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Helenin information


Helenin

Alantolactone

Isoalantolactone
Names
IUPAC names
Alantolactone: (3aR,5S,8aR,9aR)-5,8a-Dimethyl-3-methylene-3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(3H)-one
Isoalantolactone: (3aR,4aS,8aR,9aR)-8a-Methyl-3,5-bis(methylene)decahydronaphtho[2,3-b]furan-2(3H)-one
Other names
Elecampane camphor, Inula camphor, Alant camphor
Identifiers
CAS Number
  • Alantolactone: 546-43-0 checkY
  • isolantolactone: 470-17-7 checkY
3D model (JSmol)
  • Alantolactone: Interactive image
  • isolantolactone: Interactive image
ChEBI
  • Alantolactone: CHEBI:2540
  • isolantolactone: CHEBI:5981
ChEMBL
  • Alantolactone: ChEMBL136356
  • isolantolactone: ChEMBL137803
ChemSpider
  • Alantolactone: 65564
  • isolantolactone: 66028
EC Number
  • Alantolactone: 208-899-3
KEGG
  • Alantolactone: C09289
  • isolantolactone: C09484
PubChem CID
  • Alantolactone: 72724
  • isolantolactone: 73285
UNII
  • Alantolactone: M7GSN5Q1M6 checkY
  • isolantolactone: BYH07P620U checkY
InChI
  • InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h7,9,11,13H,2,4-6,8H2,1,3H3/t9-,11+,13+,15+/m0/s1
    Key: PXOYOCNNSUAQNS-AGNJHWRGSA-N
  • isolantolactone: InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h11-13H,1-2,4-8H2,3H3/t11-,12+,13-,15-/m1/s1
    Key: CVUANYCQTOGILD-QVHKTLOISA-N
SMILES
  • Alantolactone: C[C@H]1CCC[C@]2(C1=C[C@H]3[C@@H](C2)OC(=O)C3=C)C
  • isolantolactone: C[C@]12CCCC(=C)[C@@H]1C[C@H]3[C@@H](C2)OC(=O)C3=C
Properties
Chemical formula
C15H20O2
Molar mass 232.323 g·mol−1
Appearance Crystalline powder
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Helenin is a phytochemical mixture found in many plant species, including the Inula helenium (elecampane) of the family Asteraceae. It is a mixture of two isomeric sesquiterpene lactones, alantolactone and isoalantolactone.

In 1895 the German scientists Julius Bredt and Wilhelm Posh extracted helenin from Inula helenium and determined its physical and chemical properties.[1]

  1. ^ Chemical Society (Great Britain) (1895). The collected works of Sir Humphry Davy ...: Discourses delivered before the Royal society. Elements of agricultural chemistry, pt. I. Smith, elder and Company. p. 555. Retrieved 31 July 2015.

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