 3-O-alkyl-5,6-O-isopropylidene ascorbic acid; and performing deprotection on the 3-O-alkyl-5,6-O-isopropylidene ascorbic acid, so as to obtain 3-O-alkyl ascorbic acid. The method is good in selectivity, complete in raw material reaction, high in total yield and free of organic waste emission and has great industrial application values, and the synthesis cost can be greatly reduced.
A 2 - O - (2, 3, 4, 6 - four - O - acetyl - beta - D - glucopyranosyl) - 3 - O - benzyl - 5, 6 - O - isopropylidene - hematic preparation method
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Paragraph 0019, (2017/07/12)
The invention relates to a preparation method of 2-O-(2, 3, 4, 6-tetra-O-acetyl-Beta-D-glucopyranosyl)-3-O-benzyl-5, 6-isopropylidene-ascorbic acid. The preparation method includes: under catalysis of p-toluenesulfonic acid and under the condition of ice bath, allowing vitamin C and acetone to react for 3-5h, and performing filtering, washing and drying to obtain white solid of 5, 6-O-isopropylidene-L-ascorbic acid; adding mixture of benzyl bromide, alkali and the white solid of the 5, 6-O-isopropylidene-L-ascorbic acid into solvent, performing heating to allow reflux reaction for 3-5h, and washing and purifying reaction liquid to obtain 3-O-benzyl-5, 6-O-isopropylidene-L-ascorbic acid; dissolving the 3-O-benzyl-5, 6-O-isopropylidene-L-ascorbic acid with dichloromethane, dropwise adding dissolved solution into sodium hydroxide solution containing phase-transfer catalysts such as 2, 3, 4, 6-tetra-O-acetyl-Alpha-glucopyranosyl bromide and quaternary ammonium salts, and allowing reaction to obtain a product. The preparation method has the advantages that raw materials are easy to obtain, reaction conditions are moderate, the synthetic process is easy to control, yield is high, and the method has important applicable value.
Novel hybrid compounds of ascorbic acid and para-coumaric acid and compositions for skin whitening and wrinkle improvement comprising thereof
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Paragraph 0074- 0076, (2017/06/02)
The present invention relates to a hybrid compound of ascorbic acid with para-coumaric acid, and a composition for whitening skin and improving wrinkles comprising the same. More particularly, the present invention relates to a multi-functional cosmetic a
