DHQHS 2 Chemical Properties

Melting point:

144-149°C

Boiling point:

375.6±42.0 °C(Predicted)

Density 

1.24

storage temp. 

Inert atmosphere,2-8°C

solubility 

DMSO : 41.67 mg/mL (146.54 mM; Need ultrasonic)

pka

12.61±0.70(Predicted)

form 

solid

color 

White to Almost white

Merck 

14,817

InChI

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

InChIKey

BJDCWCLMFKKGEE-ISOSDAIHSA-N

SMILES

O1[C@]23[C@@]4([H])O[C@@](C)(CC[C@@]2([H])[C@H](C)CC[C@@]3([H])[C@@H](C)[C@@H](O)O4)O1

CAS DataBase Reference

71939-50-9(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

2

RTECS 

KD4165550

HS Code 

29329990

MSDS

• Language:English Provider:SigmaAldrich

DHQHS 2 Usage And Synthesis

Chemical Properties

White Solid

Uses

The main metabolite of Artemisinin, Arteether, Artemether, Artesunate. An active antimalarial metabolite

Definition

ChEBI: Artenimol is an artemisinin derivative.

Synthesis

The general procedure for the synthesis of (3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3H-3,12-epoxy[1,2]dioxahepta[4,3-i]isochromene-10-ol from artemisinin was carried out as follows: under nitrogen protection, a solution of LiBHEt3 (a 1 M solution of tetrahydrofuran) was passed through a syringe was slowly added dropwise to a solution of artemisinin (200 mg, 0.71 mmol) dissolved in anhydrous tetrahydrofuran (20 mL). The temperature of the reaction mixture was maintained constant during the reaction by means of a water or ice water bath. The progress of the reaction was monitored by thin layer chromatography (TLC) until the artemisinin was completely consumed (about 5-10 min). Subsequently, THF solution of acetic acid (20 vol%, 100 μL or 50 μL at a time) was added in batches to quench the reaction and the pH of the reaction mixture was adjusted to 5-6. The reaction mixture was concentrated to dryness under reduced pressure. The dried residue was separated by extraction with ethyl acetate and distilled water. After separation of the organic phase, the aqueous phase was extracted twice more with ethyl acetate. All ethyl acetate extracts were combined and dried with anhydrous sodium sulfate for 6 hours. The dried organic phase was filtered and concentrated to dryness under reduced pressure to give a white flaky target product.

in vivo

IC 50

RelA; Plasmodium; Autophagy

References

[1] Molecules, 2011, vol. 16, # 6, p. 4527 - 4538
[2] Journal of the Chemical Society. Perkin Transactions 1, 2001, # 19, p. 2421 - 2429
[3] Patent: WO2013/38206, 2013, A1. Location in patent: Paragraph 10; 11
[4] Journal of the American Chemical Society, 2011, vol. 133, # 7, p. 2076 - 2079
[5] Organic Process Research and Development, 2007, vol. 11, # 3, p. 336 - 340

DHQHS 2(71939-50-9)Related Product Information

• Stanolone
• Hydrochlorothiazide
• Artemisinin
• Podophyllotoxin
• Metronidazole
• Dihydro Artemisinin-d3
• Dihydroartemisinin
• 2-ETHYLHEXANAL DIMETHYL ACETAL
• tert-Butyl hydroperoxide
• tert-Amyl hydroperoxide
• dihydroartemisinin ethyl ether
• Di-tert-butyl peroxide
• alpha-dihydroartemisinin
• Dihydro ArteMisinin-13C,d4
• Diketo aldehyde iMpurity of dihydroarteMisinin
• (3aS,4R,6aS,7R,10R,10aR)-Octahydro-4,7-diMethyl-2H,10H-furo[3,2-i][2]benzopyran-8,10-diol 10-Acetate
• (11S)-Dihydroartemisinic Acid
• 1,1-DI(2-METHYLBUTOXY)ETHANE