Icaritin
Icaritin structure
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Common Name | Icaritin | ||
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| CAS Number | 118525-40-9 | Molecular Weight | 368.380 | |
| Density | 1.4±0.1 g/cm3 | Boiling Point | 582.0±50.0 °C at 760 mmHg | |
| Molecular Formula | C21H20O6 | Melting Point | 239ºC | |
| MSDS | Chinese USA | Flash Point | 206.7±23.6 °C | |
Use of IcaritinIcaritin(Anhydroicaritin) is a component of Epimedium flavonoid isolated from Herba Epimedii; enhances osteoblastic differentiation of mesenchymal stem cells (MSCs) while it inhibits adipogenic differentiation of MSCs by inhibiting PPAR-g pathway.IC50 value:Target: in vitro: Icaritin was unable to promote proliferation, migration and tube like structure formation by human umbilical vein endothelial cells (HUVECs) in vitro [1]. Icaritin potently inhibited proliferation of K562 cells (IC50 was 8 μM) and primary CML cells (IC50 was 13.4 μM for CML-CP and 18 μM for CML-BC), induced CML cells apoptosis and promoted the erythroid differentiation of K562 cells with time-dependent manner. Furthermore, Icaritin was able to suppress the growth of primary CD34+ leukemia cells (CML) and Imatinib-resistant cells, and to induce apoptosis [2]. icaritin strongly inhibited the growth of breast cancer MDA-MB-453 and MCF7 cells. At concentrations of 2-3 μM, icaritin induced cell cycle arrest at the G(2)/M phase accompanied by a down-regulation of the expression levels of the G(2)/M regulatory proteins such as cyclinB, cdc2 and cdc25C. Icaritin at concentrations of 4-5 μM, however, induced apoptotic cell death characterized by the accumulation of the annexin V- and propidium iodide-positive cells, cleavage of poly ADP-ribose polymerase (PARP) and down-regulation of the Bcl-2 expression [3].in vivo: In mouse leukemia model, Icaritin could prolong lifespan of NOD-SCID nude mice inoculated with K562 cells as effective as Imatinib without suppression of bone marrow. Icaritin could up-regulate phospho-JNK or phospho-C-Jun and down-regulate phospho-ERK, phospho-P-38, Jak-2, phospho-Stat3 and phospho-Akt expression with dose- or time-dependent manner [2]. |
This table lists Chinese names, IUPAC names and various aliases of this chemical substance.
| Name | 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one |
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| Synonym | More Synonyms |
This table contains bioactivity, target information and biological‑assay experimental data of this compound.
| Description | Icaritin(Anhydroicaritin) is a component of Epimedium flavonoid isolated from Herba Epimedii; enhances osteoblastic differentiation of mesenchymal stem cells (MSCs) while it inhibits adipogenic differentiation of MSCs by inhibiting PPAR-g pathway.IC50 value:Target: in vitro: Icaritin was unable to promote proliferation, migration and tube like structure formation by human umbilical vein endothelial cells (HUVECs) in vitro [1]. Icaritin potently inhibited proliferation of K562 cells (IC50 was 8 μM) and primary CML cells (IC50 was 13.4 μM for CML-CP and 18 μM for CML-BC), induced CML cells apoptosis and promoted the erythroid differentiation of K562 cells with time-dependent manner. Furthermore, Icaritin was able to suppress the growth of primary CD34+ leukemia cells (CML) and Imatinib-resistant cells, and to induce apoptosis [2]. icaritin strongly inhibited the growth of breast cancer MDA-MB-453 and MCF7 cells. At concentrations of 2-3 μM, icaritin induced cell cycle arrest at the G(2)/M phase accompanied by a down-regulation of the expression levels of the G(2)/M regulatory proteins such as cyclinB, cdc2 and cdc25C. Icaritin at concentrations of 4-5 μM, however, induced apoptotic cell death characterized by the accumulation of the annexin V- and propidium iodide-positive cells, cleavage of poly ADP-ribose polymerase (PARP) and down-regulation of the Bcl-2 expression [3].in vivo: In mouse leukemia model, Icaritin could prolong lifespan of NOD-SCID nude mice inoculated with K562 cells as effective as Imatinib without suppression of bone marrow. Icaritin could up-regulate phospho-JNK or phospho-C-Jun and down-regulate phospho-ERK, phospho-P-38, Jak-2, phospho-Stat3 and phospho-Akt expression with dose- or time-dependent manner [2]. |
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| Related Catalog | |
| References |
This table shows physicochemical parameters including melting point, boiling point, density, solubility and optical rotation. Missing data is marked as N/A.
| Density | 1.4±0.1 g/cm3 |
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| Boiling Point | 582.0±50.0 °C at 760 mmHg |
| Melting Point | 239ºC |
| Molecular Formula | C21H20O6 |
| Molecular Weight | 368.380 |
| Flash Point | 206.7±23.6 °C |
| Exact Mass | 368.125977 |
| PSA | 100.13000 |
| LogP | 4.84 |
| Appearance of Characters | light yellow to dark yellow |
| Vapour Pressure | 0.0±1.7 mmHg at 25°C |
| Index of Refraction | 1.657 |
| InChIKey | TUUXBSASAQJECY-UHFFFAOYSA-N |
| SMILES | COc1ccc(-c2oc3c(CC=C(C)C)c(O)cc(O)c3c(=O)c2O)cc1 |
| Storage condition | 2-8°C |
| Water Solubility | DMSO: soluble5mg/mL, clear (warmed) |
This table provides MSDS information including hazard classification, first‑aid, fire‑fighting, spill handling, operation and storage instructions.
