85031-59-0

Basic information

• Product Name: DihydroarteMisinic acid
• Synonyms: DihydroarteMisinic acid;(alphaR,1R,4R,4aS,8aS)-1,2,3,4,4a,5,6,8a-Octahydro-alpha,4,7-trimethyl-1-naphthaleneacetic acid;Dihydroarteannuic acid;Dihydroqinghao acid
• CAS NO: 85031-59-0
• Molecular Formula: C₁₅H₂₄O₂
• Molecular Weight: 236.34986
• EINECS: -0
• Mol File: 85031-59-0.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 358.8±11.0 °C(Predicted)
• Appearance: /
• 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)
• CAS DataBase Reference: DihydroarteMisinic acid(CAS DataBase Reference)
• NIST Chemistry Reference: DihydroarteMisinic acid(85031-59-0)
• EPA Substance Registry System: DihydroarteMisinic acid(85031-59-0)

Safety Data

• Hazardous Substances Data: 85031-59-0(Hazardous Substances Data)

Usage

Description

DihydroarteMisinic acid is a secondary metabolite derived from Artemisia annua, a plant known for its production of artemisinin. It plays a crucial role in the plant's response to various abiotic stresses, such as cold stress, and is related to the production of artemisinin, a potent antimalarial compound.

Uses

Used in Pharmaceutical Industry:
DihydroarteMisinic acid is used as a precursor in the synthesis of artemisinin and its derivatives, which are potent antimalarial drugs. The overexpression of the NAC transcription factor gene (AaNAC1) in Artemisia annua increases the content of DihydroarteMisinic acid, enhancing the plant's ability to produce artemisinin and its related compounds.
Used in Plant Biotechnology:
DihydroarteMisinic acid is used as a target for genetic engineering and plant breeding efforts aimed at improving the production of artemisinin and related compounds in Artemisia annua. By manipulating the expression of genes like AaNAC1, researchers can potentially increase the yield of these valuable secondary metabolites, contributing to the development of more effective antimalarial treatments.
Used in Stress Resistance Research:
DihydroarteMisinic acid serves as a biomarker for studying the plant's response to abiotic stresses, such as cold stress. Understanding the role of this compound in stress resistance can help researchers develop strategies to improve the resilience of Artemisia annua and other plants to environmental challenges, potentially increasing their productivity and the availability of valuable compounds like artemisinin.

Upstream product

• 80286-58-4 artemisinic acid 
• 917-54-4 methyllithium 
• 103740-02-9 2-(4-methyl-7-oxo-(1α-H),2,3,(4β-H),(4aα-H),5,6,7,8,(8aα-H)-decahydronaphthalen-1-yl)propionic acid 
• 13834-07-6 (1R,3R,4S,8R)-9-hydroxy-p-menthol 
• 7786-67-6 isopulegol 
• 84051-32-1 (2S,5R)-2-((R)-1-(benzyloxy)propan-2-yl)-5-methylcyclohexanone 
• 93913-62-3 3(R)-methyl-6(S)-<1(R)-methyl-2-(phenylmethoxy)ethyl>-2(S)-(3-oxobutyl)cyclohexanone 
• 93913-63-4 1α-Δ⁵-10α-methyl-7β-<2'β-(1'-benzyloxy)-propyl>-decalone-4 
• 84051-31-0 <1R>-5(R)-methyl-2(S)-<1(R)-methyl-2-(phenylmethoxy)ethyl>cyclohexanol 
• 160454-01-3 <4a(S),8a(S)>-octahydro-5(R)-methyl-8(R)-<1(R)-methyl-2-hydroxyethyl>-2(1H)-naphthalenone 
• 125184-93-2 (R)-2-[(1R,4R,4aS,8aS)-4,7-Dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]propanal 
• 92692-39-2 (1R,4R,4aS,8aR)-4,7-dimethyl-1-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene 
• 63968-64-9 C₁₂H₁₃O₂(CH₃)3(O)(OO) 
• 855425-51-3 dihydroartemisinic aldehyde 

