Dihydroartemisinin - Moligand™, ≥98% , CAS No.71939-50-9

CAS: 71939-50-9 Cat. No.: D140839 Molecular Weight: 284.35 EC Number: 615-698-8

GRADE & PURITY Moligand™, ≥98%

Synonyms

β-Dihydroartemisinin | (3R,5aS,6R,8aS,9R,12R,12aR)-Decahydro-10-hydroxy-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin | Alaxin | Cotecxin | Cotexin | DHQHS 2 | Dihydroartemisinine | Dihydroqinghaosu.

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

Dihydro Artemisinin is an active antimalarial metabolite. Dihydro Artemisinin is also the main metabolite of Artemisinin, Arteether, Artemether, Artesunate.
An active antimalarial metabolite

Specifications

Synonyms

β-Dihydroartemisinin | (3R, 5aS, 6R, 8aS, 9R, 12R, 12aR)-Decahydro-10-hydroxy-3, 6, 9-trimethyl-3, 12-epoxy-12H-pyrano[4, 3-j]-1, 2-benzodioxepin | Alaxin | Cotecxin | Cotexin | DHQHS 2 | Dihydroartemisinine | Dihydroqinghaosu.

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Induces cell cycle arrest and inhibits cell migration in cancer cells. Depletes cellular iron via transferrin receptor 1. Antimalarial and antitumor agent. Orally active. Active in vivo and in vitro .

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504762275
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504762275
• 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
• RTECS: KD4165550
• Alternate CAS: 81496-82-4
• 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

• Solubility: Soluble in DMSO (57 mg/ml) at 25 °C, ethanol (14 mg/ml) at 25 °C, and water (<1 mg/ml) at 25 °C.
• Sensitivity: air & heat sensitive
• Melt Point(°C): 145-150℃
• 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

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