Lactupicrin
Basic information
- CAS
65725-11-3- Standard SMILES
C=C1C(=O)O[C@@H]2[C@H]3C(CO)=CC(=O)C3=C(C)C[C@H](OC(=O)Cc3ccc(O)cc3)[C@@H]12- InChIKey
UMVSOHBRAQTGQI-XGARDCMYSA-N- Molecular formula
- C23H22O7
- Average molar mass
- 410.4 g/mol
- Monoisotopic mass
- 410.13655304
Overview
Lactucopicrin is a sesquiterpene lactone obtained by formal condensation of the carboxy group of 4-hydroxyphenylacetic acid with the 8-hydroxy group of lactucin. Found in chicory. It has a role as a sedative, an antimalarial and a plant metabolite. It is a primary alcohol, a member of phenols, a cyclic terpene ketone, a sesquiterpene lactone, an azulenofuran and an enone. It is functionally related to a 4-hydroxyphenylacetic acid and a lactucin.
Names & identifiers
- Preferred name
- Lactupicrin
- IUPAC
- [(3aR,4S,9aS,9bR)-9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl] 2-(4-hydroxyphenyl)acetate
- English name
- Lactucopicrin
- Molecular formula
- C23H22O7
- Molecular weight
- 410.42
Names & synonyms
Lactupicrin65725-11-3Lactopicrin(3aR,4S,9aS,9bR)-9-(Hydroxymethyl)-6-methyl-3-methylene-2,7-dioxo-2,3,3a,4,5,7,9a,9b-octahydroazuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetateC09490MEGxp0_000597ACon1_000375Lactupicrin (Standard)2X2K7C7FWMCHEBI:6360orb1682243orb2900167
Show more names
[(3aR,4S,9aS,9bR)-9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl] 2-(4-hydroxyphenyl)acetateBenzeneacetic acid, 4-hydroxy-, (3aR,4S,9aS,9bR)-2,3,3a,4,5,7,9a,9b-octahydro-9-(hydroxymethyl)-6-methyl-3-methylene-2,7-dioxoazuleno[4,5-b]furan-4-yl ester
SCHEMBL14215977CHEBI:90275GTPL12499HY-N8290RDTXSID80984273HY-N8290TN4403AKOS040761962
Database identifiers
Properties
Computed structural properties
- XLogP
- 1.1
- Topological polar surface area
- 110 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 5
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 844
Physicochemical properties
- Melting point
- 146 °C · 146 °C
- Boiling point
- 686 · 686.0±55.0 °C(Predicted)
- Density
- 1.4 · 1.40±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- form
- Solid
- pka
- 9.79 · 9.79±0.15(Predicted)
- color
- White to off-white
- InChIKey
- UMVSOHBRAQTGQI-XGARDCMYSA-N
- SMILES
- C1(CC(O[C@@H]2[C@@]3([H])C(=C)C(=O)O[C@]3([H])[C@]3([H])C(C(=O)C=C3CO)=C(C)C2)=O)=CC=C(O)C=C1
- LogP
- 2.24 · 2.240 (est)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 317 · H317
- Precautionary statements
- 280 · P280-P302+P352
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H317
- Hazard Classifications
- Skin Sens. 1
- Precautionary statements
- P280-P302+P352
Chemistry & industry
Applications
UsesLactupicrin (Lactucopicrin) exhibits analgesic, sedative, antimalarial activities and atheroprotective effect. Lactupicrin inhibits acetylcholinesterase (AChE) with an IC50 of 150.3 μM. Lactupicrin is an orally active characteristic bitter sesquiterpene lactone[1][2][3][4][5].
Additional notes
DefinitionChEBI: Lactucopicrin is an azulenofuran, a cyclic terpene ketone, an enone, a member of phenols, a sesquiterpene lactone and a primary alcohol. It has a role as a plant metabolite, a sedative and an antimalarial. It is functionally related to a 4-hydroxyphenylacetic acid and a lactucin.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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