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for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at 2-8°C,Protected from light,Desiccated Ships Wet ice Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Girinimbine (Girinimbin) is a carbazole alkaloid with a variety of biological effects. Girinimbine can induce apoptosis , and has antitrypanosomal, antiplatelet activity, antibacterial activity, anti-inflammatory, antioxidant and antitumor activities .
In Vitro
Girinimbine (1-400 µM; 24-72 h) decreases the viability of HepG2 cells in 24, 48 and 72 h with IC 50 values of 61 µM, 56 µM, and 40 µM respectively. Girinimbine (10-100 µM; 24-48 h) increase of LDH leakage in both concentration- and time-dependent manner in HepG2 cells. Girinimbine (56 µM; 24-48 h) treatment results in DNA fragmentation and elevates levels of caspase-3 in HepG2 cells.\nHepG2 cells. Girinimbine (56 µM; 12-48 h) treatment also displays a time-dependent accumulation of the Sub-G0/G1 peak (hypodiploid) and caused G0/G1-phase arrest. Girinimbine shows a potent antitrypanosomal activitywith an IC 50 value of 10.16 µg/mL. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Cell Viability AssayCell Line: HepG2 cells Concentration: 1 µM, 10 µM, 50 µM, 100 µM, 200 µM Incubation Time: 24 h, 48 h and 72 h Result: Inhibited the proliferation of HepG2 cells in vitro in a dose- and time-dependent manner. Apoptosis AnalysisCell Line: HepG2 cells Concentration: 56 µM Incubation Time: 24 h, 48 h Result: Showed typical morphological features of apoptosis. Cell Cycle AnalysisCell Line: HepG2 cells Concentration: 56 µM Incubation Time: 12 h, 24 h, 48 h Result: Induced G0/G1-phase arrest in HepG2 cells.
In Vivo
Girinimbine (10-100 mg/kg; orally gavage; once) pretreatment helps limit total leukocyte migration, and reduced pro-inflammatory cytokine (IL-1β, TNF-α) levels in the peritoneal fluid. In vivo in zebrafish embryos, Girinimbine (20 μg/mL; 24 hours) shows significant distribution of apoptotic cells in embryos. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Male ICR mice (25-35 g) treated with carrageenanDosage: 10 mg/kg, 30 mg/kg, and 100 mg/kg Administration: Orally gavage; once Result: Helped limit total leukocyte migration, and reduced pro-inflammatory cytokine levels in the peritoneal fluid.
Form:Solid
| Canonical Smiles | CC1=CC2=C(C3=C1OC(C=C3)(C)C)NC4=CC=CC=C42 |
|---|---|
| IUPAC Name | 3,3,5-trimethyl-11H-pyrano[3,2-a]carbazole |
| InChIKey | GAEQWKVGMHUUKO-UHFFFAOYSA-N |
| INCHI | 1S/C18H17NO/c1-11-10-14-12-6-4-5-7-15(12)19-16(14)13-8-9-18(2,3)20-17(11)13/h4-10,19H,1-3H3 |
| Isomeric SMILES | CC1=CC2=C(C3=C1OC(C=C3)(C)C)NC4=CC=CC=C42 |
| Alternate CAS | 23095-44-5 |
| PubChem CID | 96943 |
| NSC Number | 94932 |
| MeSH Entry Terms | girinimbin;girinimbine |
| Molecular Weight | 263.33 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organoheterocyclic compounds |
| Class | Indoles and derivatives |
| Subclass | Carbazoles |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Carbazoles |
| Alternative Parents | 2,2-dimethyl-1-benzopyrans Indoles Alkyl aryl ethers Benzenoids Pyrroles Heteroaromatic compounds Oxacyclic compounds Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Hydrocarbon derivatives |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Carbazole - 2,2-dimethyl-1-benzopyran - Benzopyran - 1-benzopyran - Indole - Alkyl aryl ether - Benzenoid - Heteroaromatic compound - Pyrrole - Ether - Oxacycle - Azacycle - Organonitrogen compound - Hydrocarbon derivative - Organic nitrogen compound - Organopnictogen compound - Organooxygen compound - Organic oxygen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as carbazoles. These are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. |
| External Descriptors | carbazoles |
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| Molecular Weight | 263.300 g/mol |
|---|---|
| XLogP3 | 4.700 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Exact Mass | 263.131 Da |
| Monoisotopic Mass | 263.131 Da |
| Topological Polar Surface Area | 25.000 Ų |
| Heavy Atom Count | 20 |
| Formal Charge | 0 |
| Complexity | 416.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |