ginkgetin
ginkgetin structure
|
Common Name | ginkgetin | ||
|---|---|---|---|---|
| CAS Number | 481-46-9 | Molecular Weight | 566.511 | |
| Density | 1.5±0.1 g/cm3 | Boiling Point | 863.7±65.0 °C at 760 mmHg | |
| Molecular Formula | C32H22O10 | Melting Point | 336ºC | |
| MSDS | N/A | Flash Point | 287.2±27.8 °C | |
Use of ginkgetinGinkgetin is a natural biflavonoid isolated from leaves of Ginkgo biloba L; effects of anti-inflammation and anticancer have been reported.IC50 value:Target:in vitro: Ginkgetin inhibits COX-2 dependent phases of prostaglandin D(2) (PGD(2)) generation in bone marrow-derived mast cells (BMMC) in a concentration-dependent manner with IC(50) values of 0.75 microM. Ginkgetin consistently inhibited the production of leukotriene C(4) (LTC(4)) in a dose dependent manner, with an IC(50) value of 0.33 microM. Ginkgetin also inhibited degranulation reaction in a dose dependent manner, with an IC(50) value of 6.52 microM [1]. Ginkgetin inhibited both inducible and constitutively activated STAT3 and blocked the nuclear translocation of p-STAT3 in DU-145 prostate cancer cells. Furthermore, ginkgetin selectively inhibited the growth of prostate tumor cells stimulated with activated STAT3. Ginkgetin induced STAT3 dephosphorylation at Try705 and inhibited its localization to the nucleus, leading to the inhibition of expression of STAT3 target genes such as cell survival-related genes (cyclin D1 and survivin) and anti-apoptotic proteins (Bcl-2 and Bcl-xL) [2]. Ginkgetin suppressed the viability of PC-3 cells in a concentration-dependent manner and also significantly increased the sub-G1 DNA contents of cell cycle in PC-3 cells. Ginkgetin activated caspase-3 and attenuated the expression of survival genes such as Bcl-2, Bcl-xL, survivin and Cyclin D1 at protein and mRNA levels [3]. Ginkgetin (1 - 10 microM) and the biflavonoid mixture (10 - 50 microg/ml), mainly a 1 : 1 mixture of ginkgetin and isoginkgetin, from G. biloba leaves, inhibited production of prostaglandin E2 from lipopolysaccharide-induced RAW 264.7 cells [4].in vivo: Ginkgetin inhibited tumor growth in xenografted nude mice and down-regulated p-STAT3Tyr705 and survivin in tumor tissues [2]. At total doses of 1,000 microg/site on the dorsal skin (15 mm x 15 mm), ginkgetin inhibited prostaglandin E2 production by 65.6 % along with a marked suppression of COX-2 induction. In addition, ginkgetin and the biflavonoid mixture (100 - 1,000 microg/ear) dose-dependently inhibited skin inflammation of croton oil induced ear edema in mice by topical application [4]. |
This table lists Chinese names, IUPAC names and various aliases of this chemical substance.
| Name | ginkgetin |
|---|---|
| Synonym | More Synonyms |
This table contains bioactivity, target information and biological‑assay experimental data of this compound.
| Description | Ginkgetin is a natural biflavonoid isolated from leaves of Ginkgo biloba L; effects of anti-inflammation and anticancer have been reported.IC50 value:Target:in vitro: Ginkgetin inhibits COX-2 dependent phases of prostaglandin D(2) (PGD(2)) generation in bone marrow-derived mast cells (BMMC) in a concentration-dependent manner with IC(50) values of 0.75 microM. Ginkgetin consistently inhibited the production of leukotriene C(4) (LTC(4)) in a dose dependent manner, with an IC(50) value of 0.33 microM. Ginkgetin also inhibited degranulation reaction in a dose dependent manner, with an IC(50) value of 6.52 microM [1]. Ginkgetin inhibited both inducible and constitutively activated STAT3 and blocked the nuclear translocation of p-STAT3 in DU-145 prostate cancer cells. Furthermore, ginkgetin selectively inhibited the growth of prostate tumor cells stimulated with activated STAT3. Ginkgetin induced STAT3 dephosphorylation at Try705 and inhibited its localization to the nucleus, leading to the inhibition of expression of STAT3 target genes such as cell survival-related genes (cyclin D1 and survivin) and anti-apoptotic proteins (Bcl-2 and Bcl-xL) [2]. Ginkgetin suppressed the viability of PC-3 cells in a concentration-dependent manner and also significantly increased the sub-G1 DNA contents of