Downstream Products

• 63968-64-9 qinghaosu 
• 71816-53-0 (R)-3,6,9-Trimethyl-decahydro-benzo[de]chromen-2-one 
• 141377-47-1 (3R,6R,10aS)-3,6-Dimethyl-9-methylene-decahydro-1,10-dioxa-cyclohepta[de]naphthalen-2-one 
• 78092-22-5 (6R,10aR)-6,9-Dimethyl-3-methylene-3,3a,4,5,6,6a,7,8-octahydro-1-oxa-cyclopenta[d]naphthalen-2-one 
• 82462-58-6 Dihydro-epi-deoxyarteannuin B 
• 63968-64-9 artemisinic acid 
• 105250-95-1 (R)-2-[(1R,2S,3S,4R)-2-Formyl-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid 
• 63968-64-9 C₁₂H₁₃O₂(CH₃)3(O)(OO) 
• 380487-65-0 α-epoxy-dihydroartemisinic acid 
• 104196-16-9 (3R,3a,6R,6aS,10aS)-3a,4,5,6,6a,7,8,8a-octahydro-3,6,9-trimethylnaphtho[8a,1-b]furan-2(3H)-one 
• 207446-83-1 arteanniun H 
• 85031-60-3 4α-hydroperoxy-amorph-5-en-12-oic acid 
• 103775-34-4 (R)-2-[(1R,2S,3S,4R)-2-Formyl-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester 
• 256643-66-0 (1R,2S,3R,6S)-6-Isopropyl-3-methyl-2-(3-oxo-butyl)-cyclohexanecarbaldehyde 

Relevant articles and documents

Preparation method for key intermediate for synthesis of artemisinin compounds

The invention relates to the technical field of organic chemical engineering, in particular to an asymmetric preparation method for synthesizing an artemisinin compound synthesis key intermediate dihydroartemisinic acid. When the intermediate is applied to synthesis of artemisinin compounds, the operation is simple and convenient, the yield and the product purity are improved, and industrial application is easy.

Online Stereochemical Process Monitoring by Molecular Rotational Resonance Spectroscopy

A molecular rotational resonance (MRR) spectrometer designed to monitor the product composition of an asymmetric continuous flow reaction online is presented. The MRR technique is highly sensitive to small changes in molecular structure and, as such, is capable of rapidly quantifying isomers as well as other impurities in a complex mixture, without chromatographic separation or chemometrics. The spectrometer in this study operates by automatically drawing a portion of the reaction solution into a reservoir, volatizing it by heating, and measuring the highly resolved MRR spectra of each of the components of interest in order to determine their relative quantity in the mixture. The reaction under study was the hydrogenation of artemisinic acid, an intermediate step in the semisynthesis of the antimalarial drug artemisinin. Four analytes were characterized in each measurement: the starting material, the product, a diastereomer of the product, and an overreduction byproduct that was not directly quantifiable by either HPLC or NMR methods. The MRR instrument has a measurement cycle time of approximately 17 min for this analysis and can run for several hours without any user interaction.

Preparation method of artemisinin

The invention discloses a preparation method of artemisinin, wherein the preparation method comprise the steps: with artemisinic acid as a starting material, obtaining dihydroartemisinic acid under the hydrogen/metal catalyst action, then oxidizing dihydroartemisinic acid into arteannuic acid dihydrogen peroxide by hydrogen peroxide in the presence of sodium molybdate, and finally acting with oxygen under the catalysis of copper trifluoromethanesulfonate, to obtain the target product artemisinin with high yield. Compared with the prior art, the preparation method has the following advantages:the used reagents are cheap and easy to get, the synthetic route is short, the reaction selectivity is high, the preparation process is environmentally friendly, the operation and post-processing aresimple, the total yield is high, and the preparation method is suitable for industrialized production.