ChemicalBook > CAS DataBase List > DihydroarteMisinic acid

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

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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|

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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.

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N-Bromosuccinimide Price

TCI Chemical

Product number: D6147
Product name: Dihydroartemisinic acid
Purity: min. 98.0 %
Packaging: 200MG
Price: $104
Updated: 2025/07/31

TCI Chemical

Product number: D6147
Product name: Dihydroartemisinic acid
Purity: min. 98.0 %
Packaging: 1G
Price: $312
Updated: 2025/07/31

Cayman Chemical

Product number: 25142
Product name: Dihydroartemisinic Acid
Purity: ≥98%
Packaging: 1mg
Price: $32
Updated: 2024/03/01

Cayman Chemical

Product number: 25142
Product name: Dihydroartemisinic Acid
Purity: ≥98%
Packaging: 5mg
Price: $139
Updated: 2024/03/01

Cayman Chemical

Product number: 25142
Product name: Dihydroartemisinic Acid
Purity: ≥98%
Packaging: 10mg
Price: $243
Updated: 2024/03/01

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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

Career Henan Chemical Co

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

85031-59-0, DihydroarteMisinic acidRelated Search:

(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

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

(2R)-dihydroartemisinic acid

2-(4,7-dimethyl-(1α-H),2,3,(4β-H),(4aα-H),5,6,(8aα-H)-octahydronaphthalen-1-yl)propionic acid

Dihydroqinghao acid

Dihydro-Artmisinic Acid

product/154911

1-Naphthaleneacetic acid, 1,2,3,4,4a,5,6,8a-octahydro-α,4,7-trimethyl-, (αR,1R,4R,4aS,8aS)-

DihydroarteMisinic acid USP/EP/BP

(R)-2-((1R,4R,4aS,8aS)-4,7-Dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)propanoic acid

85031-59-0