Lactucopicrin

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Lactucopicrin
Stereo wireframe of a chiral lactucopicrin tautomer
Names
Preferred IUPAC name
(4-Hydroxy-6-methyl-3-methylidene-2,7-dioxo-

4,5,9a,9b-tetrahydro-3aH-azuleno[8,7-b]furan-

9-yl)methyl 2-(4-hydroxyphenyl)acetate
Systematic IUPAC name
{4-Hydroxy-6-methyl-3-methylidene-2,7-dioxo-

2H,3H,3aH,4H,5H,7H,8H,9bH-azuleno[4,5-b]

furan-9-yl}methyl 2-(4-hydroxyphenyl)acetate
Other names
{4-Hydroxy-6-methyl-3-methylidene-2,7-dioxo-

3aH,4H,5H,8H,9bH-azuleno[4,5-b]furan-9-yl}
methyl 2-(4-hydroxyphenyl)acetate

Intybin
Identifiers
6466-74-6 (3aR,4S,9bS)
ChemSpider 152483 (3aR,4S,9bS) N
Jmol 3D model Interactive image
MeSH Intybin
PubChem 174863 (3aR,4S,9bS)
  • InChI=1S/C23H22O7/c1-11-7-16(25)20-12(2)23(28)30-22(20)21-14(9-17(26)19(11)21)10-29-18(27)8-13-3-5-15(24)6-4-13/h3-6,9,16,20-22,24-25H,2,7-8,10H2,1H3/t16-,20+,21-,22-/m0/s1
    Key: QCDLLIUTDGNCPO-AEMJNJESSA-N
  • InChI=1/C23H22O7/c1-11-7-16(25)20-12(2)23(28)30-22(20)21-14(9-17(26)19(11)21)10-29-18(27)8-13-3-5-15(24)6-4-13/h3-6,9,16,20-22,24-25H,2,7-8,10H2,1H3/t16-,20+,21-,22-/m0/s1
    Key: QCDLLIUTDGNCPO-AEMJNJESBM
  • CC1=C2[C@@H]([C@@H]3[C@@H]([C@H](C1)O)C(=C)C(=O)O3)C(=CC2=O)COC(=O)Cc4ccc(cc4)O
Properties
C23H22O7
Molar mass 410.42 g·mol−1
Pharmacology
Oral, Smoked
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Lactucopicrin (Intybin) is a bitter substance that has a sedative and analgesic effect,[1] acting on the central nervous system. It is a sesquiterpene lactone, and is a component of lactucarium, derived from the plant Lactuca virosa (wild lettuce), as well as being found in some related plants such as Cichorium intybus.[2] It is also found in dandelion coffee.

As well as their traditional use as sedatives and analgesics, these plants have also been used as antimalarials, and both lactucin and lactucopicrin have demonstrated antimalarial effects in vitro.[3] Lactucopicrin has also been shown to act as an acetylcholinesterase inhibitor.[4]

See also

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.

External links

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