artemisic acid Chemical Properties

Melting point:

129-131℃

Boiling point:

373.6±11.0 °C(Predicted)

Density 

1.019

storage temp. 

-20°C Freezer, Under inert atmosphere

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

4.32±0.11(Predicted)

form 

Solid

color 

White to Pale Yellow

InChI

InChI=1/C15H22O2/c1-9-4-6-12-10(2)5-7-13(14(12)8-9)11(3)15(16)17/h8,10,12-14H,3-7H2,1-2H3,(H,16,17)/t10-,12+,13+,14+/s3

InChIKey

PLQMEXSCSAIXGB-OGGOGTMWNA-N

SMILES

[C@]12([H])C=C(CC[C@@]1([H])[C@@H](CC[C@H]2C(=C)C(=O)O)C)C |&1:0,6,8,11,r|

LogP

5.086 (est)

artemisic acid Usage And Synthesis

Chemical Properties

White crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from the Asteraceae plant Artemisia annua.

Uses

Artemisic Acid is a derivative of Artemisinin (A777500), an antimalarial constituent of the tradional Chinese medicinal herb Artemisia annua L., Compositae, which has been known for almost 2000 years as Qinghao. Antimalarial.

Definition

ChEBI: A monocarboxylic acid that is prop-2-enoic acid which is substituted at position 2 by a 4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl group (the 1S,4R,4aS,8aR diastereoisomer). I is a sesquiterpenoid precursor of artemisinin, obtained from sweet wormwood, Artemisia annua.

Synthesis

Jones reagent (1.4 M CrO3 in 2.2 M H2SO4 aqueous solution) was added dropwise to a 1 mL acetone solution containing 0.2 mmol of compound 6 (CAS: 125184-95-4) at 0 °C. The reaction mixture was slowly warmed to room temperature and stirred continuously until complete consumption of Feedstock 6 was confirmed by thin layer chromatography (TLC) monitoring. Upon completion of the reaction, water and dichloromethane (CH2Cl2) were added to the mixture for extraction. The organic layer was separated and washed with distilled water and subsequently dried with anhydrous magnesium sulfate (MgSO4). The solvent was evaporated under reduced pressure to afford the target product 2-((1R,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)acrylic acid in quantitative yield (confirmed by LC/MS). Compound 2 can be further converted to DHAA (3) according to Roth and Acton in Journal of the Chemical Society, Chemical Communications (1989, 24, 1998) or by catalytic hydrogenation (see Example 4).

References

[1] Patent: US2006/270863, 2006, A1. Location in patent: Page/Page column 19

artemisic acid(80286-58-4)Related Product Information

• Artemether
• Artesunate
• artemisic acid
• cis-1,2-divinylcyclohexane
• Dihydro ArteMisinin-13C,d4
• Deoxy Artemisinin
• (3aS,4R,6aS,7R,10R,10aR)-Octahydro-4,7-diMethyl-2H,10H-furo[3,2-i][2]benzopyran-8,10-diol 10-Acetate
• Artemisinin
• DHQHS 2
• Diketo aldehyde iMpurity of dihydroarteMisinin
• (11S)-Dihydroartemisinic Aldehyde
• (11S)-Dihydroartemisinic Acid
• (3R,5aS,6R,8aS,9R,12R,12aR)-Decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-ol
• 9-epi-ArteMisinin
• [[p-(2-methoxyethyl)phenoxy]methyl]oxirane
• anhydrodihydroartemisinin
• DihydroarteMisinic acid
• (11S)-Dihydroartemisinic Alcohol