Petasin

Names
IUPAC name

8-Oxo-7α-eremophila-9,11-dien-3α-yl (2Z)-2-methylbut-2-enoate

Systematic IUPAC name

(1R,2R,7S,8aR)-1,8a-Dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl (2Z)-2-methylbut-2-enoate

Other names

Petasol butenoate; O-Angeloylsencathenone

Identifiers

CAS Number

* 26577-85-5 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:8030 Y

ChemSpider |

* 4444859

PubChem CID

* 5281526

UNII |

* 9Z0Q32J0QC Y

InChI

* InChI=1S/C20H28O3/c1-7-13(4)19(22)23-18-9-8-15-10-17(21)16(12(2)3)11-20(15,6)14(18)5/h7,10,14,16,18H,2,8-9,11H2,1,3-6H3/b13-7-/t14-,16-,18+,20+/m0/s1

Key: ISTBXSFGFOYLTM-NZEDGPFZSA-N

* InChI=1/C20H28O3/c1-7-13(4)19(22)23-18-9-8-15-10-17(21)16(12(2)3)11-20(15,6)14(18)5/h7,10,14,16,18H,2,8-9,11H2,1,3-6H3/b13-7-/t14-,16-,18+,20+/m0/s1

Key: ISTBXSFGFOYLTM-NZEDGPFZBZ

SMILES

* O=C2/C=C1/CC[C@@H](OC(=O)\C(=C/C)C)[C@@H]([C@]1(C[C@H]2\C(=C)C)C)C

Properties

Chemical formula

| C20H28O3
Molar mass | 316.441 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Tracking categories (test):

* SizeSet

Petasin is a natural chemical compound found in plants of the genus Petasites. Chemically, it is classified as a sesquiterpene and is the ester of petasol and angelic acid.

Petasin is believed to be responsible, at least in part, for the anti-inflammatory effects of Common Butterbur (Petasites hybridus) extracts.[1]

Recent study has proven that Petasin can inhibit the tumor growth and metastasis in cancer patients.[2]

## References

1. ↑ Thomet, O; Wiesmann, UN; Schapowal, A; Bizer, C; Simon, HU (2001). "Role of petasin in the potential anti-inflammatory activity of a plant extract of petasites hybridus". Biochemical Pharmacology 61 (8): 1041–7. doi:10.1016/S0006-2952(01)00552-4. PMID 11286996.
2. ↑ Heishima, Kazuki; Sugito, Nobuhiko; Soga, Tomoyoshi; Nishikawa, Masashi; Ito, Yuko (2021). "Petasin potently inhibits mitochondrial complex I–based metabolism that supports tumor growth and metastasis". The Journal of Clinical Investigation 131 (17): e139933. doi:10.1172/JCI139933.

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*[CID]: Compound ID