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Artemisic acid

Alias: Arteannuic acid Artemisinic acid Qing Hao acid
Cat No.:V29259 Purity: ≥98%
Artemisic acid(Qing Hao acid) is a naturally occurring amorphane sesquiterpene found inArtemisia annua L.
Artemisic acid
Artemisic acid Chemical Structure CAS No.: 80286-58-4
Product category: New12
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Artemisic acid (Qing Hao acid) is a naturally occurring amorphane sesquiterpene found in Artemisia annua L., with various pharmacological activity like antimalarial activity, antipyretic effect, antibacterial activity, anti-tumor activity, allelopathy effect and anti-adipogenesis effects.
Artemisic acid (CAS 80286-58-4), also known as artemisinic acid or Qing Hao acid, is a naturally occurring amorphane-type sesquiterpene monocarboxylic acid predominantly isolated from Artemisia annua L. (sweet wormwood). It is recognized as the immediate biogenetic precursor to the endoperoxide-containing antimalarial drug artemisinin. Beyond its established role in semi-synthesis, this compound has been identified as a bioactive molecule with distinct pharmacological activities, including antimalarial, anti-tumor, antipyretic, antibacterial, allelopathy, and anti-adipogenesis effects. Artemisic acid serves a dual purpose: a cost-effective starting material for artemisinin synthesis (with 8–10× higher natural abundance than artemisinin) and a differentiated bioactive probe for various research applications.
Biological Activity I Assay Protocols (From Reference)
Targets
The primary therapeutic target of Artemisic acid is the malaria parasite Plasmodium species, against which it disrupts cellular function. As a precursor to artemisinin, its antimalarial mechanism is ultimately linked to the endoperoxide bridge formed during synthesis, which generates reactive oxygen species that damage the parasite. Beyond antimalarial applications, it exhibits antibacterial activity, anti-adipogenic effects through reduced expression of C/EBPδ and PPARγ, and anti-mycobacterial activity. Artemisinic acid also decreases triglyceride levels and glycerol-3-phosphate dehydrogenase (GPDH) activity in human adipose tissue-derived mesenchymal stem cells (hAMSCs).
ln Vitro
In vitro, Artemisic acid demonstrates antibacterial activity and is active against different bacteria and certain fungal species. It exhibits anti-adipogenic effects in hAMSCs at concentrations of 50-400 µM, decreasing triglyceride levels and GPDH activity in a dose-dependent manner, and inhibits adipocyte differentiation at 200 µM. It also shows anti-mycobacterial potency with a reported MIC of 250 µg/mL, which is superior to artemisinin's 1000 µg/mL. Antimalarial activity has been reported with an IC50 of approximately 62-78 µM, though an IC50 greater than 175 µM has also been noted in some studies.
ln Vivo
In vivo, Artemisic acid has demonstrated antipyretic effects and serves as the biosynthetic precursor to artemisinin, which is clinically used as an antimalarial agent. As a precursor, its in vivo efficacy against malaria is realized through conversion to artemisinin or related derivatives. The compound also shows anti-adipogenesis effects in vivo through modulation of adipocyte differentiation pathways. However, detailed in vivo pharmacokinetic and pharmacodynamic data for Artemisic acid itself, independent of its role as a precursor, remain limited in publicly available literature.
Enzyme Assay
For cell-free enzyme assays involving Artemisic acid, typical protocols include enzyme inhibition studies using purified targets such as HMG-CoA reductase or other metabolic enzymes. The compound's role as a precursor in artemisinin synthesis can be studied using in vitro enzymatic conversion assays with cytochrome P450 enzymes that catalyze the oxidation of artemisinic acid to artemisinin. Antimicrobial activity can be assessed via standard broth microdilution methods to determine minimum inhibitory concentration (MIC) values against bacterial or fungal strains.
Cell Assay
In vitro cellular activity is assessed using standard cell lines such as hAMSCs for anti-adipogenic studies. Cells are treated with serial dilutions of Artemisic acid (e.g., 50-400 µM) and endpoints include triglyceride level measurement, glycerol-3-phosphate dehydrogenase (GPDH) activity assays, and analysis of adipocyte differentiation markers such as C/EBPδ and PPARγ expression via Western blot or qPCR. Cytotoxicity and antiproliferative effects can be evaluated using MTT or SRB assays in cancer cell lines to assess anti-tumor activity.
