Dihydroartemisinin - ≥98%, mixture of α and β isomers , CAS No.81496-82-4

CAS: 81496-82-4 Cat. No.: D189218 Molecular Weight: 284.35

GRADE & PURITY ≥98%, mixture of α and β isomers

Synonyms

Dihydroartemisinin|71939-50-9|Artenimol|Cotexin|Dihydroqinghaosu|Alaxin|Cotecxin|Dihydroartemisinine|Salaxin|Santecxin|81496-82-4|Dynamax|(3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-ol|Di-hydroq

Storage

Room temperature

Shipped In

Normal

Specifications

Synonyms

Dihydroartemisinin | 71939-50-9 | Artenimol | Cotexin | Dihydroqinghaosu | Alaxin | Cotecxin | Dihydroartemisinine | Salaxin | Santecxin | 81496-82-4 | Dynamax | (3R, 5aS, 6R, 8aS, 9R, 10S, 12R, 12aR)-3, 6, 9-trimethyldecahydro-3H-3, 12-epoxy[1, 2]dioxepino[4, 3-i]isochromen-10-ol | Di-hydroq

Specifications & Purity

≥98%, mixture of α and β isomers

Storage

Room temperature

Shipped In

Normal

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488194133
• Canonical Smiles: CC1CCC2C(C(OC3C24C1CCC(O3)(OO4)C)O)C
• IUPAC Name: (1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-ol
• InChIKey: BJDCWCLMFKKGEE-ISOSDAIHSA-N
• INCHI: 1S/C15H24O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11+,12+,13-,14-,15-/m1/s1
• Isomeric SMILES: C[C@@H]1CC[C@H]2[C@H]([C@H](O[C@H]3[C@@]24[C@H]1CC[C@](O3)(OO4)C)O)C
• Molecular Weight: 284.35
• Reaxy-Rn: 25123268
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25123268&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Sesquiterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Sesquiterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Artemisinins
• Alternative Parents: Oxepanes Trioxanes Oxanes Hemiacetals Dialkyl peroxides Oxacyclic compounds Acetals Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Artemisinin skeleton - Oxepane - 1,2,4-trioxane - Oxane - Dialkyl peroxide - Hemiacetal - Oxacycle - Organoheterocyclic compound - Acetal - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as artemisinins. These are sesquiterpenoids originally isolated from the herb Artemisia annua. Their structure is based on artemisinin, a tetracyclic compound that contains a 1,2-dioxepane fused to an octahydrobenzopyran moiety. The internal peroxide bridge is believed to be a key to the mode of action of artemisinins.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Molecular Weight: 284.350 g/mol
• XLogP3: 2.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 284.162 Da
• Monoisotopic Mass: 284.162 Da
• Topological Polar Surface Area: 57.200 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 415.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Jingjing Zhen, Faguang Ma, Rongxin Lin, Ming Yan, Yilin Wu.  (2023)  Porous MOFs-based self-assembled membrane with specific rebinding nanocages for selective recognition and separation at molecular level.  DESALINATION,      [PMID:] [10.1016/j.desal.2023.117124]

2. Weibai Bian, Ruixuan Zhang, Xiaohui Chen, Chuanxun Zhang, Minjia Meng.  (2023)  Three-Dimensional Porous PVDF Foam Imprinted Membranes with High Flux and Selectivity toward Artemisinin/Artemether.  MOLECULES,  28  (21): (7452).  [PMID:37959871] [10.3390/molecules28217452]

3. Kaicheng Zhang, Rongxin Lin, Ming Yan, Yilin Wu.  (2023)  Click-chemistry synergic MXene-functionalized flexible skeleton membranes for accurate recognition and separation.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:37690308] [10.1016/j.jcis.2023.09.028]

4. Jing Yan, Faguang Ma, Yilin Wu.  (2023)  Permselective and transparent wooden membrane with artemisinin-imprinted nanocages based on a MOFs@C3N4 self-assembly design.  Materials Today Nano,      [PMID:] [10.1016/j.mtnano.2023.100369]

