DihydroarteMisinic acid Chemical Properties

Melting point:

135-137°C

Boiling point:

358.8±11.0 °C(Predicted)

Density 

0.999±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Slightly)

pka

4.65±0.10(Predicted)

form 

Solid

color 

White to Off-White

InChI

InChI=1/C15H24O2/c1-9-4-6-12-10(2)5-7-13(14(12)8-9)11(3)15(16)17/h8,10-14H,4-7H2,1-3H3,(H,16,17)/t10-,11-,12+,13+,14+/s3

InChIKey

JYGAZEJXUVDYHI-LAFUBWOENA-N

SMILES

C[C@@H](C(=O)O)[C@H]1[C@]2([H])[C@](CCC(=C2)C)([H])[C@H](C)CC1 |&1:1,5,6,8,15,r|

DihydroarteMisinic acid Usage And Synthesis

Uses

Dihydroartemisinic Acid is produced and its content is increased in Artemisia annua when NAC transcription factor gene (AaNAC1) is overexpressed, which play an important role in response to various abiotic stresses. Also, it is related secondary metabolites of artemisinin which increases in A. annua under cold stress.

Definition

ChEBI: Dihydroartemisinic acid is a monocarboxylic acid that is propanoic acid substituted at position 2 by a (1S,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl group. It is a sesquiterpenoid precursor of the antimalarial drug, artemisinin. It has a role as a plant metabolite. It is a carbobicyclic compound, a monocarboxylic acid, a member of octahydronaphthalenes and a sesquiterpenoid. It is a conjugate acid of a dihydroartemisinate.

Synthesis

The general procedure for the synthesis of (R)-2-((1R,4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)propionic acid from 2-((1R,4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)propanoic acid was as follows. 100 g (0.43 mol) of 2-((1R,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)acrylic acid was dissolved in 800 mL of chloroform. The reaction was carried out overnight at room temperature with 1.5 g of palladium carbon as catalyst under a hydrogen pressure of 1 bar. After completion of the reaction, the reaction mixture was filtered through diatomaceous earth and the filter cake was washed with chloroform. Finally, the solvent was recovered by distillation under reduced pressure to afford 99 g (0.42 mol) of the solid product (R)-2-((1R,4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)propionic acid in 98% yield.

IC 50

Plasmodium

References

[1] Journal of Organic Chemistry, 1986, vol. 51, # 26, p. 5417 - 5419
[2] Organic Letters, 2016, vol. 18, # 9, p. 2122 - 2125
[3] Patent: CN107793429, 2018, A. Location in patent: Sheet 0022; 0023; 0027; 0031
[4] Patent: WO2011/30223, 2011, A2. Location in patent: Page/Page column 17; 18
[5] Patent: EP2660234, 2013, A1. Location in patent: Paragraph 0039

DihydroarteMisinic acid(85031-59-0)Related Product Information

• (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
• Dihydro ArteMisinin-13C,d4
• Deoxy Artemisinin
• 9-epi-ArteMisinin
• (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
• (11S)-Dihydroartemisinic Acid
• [[p-(2-methoxyethyl)phenoxy]methyl]oxirane
• artemisic acid
• anhydrodihydroartemisinin
• (11S)-Dihydroartemisinic Alcohol
• Artemisinin impurity 4
• DIHYDRO-ARTEMISININ GLUCURONIDE
• Artemisinin impurity 2
• Arteannuin H