Citation: Hai Shan Jin, Li Ming Zhao. A contribution to the study of the modified Marschalk reaction:Hydroxymethylation of 6,8-O-dimethyl emodin[J]. Chinese Chemical Letters, ;2010, 21(5): 568-571. doi: 10.1016/j.cclet.2010.01.013 shu

A contribution to the study of the modified Marschalk reaction:Hydroxymethylation of 6,8-O-dimethyl emodin

School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116, China

Received Date: 17 November 2009

Fund Project: This work was supported by Natural Science Foundation of Xuzhou Normal University (No. 08XLB08), Science and Technology Project of Xuzhou (No. XJ09078) and Universities Natural Science Foundation of Jiangsu Province (No. 09KJD150006).

Hydroxymethylation of 6,8-O-dimethyl emodin was easily achieved in good yields by the modified Marschalk reaction. The influence of the amount of solvent, base and formaldehyde toward the hydroxymethylation was discussed. The results showed that a relatively dilute reaction solution facilitated the generation of the desired 2-hydromethyl product, while the thick reaction solution benefited the generation of the methylated quinizarins.
- Marschalk reaction,
- Hydroxymethylation,
- Emodin,
- Antitumor activity
1. [1]
  Shuang Li , Penghui Yuan , Xinyi Zhang , Meiru Liu , Dezhi Yang , Linglei Kong , Li Zhang , Yang Lu , Guanhua Du . Revolutionizing sepsis therapy: Machine learning-driven co-crystallization reveals emodin's therapeutic potential. Chinese Chemical Letters, 2026, 37(2): 111289-. doi: 10.1016/j.cclet.2025.111289
2. [2]
  Fengqing Wang , Changxing Qi , Chunmei Chen , Qin Li , Qingyi Tong , Weiguang Sun , Zhengxi Hu , Minyan Wang , Hucheng Zhu , Lianghu Gu , Yonghui Zhang . Discovery and enantioselective total synthesis of antitumor agent asperfilasin A via a regio- and diastereoselective Nazarov cyclization. Chinese Chemical Letters, 2025, 36(6): 110252-. doi: 10.1016/j.cclet.2024.110252
3. [3]
  Di ZHANG , Tianxiang XIE , Xu HE , Wanyu WEI , Qi FAN , Jie QIAO , Gang JIN , Ningbo LI . Construction and antitumor activity of pH/GSH dual-responsive magnetic nanodrug. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 786-796. doi: 10.11862/CJIC.20240329
4. [4]
  Haifeng ZHENG , Xingzhe GUO , Yunwei WEI , Xinfang WANG , Huimin QI , Yuting YAN , Jie ZHANG , Bingwen LI . Post-synthetic modification strategy to construct Co-MOF composites for boosting oxygen evolution reaction activity. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 193-202. doi: 10.11862/CJIC.20250029
5. [5]
  Zhi-Lin Wu , Rong-Nan Yi , Chunlin Zhuang . Electrochemical synthesis strategy for the development of antitumor selenoheterocyclic compounds. Chinese Chemical Letters, 2025, 36(10): 111408-. doi: 10.1016/j.cclet.2025.111408
6. [6]
  Jing Zhang , Charles Wang , Yaoyao Zhang , Haining Xia , Yujuan Wang , Kun Ma , Junfeng Wang . Application of magnetotactic bacteria as engineering microrobots: Higher delivery efficiency of antitumor medicine. Chinese Chemical Letters, 2024, 35(10): 109420-. doi: 10.1016/j.cclet.2023.109420
7. [7]
  Jin Wang , Xiaoyan Pan , Junyu Zhang , Qingqing Zhang , Yanchen Li , Weiwei Guo , Jie Zhang . Active molecule-based theranostic agents for tumor vasculature normalization and antitumor efficacy. Chinese Chemical Letters, 2024, 35(8): 109187-. doi: 10.1016/j.cclet.2023.109187
8. [8]
  Zhaomin Tang , Qian He , Jianren Zhou , Shuang Yan , Li Jiang , Yudong Wang , Chenxing Yao , Huangzhao Wei , Keda Yang , Jiajia Wang . Active-transporting of charge-reversal Cu(Ⅱ)-doped mesoporous silica nanoagents for antitumor chemo/chemodynamic therapy. Chinese Chemical Letters, 2024, 35(7): 109742-. doi: 10.1016/j.cclet.2024.109742
9. [9]