5. Jingsong Lu, Jing Yu, Wensheng Xie, Zhenhu Guo, Xiaohan Gao, Ying Li, Ziqing Zhang, Zeping Jin, Abdul Fahad, Shenglei Che, Lingyun Zhao, Yen Wei.  (2023)  Acidity-Triggered Charge-Convertible Conjugated Polymer for Dihydroartemisinin Delivery and Tumor-Specific Chemo-Photothermal Therapy.  ACS Applied Bio Materials,      [PMID:37190932] [10.1021/acsabm.3c00169]

6. Jing Yan, Kaicheng Zhang, Faguang Ma, Hang Cui, Yilin Wu.  (2023)  Scalable basswood-based PDA/GO-embedded self-assembly membrane within multilayered artemisinin-imprinted nanocage for high-selectivity cascading adsorption and transport.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2023.142277]

7. Wang Huai-Song, Xia Xingya, Wang Yingming, Lyu Weiping, Sang Mangmang, Gu Congcong, Liu Wenyuan, Zheng Feng.  (2021)  Anti-cancer adjuvant drug screening via epithelial-mesenchymal transition-related aptamer probe.  ANALYTICAL AND BIOANALYTICAL CHEMISTRY,  413  (28): (6951-6962).  [PMID:34676432] [10.1007/s00216-021-03669-x]

8. Yilin Wu, Wendong Xing, Minjia Meng, Jian Lu, Faguang Ma, Jia Gao, Xinyu Lin, Chao Yu.  (2020)  Multiple-functional molecularly imprinted nanocomposite membranes for high-efficiency selective separation applications: An imitated core-shell TiO2@PDA-based MIMs design.  COMPOSITES PART B-ENGINEERING,      [PMID:] [10.1016/j.compositesb.2020.108123]

9. Yao Yuyuan, Guo Qinglong, Cao Yue, Qiu Yangmin, Tan Renxiang, Yu Zhou, Zhou Yuxin, Lu Na.  (2018)  Artemisinin derivatives inactivate cancer-associated fibroblasts through suppressing TGF-β signaling in breast cancer.  JOURNAL OF EXPERIMENTAL & CLINICAL CANCER RESEARCH,  37  (1): (1-14).  [PMID:30477536] [10.1186/s13046-018-0960-7]

10. Shoubing Wang, Ziran Xu.  (2016)  Effects of Dihydroartemisinin and Artemether on the Growth, Chlorophyll Fluorescence, and Extracellular Alkaline Phosphatase Activity of the Cyanobacterium Microcystis aeruginosa.  PLoS One,  11  (10): (e0164842).  [PMID:27755566] [10.1371/journal.pone.0164842]

11. Shuangjie Zhu, Yongqi Cui, Huizheng Hu, Chenxi Zhang, Kan Chen, Zhongyan Shan, Weiping Teng, Jing Li.  (2025)  Dihydroartemisinin inhibits the development of autoimmune thyroiditis by modulating oxidative stress and immune imbalance.  FREE RADICAL BIOLOGY AND MEDICINE,      [PMID:39988064] [10.1016/j.freeradbiomed.2025.02.028]

12. Wei Wei, Xiaobing Ren, Fan Yi, Xuhui Zhang, Jiali Hou, Zhenxing Zhang, Liqian Yuan, Li Li, Qi Gao.  (2025)  Innovative Plant Exosome Delivery System for Enhancing Antiaging Potency on Skin.  ACS Applied Bio Materials,      [PMID:39992279] [10.1021/acsabm.4c01691]

13. Haoshen Wen, Yawei Li, Jiayi Luo, Wenhe Zhu, Geoff Hide, Xianmin Feng, Zhao-Rong Lun, De-Hua Lai.  (2025)  Effects of artesunate-loaded nanoparticles on Plasmodium berghei treatment in a mouse model.  ACTA TROPICA,      [PMID:40914236] [10.1016/j.actatropica.2025.107823]