DihydroarteMisinic acid
- Product Name
- DihydroarteMisinic acid
- CAS No.
- 85031-59-0
- Chemical Name
- DihydroarteMisinic acid
- Synonyms
- product/154911;Dihydroqinghao acid;Dihydroarteannuic acid;Dihydro-Artmisinic Acid;DihydroarteMisinic 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)-;(R)-2-((1R,4R,4aS,8aS)-4,7-Dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)propanoic acid;2-(4,7-dimethyl-(1α-H),2,3,(4β-H),(4aα-H),5,6,(8aα-H)-octahydronaphthalen-1-yl)propionic acid
- CBNumber
- CB82721037
- Molecular Formula
- C15H24O2
- Formula Weight
- 236.35
- MOL File
- 85031-59-0.mol
DihydroarteMisinic acid Property
- 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|
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H319Causes serious eye irritation
- Precautionary statements
-
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- D6147
- Product name
- Dihydroartemisinic acid
- Purity
- min. 98.0 %
- Packaging
- 200MG
- Price
- $104
- Updated
- 2025/07/31
- Product number
- D6147
- Product name
- Dihydroartemisinic acid
- Purity
- min. 98.0 %
- Packaging
- 1G
- Price
- $312
- Updated
- 2025/07/31
- Product number
- 25142
- Product name
- Dihydroartemisinic Acid
- Purity
- ≥98%
- Packaging
- 1mg
- Price
- $32
- Updated
- 2024/03/01
- Product number
- 25142
- Product name
- Dihydroartemisinic Acid
- Purity
- ≥98%
- Packaging
- 5mg
- Price
- $139
- Updated
- 2024/03/01
- Product number
- 25142
- Product name
- Dihydroartemisinic Acid
- Purity
- ≥98%
- Packaging
- 10mg
- Price
- $243
- Updated
- 2024/03/01
DihydroarteMisinic acid Chemical Properties,Usage,Production
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
80286-58-4
85031-59-0
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 Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from DihydroarteMisinic acid manufacturers
- Product
- 2-(4,7-dimethyl-(1α-H),2,3,(4β-H),(4aα-H),5,6,(8aα-H)-octahydronaphthalen-1-yl)propionic acid 85031-59-0
- Price
- US $9.80/KG
- Min. Order
- 1KG
- Purity
- ≥98%
- Supply Ability
- 20 tons
- Release date
- 2020-01-09