This table covers safety warnings, protective measures, incompatible substances and disposal guidelines for this compound.
| RIDADR | NONH for all modes of transport |
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| RTECS | DJ3100870 |
This table presents publicly reported synthetic routes, reaction conditions, reactants and product information of the compound.
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~97%
Icaritin CAS#:118525-40-9 |
| Literature: Dell'Agli, Mario; Galli, Germana V.; Dal Cero, Esther; Belluti, Federica; Matera, Riccardo; Zironi, Elisa; Pagliuca, Giampiero; Bosisio, Enrica Journal of Natural Products, 2008 , vol. 71, # 9 p. 1513 - 1517 |
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~%
Icaritin CAS#:118525-40-9 |
| Literature: Heterocycles, , vol. 26, # 4 p. 935 - 938 |
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~%
Icaritin CAS#:118525-40-9 |
| Literature: Heterocycles, , vol. 26, # 4 p. 935 - 938 |
This table lists upstream starting materials and downstream derivative products related to this chemical.
| Precursor 3 | |
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| DownStream 1 | |
CAS#:28610-31-3This table lists relevant public references with title, journal and publication metadata for this compound.
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Icaritin ameliorates carbon tetrachloride-induced acute liver injury mainly because of the antioxidative function through estrogen-like effects.
In Vitro Cell. Dev. Biol. Anim. 50(10) , 899-908, (2014) To investigate the effects of icaritin, an active ingredient extracted from Epimedium Sagittatum (Sieb. et Zucc.), on CCl4-induced liver injury and its possible mechanisms. Hepatocytes isolated from S... |
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Icaritin induces lytic cytotoxicity in extranodal NK/T-cell lymphoma.
J. Exp. Clin. Cancer Res 34 , 17, (2015) Extranodal NK/T-cell lymphoma (ENKL) is an aggressive hematological malignancy associated with Epstein-Barr virus (EBV) infection. It is often resistant to conventional chemotherapy and has a poor pro... |
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Icaritin, an exogenous phytomolecule, enhances osteogenesis but not angiogenesis--an in vitro efficacy study.
PLoS ONE 7 , e41264, (2012) We found that Icaritin, an intestinal metabolite of Epimedium-derived flavonoids (EF) enhanced osteoblastic differentiation of mesenchymal stem cells (MSCs) only under osteogenic induction conditions.... |
This table contains target information, in‑vitro & in‑vivo assay data for this compound.
This table collects all English aliases, systematic names and CAS‑related synonyms of the compound.
| 3,5,7-Trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one |
| Icaritin |
| 3,5,7-Trihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-chromen-4-one |
| BIDD:ER0021 |
| 3,7-dihydroxy-8-prenyl-4'-methoxychrysin |
| Anhydroicaritin |
This section contains frequently‑asked‑questions about this compound, including basic parameters, properties, storage conditions and corresponding answers.
| Q: What are the upstream materials of 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one? |
| A: Related upstream materials(CAS) of 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one: 489-32-7;110623-72-8;118525-35-2. |
| Q: What are the downstream products of 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one? |
| A: Related downstream products(CAS) of 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one: 28610-31-3. |
| Q: What are the storage conditions for 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one? |
| A: Storage conditions for 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one: 2-8°C. |
| Q: How is the water solubility of 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one? |
| A: Water solubility of 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one: DMSO: soluble5mg/mL, clear (warmed). |
| Q: What is the CAS number of 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one? |
| A: CAS number of 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one is 118525-40-9. |
| Q: What is the molecular formula of 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one? |
| A: Molecular formula of 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one is C21H20O6. |
| Q: What is the LogP of 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one? |
| A: LogP of 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one is 4.84. |
| Q: What is the physical appearance of 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one? |
| A: 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one appears as light yellow to dark yellow. |
| Q: What is the English name of 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one? |
| A: The English name of 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one is 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one. |
| Q: What is the melting point of 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one? |
| A: Melting point of 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one is 239ºC. |
This table lists manufacturers and suppliers of this compound, including vendor names and product supply reference information.
| Shanghai Nianxing Industrial Co., Ltd |
| BioBioPha |
| naturewill |
| Henan Tianfu Chemical Co., Ltd. |