7-Quinolinamine, 1,2,3,4-tetrahydro-4,4-dimethyl-
Basic information
- CAS
1891-29-8- Standard SMILES
C=C1C(=O)OC2C3C(CO)=CC(=O)C3=C(C)CC(O)C12- InChIKey
VJQAFLAZRVKAKM-UHFFFAOYSA-N- Molecular formula
- C15H16O5
- Average molar mass
- 276.28 g/mol
- Monoisotopic mass
- 276.09977361
Overview
4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione has been reported in Ixeris, Cichorium endivia, and other organisms with data available.
Names & identifiers
- Preferred name
- 7-Quinolinamine, 1,2,3,4-tetrahydro-4,4-dimethyl-
- IUPAC
- 4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione
- English name
- LACTUCIN
- Molecular formula
- C15H16O5
- Molecular weight
- 276.28
Names & synonyms
7-Quinolinamine, 1,2,3,4-tetrahydro-4,4-dimethyl-109402-60-04-Hydroxy-9-(hydroxymethyl)-6-methyl-3-methylene-3,3a,4,5-tetrahydroazuleno[4,5-b]furan-2,7(9aH,9bH)-dione4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dioneSCHEMBL235693orb3178793TN12402LACTUCINLactucine(3aR)-3,3aβ,4,5,9aβ,9bα-Hexahydro-4α-hydroxy-9-(hydroxymethyl)-6-methyl-3-methyleneazuleno[4,5-b]furan-2,7-dione(3aR,4S,9aS,9bR)-3,3a,4,5,9a,9b-Hexahydro-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methyleneazuleno[4,5-b]furan-2,7-dione(3aR,4S,9aS,9bR)-4-Hydroxy-9-(hydroxymethyl)-6-methyl-3-methylene-3,3a,4,5-tetrahydroazuleno[4,5-b]furan-2,7(9aH,9bH)-dione
Show more names
Azuleno[4,5-b]furan-2,7-dione, 3,3a,4,5,9a,9b-hexahydro-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylene-, (3aR,4S,9aS,9bR)-
Database identifiers
Properties
Computed structural properties
- XLogP
- -0.7
- Topological polar surface area
- 83.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 1
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 583
Experimental & physicochemical properties
Melting Point224 - 228 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 228 · 228-233°
- alpha
- 49 ° · D +49° (c = 0.90 in methanol), +77.9° (c = 3.44 in pyridine)
- Boiling point
- 575.6 · 575.6±50.0 °C(Predicted)
- Density
- 1.39 · 1.39±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- pka
- 13.53 · 13.53±0.60(Predicted)
- form
- solid
- InChI
- 1S/C15H16O5/c1-6-3-9(17)12-7(2)15(19)20-14(12)13-8(5-16)4-10(18)11(6)13/h4,9,12-14,16-17H,2-3,5H2,1H3/t9-,12+,13-,14-/m0/s1
- InChIKey
- VJQAFLAZRVKAKM-VZLIPTOUSA-N
- SMILES
- O1[C@H]2[C@@H]([C@H](CC(=C3[C@@H]2C(=CC3=O)CO)C)O)C(=C)C1=O
- LogP
- 0.33 · 0.330 (est)
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
Pharmacology
Cellular LocationsCytoplasm
Applications
DescriptionLactucin, as lactucopicrin, is a sesquiterpene lactone contained in lettuce (Lactuca sativa).
UsesLactucin is an anti-inflammatory agent. Lactucin induces cancer cell apoptosis. Lactucin also shows analgesic, anticancer and antimalarial activities[1][2][3][4].
Additional notes
DefinitionChEBI: An azulenofuran that is 3-methylidene-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione carrying additional hydroxy, methyl and hydroxymethyl substituents at positions 4, 6 and 9 respectively (the 3aR,4S,9 S,9bR-diastereomer). Found in chicory.
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