4H-1-Benzopyran-4-one,5,6,7,8-tetramethoxy-2-(3,4,5-trimethoxyphenyl)-

Modify Date: 2024-01-03 13:19:42

4H-1-Benzopyran-4-one,5,6,7,8-tetramethoxy-2-(3,4,5-trimethoxyphenyl)- Structure
4H-1-Benzopyran-4-one,5,6,7,8-tetramethoxy-2-(3,4,5-trimethoxyphenyl)- structure
Common Name 4H-1-Benzopyran-4-one,5,6,7,8-tetramethoxy-2-(3,4,5-trimethoxyphenyl)-
CAS Number 6965-36-2 Molecular Weight 432.42100
Density 1.245g/cm3 Boiling Point 611.7ºC at 760 mmHg
Molecular Formula C22H24O9 Melting Point N/A
MSDS N/A Flash Point 265ºC

 Use of 4H-1-Benzopyran-4-one,5,6,7,8-tetramethoxy-2-(3,4,5-trimethoxyphenyl)-


5'-Methoxynobiletin is a potent and orally active antinociceptive and anti-inflammatory agent. 5'-Methoxynobiletin is a polymethoxyflavone, that can be isolated from A. conyzoides[1][2].

 Names

Name 2-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one
Synonym More Synonyms

  Biological Activity

Description 5'-Methoxynobiletin is a potent and orally active antinociceptive and anti-inflammatory agent. 5'-Methoxynobiletin is a polymethoxyflavone, that can be isolated from A. conyzoides[1][2].
Related Catalog
In Vivo 5'-Methoxynobiletin (5mg /kg, 腹腔注射) 可显著降低白细胞计数、中性粒细胞流入和渗出液中的蛋白质浓度,并降低几种促炎介质的水平[2]。< br/>5'-Methoxynobiletin (100 mg/kg,口服,一次) 显示出抗伤害和抗炎活性[2]。 5'-Methoxynobiletin (10 mg/kg,静脉注射;50 mg/kg,口服;一次) 在大鼠体内的口服生物利用度较低,约为 8-11%[2]。 Animal Model: Swiss mice (female)[2] Dosage: 100 mg/kg Administration: Orally Result: Significantly reduced both phases of formalin-induced nocifensive behavior after 15, 30 and 60 min of oral administration, when compared to control groups. In the neurogenic phase, inhibitions of 43±3%, 68±6% and 53±5% of the nociceptive response were observed, while for the infammatory phase inhibitions were 70±8%, 91±3% and 85±3% after 15, 30 and 60 min of the oral administration of 5'-Methoxynobiletin, respectively. Animal Model: Wistar rats (male)[2] Dosage: 10 mg/kg (IV), 50 mg/kg (oral) Administration: IV, oral, once (Pharmacokinetic Analysis) Result: Pharmacokinetic Parameters of 5'-Methoxynobiletin in male Wistar rats[1]. IV (10 mg/kg) IG (50 mg/kg) λ (h-1) 0.55±0.03 0.29±0.2 Tmax (h) 2.71±0.49 Cmax (mg/L) 0.62±0.21 AUC0-∞ (mg·h/L) 8.19±4.1 3.65±0.8 t1/2 elimination (h) 1.26±0.1 2.31±0.9 CL (L/h.kg) 1.22±0.26 13.68±0.29 Vd, ss (L/kg) 2.24±0.32 47.46±10.10 F (%) 8.67
References

[1]. Faqueti LG, et al. Antinociceptive and anti-inflammatory activities of standardized extract of polymethoxyflavones from Ageratum conyzoides. J Ethnopharmacol. 2016 Dec 24;194:369-377.  

[2]. Faqueti LG, et al. Preclinical Pharmacokinetic and Pharmacodynamic Investigation of 5'-Methoxynobiletin from Ageratum conyzoides: In vivo and In silico Approaches. Pharm Res. 2022 Sep;39(9):2135-2145.  

 Chemical & Physical Properties

Density 1.245g/cm3
Boiling Point 611.7ºC at 760 mmHg
Molecular Formula C22H24O9
Molecular Weight 432.42100
Flash Point 265ºC
Exact Mass 432.14200
PSA 94.82000
LogP 3.52020
Index of Refraction 1.551

 Synthetic Route

~84%

4H-1-Benzopyran-4-one,5,6,7,8-tetramethoxy-2-(3,4,5-trimethoxyphenyl)- Structure

4H-1-Benzopyran...

CAS#:6965-36-2

Literature: Tsukayama, Masao; Kusunoki, Eiji; Hossain, Mohammad M.; Kawamura, Yasuhiko; Hayashi, Shinji Heterocycles, 2007 , vol. 71, # 7 p. 1589 - 1600

~%

4H-1-Benzopyran-4-one,5,6,7,8-tetramethoxy-2-(3,4,5-trimethoxyphenyl)- Structure

4H-1-Benzopyran...

CAS#:6965-36-2

Literature: Vyas, Ashok V.; Mulchandani, Newand B. Phytochemistry (Elsevier), 1986 , vol. 25, # 11 p. 2625 - 2628

~%

4H-1-Benzopyran-4-one,5,6,7,8-tetramethoxy-2-(3,4,5-trimethoxyphenyl)- Structure

4H-1-Benzopyran...

CAS#:6965-36-2

Literature: Balakrishna; Seshadri Proceedings - Indian Academy of Sciences, Section A, 1948 , # 27 p. 91,102 Show Details Bose; Nath Journal of the Indian Chemical Society, 1938 , vol. 15, p. 139,147

~%

4H-1-Benzopyran-4-one,5,6,7,8-tetramethoxy-2-(3,4,5-trimethoxyphenyl)- Structure

4H-1-Benzopyran...

CAS#:6965-36-2

Literature: Banerji, J.; Das, B.; Chakrabarty, R.; Jha, H. C. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1988 , vol. 27, # 1-12 p. 597 - 599

 Synonyms

5,6,7,8-tetramethoxy-2-(3,4,5-trimethoxyphenyl)chromen-4-one
5,6,7,8-Tetramethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one
5'-methoxynobiletin
5,6,7,8-Tetramethoxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-on
5,6,7,8,3',4',5'-heptamethoxyflavone
5,6,7,8-tetramethoxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one
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