cell cycle in PC-3 cells. Ginkgetin activated caspase-3 and attenuated the expression of survival genes such as Bcl-2, Bcl-xL, survivin and Cyclin D1 at protein and mRNA levels [3]. Ginkgetin (1 - 10 microM) and the biflavonoid mixture (10 - 50 microg/ml), mainly a 1 : 1 mixture of ginkgetin and isoginkgetin, from G. biloba leaves, inhibited production of prostaglandin E2 from lipopolysaccharide-induced RAW 264.7 cells [4].in vivo: Ginkgetin inhibited tumor growth in xenografted nude mice and down-regulated p-STAT3Tyr705 and survivin in tumor tissues [2]. At total doses of 1,000 microg/site on the dorsal skin (15 mm x 15 mm), ginkgetin inhibited prostaglandin E2 production by 65.6 % along with a marked suppression of COX-2 induction. In addition, ginkgetin and the biflavonoid mixture (100 - 1,000 microg/ear) dose-dependently inhibited skin inflammation of croton oil induced ear edema in mice by topical application [4]. |
|---|---|
| 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 | 1.5±0.1 g/cm3 |
|---|---|
| Boiling Point | 863.7±65.0 °C at 760 mmHg |
| Melting Point | 336ºC |
| Molecular Formula | C32H22O10 |
| Molecular Weight | 566.511 |
| Flash Point | 287.2±27.8 °C |
| Exact Mass | 566.121277 |
| PSA | 159.80000 |
| LogP | 4.45 |
| Vapour Pressure | 0.0±0.3 mmHg at 25°C |
| Index of Refraction | 1.714 |
| InChIKey | AIFCFBUSLAEIBR-UHFFFAOYSA-N |
| SMILES | COc1cc(O)c2c(=O)cc(-c3ccc(OC)c(-c4c(O)cc(O)c5c(=O)cc(-c6ccc(O)cc6)oc45)c3)oc2c1 |
| Storage condition | -20°C |
This table presents publicly reported synthetic routes, reaction conditions, reactants and product information of the compound.
|
~96%
ginkgetin CAS#:481-46-9 |
| Literature: Muller, Dominique; Fleury, Jean-Pierre Tetrahedron Letters, 1991 , vol. 32, # 20 p. 2229 - 2232 |
|
~%
ginkgetin CAS#:481-46-9 |
| Literature: Muller, Dominique; Fleury, Jean-Pierre Tetrahedron Letters, 1991 , vol. 32, # 20 p. 2229 - 2232 |
|
~%
ginkgetin CAS#:481-46-9 |
| Literature: Muller, Dominique; Fleury, Jean-Pierre Tetrahedron Letters, 1991 , vol. 32, # 20 p. 2229 - 2232 |
This table lists upstream starting materials and downstream derivative products related to this chemical.
| Precursor 1 | |
|---|---|
| DownStream 2 | |
CAS#:7507-89-3
CAS#:99-93-4This 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.
| 7,4'-di-O-methylamentoflavone |
| Amentoflavone 7,4'-dimethyl ether |
| 5,7-Dihydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxo-4H-chromen-2-yl)-2-methoxyphenyl]-2-(4-hydroxyphenyl)-4H-chromen-4-one |
| ginkgetin |
| 5,7-dihydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)-2-methoxyphenyl]-2-(4-hydroxyphenyl)chromen-4-one |
This section contains frequently‑asked‑questions about this compound, including basic parameters, properties, storage conditions and corresponding answers.
| Q: What is the melting point of ginkgetin? |
| A: Melting point of ginkgetin is 336ºC. |
| Q: What is the boiling point of ginkgetin? |
| A: Boiling point of ginkgetin is 863.7±65.0 °C at 760 mmHg. |
| Q: What English synonyms does ginkgetin have? |
| A: English synonyms of ginkgetin: 7,4'-di-O-methylamentoflavone, Amentoflavone 7,4'-dimethyl ether, 5,7-Dihydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxo-4H-chromen-2-yl)-2-methoxyphenyl]-2-(4-hydroxyphenyl)-4H-chromen-4-one, ginkgetin, 5,7-dihydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)-2-methoxyphenyl]-2-(4-hydroxyphenyl)chromen-4-one. |
| Q: What is the molecular formula of ginkgetin? |
| A: Molecular formula of ginkgetin is C32H22O10. |
| Q: What is the English name of ginkgetin? |
| A: The English name of ginkgetin is ginkgetin. |
| Q: What is the polar surface area (PSA) of ginkgetin? |
| A: Polar surface area (PSA) of ginkgetin is 159.80000. |
| Q: What are the storage conditions for ginkgetin? |
| A: Storage conditions for ginkgetin: -20°C. |
| Q: What is the InChIKey of ginkgetin? |
| A: InChIKey of ginkgetin is AIFCFBUSLAEIBR-UHFFFAOYSA-N. |
| Q: What is the CAS number of ginkgetin? |
| A: CAS number of ginkgetin is 481-46-9. |
| Q: What is the LogP of ginkgetin? |
| A: LogP of ginkgetin is 4.45. |
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. |