Dihydroartemisinic acid

Base Information

• Chemical Name: Dihydroartemisinic acid
• CAS No.: 85031-59-0
• Molecular Formula: C₁₅H₂₄O₂
• Molecular Weight: 236.354
• European Community (EC) Number: 813-723-9
• Nikkaji Number: J1.110.895D
• Wikidata: Q76416465
• ChEMBL ID: CHEMBL5192325
• Mol file: 85031-59-0.mol

Synonyms:dihydroartemisinic acid

Chemical Property of Dihydroartemisinic acid

Chemical Property:

• Boiling Point: 358.8±11.0 °C(Predicted)
• PKA: 4.65±0.10(Predicted)
• PSA: 37.30000
• Density: 0.999±0.06 g/cm3(Predicted)
• LogP: 3.72570
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), DMSO (Slightly)
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 236.177630004
• Heavy Atom Count: 17
• Complexity: 332

Purity/Quality:

97% ^*data from raw suppliers

Dihydroartemisinicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(C2C1CCC(=C2)C)C(C)C(=O)O
• Isomeric SMILES: C[C@@H]1CC[C@H]([C@@H]2[C@H]1CCC(=C2)C)[C@@H](C)C(=O)O
• 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.

Technology Process of Dihydroartemisinic acid

There total 16 articles about Dihydroartemisinic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

artemisinic acid (80286-58-4) → dihydroartemisinic acid (85031-59-0,110715-68-9,126643-10-5)

Guidance literature:

With lithium borohydride; nickel dichloride; In methanol; for 2h; Ambient temperature;

DOI:10.1021/jo00376a070

Reference yield: 79.9%

(R)-2-[(1R,4R,4aS,8aS)-4,7-Dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]propanal (125184-93-2) → dihydroartemisinic acid (85031-59-0,110715-68-9,126643-10-5)

Guidance literature:

With disodium hydrogenphosphate; In dimethyl sulfoxide; at 20 ℃; for 2h;

DOI:10.1073/pnas.1110740109

Reference yield: 33.0%

(R)-2-((1R,4R,4aS)-7-Hydroxy-4,7-dimethyl-decahydro-naphthalen-1-yl)-propionic acid → dihydroartemisinic acid (85031-59-0,110715-68-9,126643-10-5) + 2-(4,7-dimethyl-(1α-H),2,3,(4β-H),(4aα-H),5,8,(8aα-H)-octahydronaphthalen-1-yl)propionic acid + 2-(4,7-dimethyl-(1α-H),2,3,(4β-H),(4aα-H),5,8,(8aβ-H)-octahydronaphthalen-1-yl)propionic acid + 2-(4,7-dimethyl-(1α-H),2,3,(4β-H),(4aα-H),5,6,(8aβ-H)-octahydronaphthalen-1-yl)propionic acid

Guidance literature:

With silica gel; copper(II) sulfate; In 1,1,2,2-tetrachloroethylene; Heating;

DOI:10.1016/j.tet.2003.11.069

upstream raw materials:

artemisinic acid

methyllithium

2-(4-methyl-7-oxo-(1α-H),2,3,(4β-H),(4aα-H),5,6,7,8,(8aα-H)-decahydronaphthalen-1-yl)propionic acid

(1R,3R,4S,8R)-9-hydroxy-p-menthol

Downstream raw materials:

qinghaosu

(R)-2-[(1R,2S,3S,4R)-2-Formyl-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid

C₁₂H₁₃O₂(CH₃)3(O)(OO)

(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