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Chrysoobtusin

Cat No.:V58039 Purity: ≥98%
Chrysoobtusin is an anthraquinone analogue extracted from Cassia seeds.
Chrysoobtusin
Chrysoobtusin Chemical Structure CAS No.: 70588-06-6
Product category: Phenols
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
10mg
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Product Description
Chrysoobtusin is an anthraquinone analogue extracted from Cassia seeds. Semen Cassiae has long been used to protect the liver, improve eyesight, and relieve constipation.
Chrysoobtusin is a naturally occurring monohydroxyanthraquinone characterized by a planar anthraquinone core substituted with a methyl group and four methoxy groups. It is isolated from the seeds of Cassia tora and Cassia obtusifolia (Semen Cassiae), a traditional Chinese medicinal herb used for liver protection, vision improvement, and constipation relief.
Biological Activity I Assay Protocols (From Reference)
Targets
Chrysoobtusin targets multiple enzymes: it acts as a moderate thrombin inhibitor with an IC50 of 20.37 µM and serves as a negative control for aldose reductase (no significant inhibition vs. aurantio-obtusin IC50=13.6 µM). It also exhibits distinct selectivity for BSA versus insulin glycation, indicating multiple protein-targeting mechanisms.
ln Vitro
Chrysoobtusin demonstrates anti-glycation activity by inhibiting the formation of advanced glycation end-products (AGEs), which are implicated in diabetes complications. It shows antioxidant properties through its anthraquinone structure. It exhibits moderate thrombin inhibition (IC50=20.37 µM) and antimutagenic activity against aflatoxin B1 in Salmonella typhimurium assays.
ln Vivo
In vivo studies indicate that Chrysoobtusin metabolites are excreted in urine, suggesting systemic absorption and metabolism. The compound is traditionally used for hepatoprotective effects, and animal studies support its liver-protective properties. It exhibits anti-inflammatory effects in models of arthritis and asthma, demonstrating potential therapeutic benefits for inflammatory diseases.
Enzyme Assay
In vitro enzyme assays for Chrysoobtusin: aldose reductase inhibition is measured using rat lens aldose reductase with DL-glyceraldehyde as substrate, monitoring NADPH oxidation at 340 nm. Thrombin inhibition is assessed using chromogenic substrate S-2238, measuring absorbance at 405 nm. Glycation inhibition is evaluated using BSA or insulin with glucose, monitoring AGE fluorescence at excitation/emission of 370/440 nm.
Cell Assay
Cell-based assays for Chrysoobtusin: hepatocytes (e.g., HepG2 cells) are cultured in DMEM with 10% FBS and treated with Chrysoobtusin (0-100 µM) for 24-48 hours. Cell viability is measured by MTT assay. Anti-inflammatory activity is assessed in LPS-stimulated macrophages by measuring TNF-α and IL-6 via ELISA. Antimutagenic activity is evaluated using Salmonella typhimurium strains in the Ames test.
Animal Protocol
In vivo animal studies for Chrysoobtusin: rodent models are used to evaluate hepatoprotective effects. Animals are administered Chrysoobtusin orally at doses of 10-50 mg/kg for 7-14 days, followed by induction of liver injury using CCl4 or paracetamol. Serum markers (ALT, AST, ALP) and hepatic oxidative stress parameters (MDA, SOD, CAT) are measured to assess protective effects.
ADME/Pharmacokinetics
Pharmacokinetic studies show that Chrysoobtusin metabolites are excreted in urine, indicating systemic absorption. The compound likely undergoes phase I and phase II metabolism in the liver, including demethylation and glucuronidation. Oral bioavailability may be moderate due to its anthraquinone structure. The elimination half-life and volume of distribution require further investigation.
Toxicity/Toxicokinetics
Comprehensive toxicity data for Chrysoobtusin are limited. As an anthraquinone derivative from a traditional medicinal plant, it is generally considered safe at moderate doses. However, some anthraquinones have been associated with hepatotoxicity and genotoxicity at high doses. Long-term safety studies and clinical trials are lacking; the compound has not been approved for therapeutic use.
References

[1]. Simultaneous determination of aurantio-obtusin, chrysoobtusin, obtusin and 1-desmethylobtusin in rat plasma by UHPLC-MS/MS. Biomed Chromatogr. 2014;28(3):369-374.

[2]. Nine components pharmacokinetic study of rat plasma after oral administration raw and prepared Semen Cassiae in normal and acute liver injury rats. J Sep Sci. 2019;42(14):2341-2350.

Additional Infomation
Chrysoobtusin is a monohydroxyanthraquinone. Chrysoobtusin has been reported in senna leaves and senna leaf extract, and available data are available.
Chrysoobtusin is a research-grade compound used for pharmacological studies, particularly in diabetes, inflammation, and hepatoprotection research. Its mechanism involves inhibition of glycation and modulation of enzyme activities. The compound is available as a reference standard for analytical applications. No clinical trials or FDA approvals have been reported for Chrysoobtusin.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C19H18O7
Molecular Weight
358.34
Exact Mass
358.105
CAS #
70588-06-6
PubChem CID
155381
Appearance
White to yellow solid
Density
1.3±0.1 g/cm3
Boiling Point
586.2±50.0 °C at 760 mmHg
Melting Point
215-216 ºC
Flash Point
212.4±23.6 °C
Vapour Pressure
0.0±1.7 mmHg at 25°C
Index of Refraction
1.598
LogP
3.36
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
4
Heavy Atom Count
26
Complexity
550
Defined Atom Stereocenter Count
0
SMILES
O=C1C2=C(C=C(OC)C(OC)=C2OC)C(C3=CC(C)=C(O)C(OC)=C13)=O
InChi Key
ZMDXTRSTKHTSCE-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H18O7/c1-8-6-9-12(18(25-4)14(8)20)16(22)13-10(15(9)21)7-11(23-2)17(24-3)19(13)26-5/h6-7,20H,1-5H3
Chemical Name
2-hydroxy-1,6,7,8-tetramethoxy-3-methylanthracene-9,10-dione
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: This product requires protection from light (avoid light exposure) during transportation and storage.
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: 20 mg/mL (55.81 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 0.71 mg/mL (1.98 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 7.1 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.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.7906 mL 13.9532 mL 27.9065 mL
5 mM 0.5581 mL 2.7906 mL 5.5813 mL
10 mM 0.2791 mL 1.3953 mL 2.7906 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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g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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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