Animal Protocol
In vivo efficacy is evaluated in animal models of malaria (e.g., Plasmodium-infected mice) or inflammation. As a precursor to artemisinin, Artemisic acid can be administered via oral gavage or intraperitoneal injection, and endpoints include parasitemia reduction, survival rate, and inflammatory biomarker analysis. For anti-adipogenic studies, rodent models of obesity or metabolic syndrome may be used, with endpoints including body weight, adipose tissue mass, and serum lipid profiles.
ADME/Pharmacokinetics
DMSO solubility: 60-100 mg/mL; in vivo formulation: 10% DMSO + 40% PEG300 + 5% Tween-80 + 45% saline (≥2.5 mg/mL). Molecular weight: 234.33 g/mol; molecular formula: C15H22O2. Density: 1.5±0.1 g/cm³. Powder stable at -20°C for 3 years, 4°C for 2 years; in solvent at -80°C for 6 months, -20°C for 1 month.
Toxicity/Toxicokinetics
No detailed toxicity data is publicly available. As a natural sesquiterpene from Artemisia annua, it is generally considered to have low toxicity, but standard safety pharmacology and toxicology studies (e.g., acute toxicity in rodents, Ames test for genotoxicity, hERG assay for cardiotoxicity) would be required for drug development. Some studies indicate that concentrations exceeding 175 µM may be required to observe significant effects.
References
Artemisinic acid: A promising molecule potentially suitable for the semi-synthesis of artemisinin. RSC Adv. 2013.
Additional Infomation
(+)-Artemisinic acid is a monocarboxylic acid with the structure of a 2-enoic acid, substituted at the 2-position with a 4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphth-1-yl group (1S,4R,4aS,8aR diastereomers). It is the sesquiterpene precursor of artemisinin, extracted from Artemisia annua. It is a metabolite. It is a monocarboxylic acid, a carbon-bicyclic compound, a sesquiterpene, and a member of the octahydronaphthyl group. Functionally, it is related to (+)-artemisinol. It is the conjugate acid of (+)-artemisinic acid ester. Artemisinic acid has been reported to exist in Artemisia annua, Artemisia carvifolia, and other organisms with relevant data.
Artemisic acid is a research-grade compound, not approved for therapeutic use. It is primarily used as a reference standard, a starting material for the semi-synthesis of artemisinin and related derivatives, and a subject of investigation for its intrinsic biological properties. No clinical trials or FDA approval have been reported for Artemisic acid itself; it remains in preclinical research stages. Its mechanism includes antimalarial activity through disruption of Plasmodium cellular function and anti-adipogenic effects via regulation of C/EBPδ and PPARγ expression.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C₁₅H₂₂O₂
Molecular Weight
234.33
Exact Mass
234.161
CAS #
80286-58-4
PubChem CID
10922465
Appearance
White to off-white solid powder
Density
1.0±0.1 g/cm3
Boiling Point
373.6±11.0 °C at 760 mmHg
Melting Point
129-131℃
Flash Point
273.3±10.2 °C
Vapour Pressure
0.0±1.8 mmHg at 25°C
Index of Refraction
1.505
LogP
5.11
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
2
Heavy Atom Count
17
Complexity
367
Defined Atom Stereocenter Count
4
SMILES
C[C@@H]1CC[C@H]([C@@H]2[C@H]1CCC(=C2)C)C(=C)C(=O)O
InChi Key
PLQMEXSCSAIXGB-SAXRGWBVSA-N
InChi Code
InChI=1S/C15H22O2/c1-9-4-6-12-10(2)5-7-13(14(12)8-9)11(3)15(16)17/h8,10,12-14H,3-7H2,1-2H3,(H,16,17)/t10-,12+,13+,14+/m1/s1
Chemical Name
2-[(1R,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]prop-2-enoic acid
Synonyms
Arteannuic acid Artemisinic acid Qing Hao acid
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~426.75 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 0.83 mg/mL (3.54 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 8.3 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 0.83 mg/mL (3.54 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 8.3 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 0.83 mg/mL (3.54 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 8.3 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.2675 mL 21.3374 mL 42.6749 mL
5 mM 0.8535 mL 4.2675 mL 8.5350 mL
10 mM 0.4267 mL 2.1337 mL 4.2675 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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