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| | LACTUCIN Basic information |
| Product Name: | LACTUCIN | | Synonyms: | LACTUCIN;(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;Lactucine;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)-;(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 | | CAS: | 1891-29-8 | | MF: | C15H16O5 | | MW: | 276.28 | | EINECS: | | | Product Categories: | | | Mol File: | 1891-29-8.mol |  |
| | LACTUCIN Chemical Properties |
| Melting point | 228-233° | | alpha | D +49° (c = 0.90 in methanol), +77.9° (c = 3.44 in pyridine) | | Boiling point | 575.6±50.0 °C(Predicted) | | density | 1.39±0.1 g/cm3(Predicted) | | storage temp. | 2-8°C | | pka | 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 | 0.330 (est) | | CAS DataBase Reference | 1891-29-8 |
| WGK Germany | WGK 3 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Skin Sens. 1 |
| | LACTUCIN Usage And Synthesis |
| Description | Lactucin, as lactucopicrin, is a sesquiterpene lactone
contained in lettuce (Lactuca sativa). | | Uses | Lactucin is an anti-inflammatory agent. Lactucin induces cancer cell apoptosis. Lactucin also shows analgesic, anticancer and antimalarial activities[1][2][3][4]. | | Definition | ChEBI: 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. | | Contact allergens | Lactucin, as lactucopicrin, is a sesquiterpene lactone contained in lettuce (Lactuca sativa L.) | | in vivo | Lactucin (15 and 30 mg/kg; i.p.; once) decreases the spontaneous locomotor activity and shows analgesic properties in mice[2]. | Animal Model: | Male Albino-Swiss mice (18-24 g)[2] | | Dosage: | 15 and 30 mg/kg | | Administration: | Intraperitoneal injection, once | | Result: | Decreased the spontaneous locomotor activity and showed analgesic properties in the hot plate test. |
| | References | [1] Dang T, et al. Sesquiterpenoids with diverse carbon skeletons from the roots of Cichorium glandulosum and their anti-inflammatory activities. Fitoterapia. 2019 Jul;136:104170. DOI:10.1016/j.fitote.2019.104170
[2] Gromek D, et al. Biologically active preparations from Lactuca virosa L. Phytotherapy Research, 1992, 6(5): 285-287.
[3] Zhang F H, et al. Lactucin induces potent anti-cancer effects in HL-60 human leukemia cancer cells by inducing apoptosis and sub-G1 cell cycle arrest. Bangladesh Journal of Pharmacology, 2016, 11(2): 478-484.
[4] Bischoff TA, et al. Antimalarial activity of lactucin and lactucopicrin: sesquiterpene lactones isolated from Cichorium intybus L. J Ethnopharmacol. 2004 Dec;95(2-3):455-7. DOI:10.1016/j.jep.2004.06.031 |
| | LACTUCIN Preparation Products And Raw materials |
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