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26577-85-5

26577-85-5 Structure

26577-85-5 Structure
IdentificationBack Directory
[Name]

PETASIN
[CAS]

26577-85-5
[Synonyms]

Petaforce
O-Angeloylsencathenone
(Z)-2-Methyl-2-butenoic acid [(3S)-3α-isopropenyl-4aβ,5β-dimethyl-2,3,4,4a,5,6,7,8-octahydro-2-oxonaphthalene]-6α-yl ester
(Z)-2-Methyl-2-butenoic acid (1R)-1,2,3,4,6,7,8,8a-octahydro-1β,8aβ-dimethyl-7α-(1-methylethenyl)-6-oxonaphthalen-2α-yl ester
(2Z)-2-Methyl-2-butenoic acid (1R,2R,7S,8aR)-1,2,3,4,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-6-oxo-2-naphthalenyl ester
2-Butenoic acid, 2-methyl-, (1R,2R,7S,8aR)-1,2,3,4,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-6-oxo-2-naphthalenyl ester, (2Z)-
[Molecular Formula]

C20H28O3
[MOL File]

26577-85-5.mol
[Molecular Weight]

316.43
Chemical PropertiesBack Directory
[Melting point ]

66-70℃
[Boiling point ]

421.1±45.0 °C(Predicted)
[density ]

1.04±0.1 g/cm3(Predicted)
Hazard InformationBack Directory
[Uses]

Petasin inhibits adipogenesis in cell 3T3-F442A with an IC50 of 0.95 μM. Petasin inhibits the expression of lipid synthesis factors ACC1, FAS and SCD1 by inhibiting transcription factors PPARγ and C/EBPα, as well as targeting TRPA1 and TRPV1 channels . Petasin inhibits mitochondrial complex I, thereby inhibiting tumor growth and metastasis. Petasin activates AMPK signaling pathway, participating in regulation of glucose and lipid metabolism. Petasin is orally active[1].
[Definition]

ChEBI: An enoate ester obtained by formal condensation of the carboxy group of angelic acid with the hydroxy group of (1R,2R,7S,8aR)-1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahy ronaphthalen-2-ol.
[References]

[1] Uesugi S, et al., Petasin is the main component responsible for the anti-adipogenic effect of Petasites japonicus. Fitoterapia. 2022 Mar;157:105130. DOI:10.1016/j.fitote.2022.105130
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