Introduction：Basic information about CAS 21187-73-5|Gardenin A, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Gardenin A |
|---|
| CAS Number | 21187-73-5 | Molecular Weight | 418.39400 |
|---|
| Density | 1.3g/cm3 | Boiling Point | 624.2ºC at 760 mmHg |
|---|
| Molecular Formula | C21H22O9 | Melting Point | 162-163ºC |
|---|
| MSDS | / | Flash Point | 218.5ºC |
|---|
Names
| Name | 5-hydroxy-6,7,8-trimethoxy-2-(3,4,5-trimethoxyphenyl)chromen-4-one |
|---|
| Synonym | More Synonyms |
|---|
Gardenin A BiologicalActivity
| Description | Gardenin A is an orally active and synthetic PMF analogue with the neurotrophic effect for neurite outgrowth and neuronal differentiation. Gardenin A promotes neuritogenesis via activating MAPK/ERK, PKC, and PKA, but not TrkA, CREB signaling pathways. Gardenin A also has sedative, anxiolytic, antidepressant, and anticonvulsant effects[1][2]. |
|---|
| Related Catalog | Signaling Pathways >>Cytoskeleton >>PAKResearch Areas >>Inflammation/ImmunologySignaling Pathways >>MAPK/ERK Pathway >>ERKResearch Areas >>Neurological DiseaseSignaling Pathways >>Cell Cycle/DNA Damage >>PAKSignaling Pathways >>Stem Cell/Wnt >>ERK |
|---|
| In Vitro | Gardenin A (10-20 μM; 48 h) 可诱导 PC12 细胞神经突生长，(10 μM; 24 小时和 48 小时) 还增加神经元分化和突触形成标记蛋白、生长相关蛋白-43 (GAP-43) 和突触素的表达[1]。 Gardenin A (10 μM; 30-120分钟) 显著诱导环 AMP 反应元件结合蛋白(CREB) 的磷酸化和 CRE 介导的转录，这是通过抑制剂 2-萘酚AS-E 磷酸盐 (KG-501) 或使用 CREB siRNA 来抑制的[1]。 Gardenin A (10 μM; 15-120分钟) 增加 ERK 磷酸化水平，提高 PKA 和 PKC 活性[1]。 Cell Viability Assay[1] Cell Line: PC12 cells Concentration: 2, 5, 10, 20 μM Incubation Time: 48 hours Result: showed cell growth supporting effect at higher concentrations (10-20 µM) and did not exert detectable 237 cytotoxicity on PC12 cells after 48 h incubation in low serum medium. Western Blot Analysis[1] Cell Line: PC12 cells Concentration: 10 μM Incubation Time: 0, 15, 30, 60, and 120 min Result: Significantly increased the phosphorylation of ERK1/2 (Thr202/Tyr204) at 15 min, subsequently reduced after 30 min. Increased PKC and PKA activity peaked at 15 min.Increased CREB phosphorylation. |
|---|
| In Vivo | Gardenin A (0.1-25 mg/kg; 口服; 单剂量) 具有神经药理作用，包括镇静、抗焦虑、抗抑郁和抗惊厥作用的小鼠[2]。 栀子苷A (1-10 mg/kg; 口服; 单次剂量) 不影响小鼠的运动协调和延迟惊厥的发生[2]。 Animal Model: Male Balb/c mice (24-32 g)[2] Dosage: 1 mg/kg, 10 mg/kg, 25 mg/kg Administration: Oral gavage; single dose Result: Showed sedative effects at a dose of 25 mg/kg, which increased the duration of sleep but did not alter sleep onset. |
|---|
| References | [1]. Chiu SP, et al. Neurotrophic action of 5-hydroxylated polymethoxyflavones: 5-demethylnobiletin and gardenin A stimulate neuritogenesis in PC12 cells. J Agric Food Chem. 2013 Oct 2;61(39):9453-63. [2]. Alonso-Castro AJ, et al. Evaluation of the neuropharmacological effects of Gardenin A in mice. Drug Dev Res. 2020 Aug;81(5):600-608. |
|---|
Chemical & Physical Properties
| Density | 1.3g/cm3 |
|---|
| Boiling Point | 624.2ºC at 760 mmHg |
|---|
| Melting Point | 162-163ºC |
|---|
| Molecular Formula | C21H22O9 |
|---|
| Molecular Weight | 418.39400 |
|---|
| Flash Point | 218.5ºC |
|---|
| Exact Mass | 418.12600 |
|---|
| PSA | 105.82000 |
|---|
| LogP | 3.21720 |
|---|
| Vapour Pressure | 3.57E-16mmHg at 25°C |
|---|
| Index of Refraction | 1.573 |
|---|
| InChIKey | MQBFFYQCZCKSBX-UHFFFAOYSA-N |
|---|
| SMILES | COc1cc(-c2cc(=O)c3c(O)c(OC)c(OC)c(OC)c3o2)cc(OC)c1OC |
|---|
| Storage condition | -20°C |
|---|
Safety Information
| Hazard Codes | T+ |
|---|
| HS Code | 2914509090 |
|---|
Customs
| HS Code | 2914509090 |
|---|
| Summary | HS:2914509090 other ketones with other oxygen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0% |
|---|
Synonyms
| Gardenin A |
| 5OH3'4'5'6,7,8-hexMeO-Flavone |
| 3',4',5',6,7,8-Hexamethoxy-5-hydroxyflavone |
| Gardenin |
| 5-hydroxy-6,7,8,3',4',5'-hexamethoxyflavone |
| Flavone,5-hydroxy-3',4',5',6,7,8-hexamethoxy |
