| Identification | Back Directory | [Name]
DihydroarteMisinic acid | [CAS]
85031-59-0 | [Synonyms]
product/154911
Dihydroqinghao acid
Dihydroarteannuic acid
DihydroarteMisinic acid
Dihydro-Artmisinic Acid
(2R)-dihydroartemisinic acid
DihydroarteMisinic acid USP/EP/BP
1-Naphthaleneacetic acid, 1,2,3,4,4a,5,6,8a-octahydro-α,4,7-trimethyl-, (αR,1R,4R,4aS,8aS)-
2-(4,7-dimethyl-(1α-H),2,3,(4β-H),(4aα-H),5,6,(8aα-H)-octahydronaphthalen-1-yl)propionic acid
(alphaR,1R,4R,4aS,8aS)-1,2,3,4,4a,5,6,8a-Octahydro-alpha,4,7-trimethyl-1-naphthaleneacetic acid | [EINECS(EC#)]
813-723-9 | [Molecular Formula]
C15H24O2 | [MDL Number]
MFCD16876168 | [MOL File]
85031-59-0.mol | [Molecular Weight]
236.35 |
| Chemical Properties | Back Directory | [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) | [form ]
Solid | [pka]
4.65±0.10(Predicted) | [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| |
| Hazard Information | Back Directory | [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 |
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