  Hu Wu , Ge Cao , Mingyang Liu , Hainan Xu , Meng Li , Hanwei Huang , Yujie Liu , Xu Zhao , Xifeng Qin , Onder Ergonul , Füsun Can , Funan Liu , Zhiqing Pang , Jiaming Zhu . Tumor cell membrane biomimetic liposomes-coated oncolytic viruses to target the homotypic tumor and augment the antitumor efficacy. Chinese Chemical Letters, 2025, 36(7): 110493-. doi: 10.1016/j.cclet.2024.110493
10. [10]
  Yongjuan Li , Rongrong Zhu , Yichen Guo , Yayun Wang , Rong Ma , Kunru Ma , Yongxing Zhao , Weijing Yang . Sequential-gated transformable nanoprodrug potentiates antitumor immunity through TME modulation and STING activation. Chinese Chemical Letters, 2025, 36(9): 110704-. doi: 10.1016/j.cclet.2024.110704
11. [11]
  Zerong Pei , Suyun Hu , Huimin Wei , Liqin Ding , Jingbo Liu , Fengyun Li , Hongyu Chen . Multifunctional carrier-free nanodrugs for enhanced delivery and efficacy of hydrophobic antitumor drugs. Chinese Chemical Letters, 2026, 37(1): 110981-. doi: 10.1016/j.cclet.2025.110981
12. [12]
  Xuanbo Zhang , Feng Fang , Na Li , Huicong Zhang , Kaiyuan Wang , Zhiqiang Yu , Jin Sun . From reversible to irreversible: Albumin-hitchhiking gemcitabine prodrugs for enhanced antitumor efficacy and reduced toxicity. Chinese Chemical Letters, 2026, 37(2): 111452-. doi: 10.1016/j.cclet.2025.111452
13. [13]
  Guangyao Wang , Zhitong Xu , Ye Qi , Yueguang Fang , Guiling Ning , Junwei Ye . Electrospun nanofibrous membranes with antimicrobial activity for air filtration. Chinese Chemical Letters, 2024, 35(10): 109503-. doi: 10.1016/j.cclet.2024.109503
14. [14]
  Hong-Tao Ji , Yu-Han Lu , Yan-Ting Liu , Yu-Lin Huang , Jiang-Feng Tian , Feng Liu , Yan-Yan Zeng , Hai-Yan Yang , Yong-Hong Zhang , Wei-Min He . Nd@C₃N₄-photoredox/chlorine dual catalyzed synthesis and evaluation of antitumor activities of 4-alkylated sulfonyl ketimines. Chinese Chemical Letters, 2025, 36(2): 110568-. doi: 10.1016/j.cclet.2024.110568
15. [15]
  Yixin Sun , Keke Yu , Xiuchun Guo , Lanlan Zong , Zhonggui He , Xiaohui Pu . Three-in-one reduction and acid-ignited micelles amplify antitumor efficacy via precise synergistic delivery of paclitaxel and naringenin. Chinese Chemical Letters, 2025, 36(6): 110393-. doi: 10.1016/j.cclet.2024.110393
16. [16]
  Yu-Chen Fang , Jia-He Chen , Mi-Zhuan Li , Hui-Min Li , Mei Bai , Yong-Zheng Chen , Zi-Wei Gao , Wen-Yong Han . Forging of silaoxycarbocyclics by interrupted Catellani reaction. Chinese Chemical Letters, 2025, 36(7): 110474-. doi: 10.1016/j.cclet.2024.110474
17. [17]
  Ting Wang , Xin Yu , Yaqiang Xie . Unlocking stability: Preserving activity of biomimetic catalysts with covalent organic framework cladding. Chinese Chemical Letters, 2024, 35(6): 109320-. doi: 10.1016/j.cclet.2023.109320
18. [18]
  Fangping Yang , Jin Shi , Yuansong Wei , Qing Gao , Jingrui Shen , Lichen Yin , Haoyu Tang . Mixed-charge glycopolypeptides as antibacterial coatings with long-term activity. Chinese Chemical Letters, 2025, 36(2): 109746-. doi: 10.1016/j.cclet.2024.109746
19. [19]
  Chong Liu , Ling Li , Jiahui Gao , Yanwei Li , Nazhen Zhang , Jing Zang , Cong Liu , Zhaopei Guo , Yanhui Li , Huayu Tian . The study of antibacterial activity of cationic poly(β-amino ester) regulating by amphiphilic balance. Chinese Chemical Letters, 2025, 36(2): 110118-. doi: 10.1016/j.cclet.2024.110118
20. [20]
  Qiong-Hui Peng , Ning-Bo Li , Jia-Cheng Hou , Cai-Jun He , Ya-Xin Yang , Chun-Lin Zhuang , Li-Juan Ou , Mei Yuan , Wei-Min He . Nd@g-C₃N₄ dual-functional photosynthesis and antitumor activities of 3-fluoroalkylated quinoxalin-2(1H)-ones. Chinese Chemical Letters, 2025, 36(12): 111402-. doi: 10.1016/j.cclet.2025.111402

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(1319)
HTML views(56)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return