Lactucopicrin | CAS#6466-74-6 | sesquiterpene

MedKoo Cat#: 145448 | Name: Lactucopicrin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lactucopicrin is a bitter sesquiterpene lactone of leafy vegetables, such as chicory, curly escarole, and lettuce, possesses anti-malarial, anti-cancer and analgesic properties. Lactucopicrin inhibits NF-κB activation. Dietary lactucopicrin inhibits atherogenesis in mice likely by its anti-inflammatory property. Dietary supplementation with lactucopicrin is a promising strategy to inhibit atherosclerotic cardiovascular disease.

Chemical Structure

Lactucopicrin

CAS#6466-74-6

Theoretical Analysis

MedKoo Cat#: 145448

Name: Lactucopicrin

CAS#: 6466-74-6

Chemical Formula: C23H22O7

Exact Mass: 410.1400

Molecular Weight: 410.42

Elemental Analysis: C, 67.31; H, 5.40; O, 27.29

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Lactucopicrin; Intybin;

IUPAC/Chemical Name

((3aR,4S,9aS,9bR)-4-hydroxy-6-methyl-3-methylene-2,7-dioxo-2,3,3a,4,5,7,9a,9b-octahydroazuleno[4,5-b]furan-9-yl)methyl 2-(4-hydroxyphenyl)acetate

InChi Key

QCDLLIUTDGNCPO-AEMJNJESSA-N

InChi Code

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

SMILES Code

[H][C@@]12[C@@H](O)CC(C)=C3C(=O)C=C(COC(=O)CC4=CC=C(O)C=C4)[C@]3([H])[C@@]1([H])OC(=O)C2=C

Appearance

To be determined

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 410.42 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: He L, Weng H, Li Q, Shi G, Liu X, Du Y, Zheng J, Ling W, Wang D. Lactucopicrin Inhibits Cytoplasmic Dynein-Mediated NF-κB Activation in Inflammated Macrophages and Alleviates Atherogenesis in Apolipoprotein E-Deficient Mice. Mol Nutr Food Res. 2021 Feb;65(4):e2000989. doi: 10.1002/mnfr.202000989. Epub 2021 Jan 22. PMID: 33377310. 2: Weng H, He L, Liu X, Li Q, Du Y, Zheng J, Wang D. Natural lactucopicrin alleviates importin-α3-mediated NF-κB activation in inflammated endothelial cells and improves sepsis in mice. Biochem Pharmacol. 2021 Apr;186:114501. doi: 10.1016/j.bcp.2021.114501. Epub 2021 Mar 6. PMID: 33684389. 3: Li Q, Liu X, Zhang X, Du Y, Chen G, Xiang P, Ling W, Wang D. Terpene Lactucopicrin Limits Macrophage Foam Cell Formation by a Reduction of Lectin- Like Oxidized Low-Density Lipoprotein Receptor-1 in Lipid Rafts. Mol Nutr Food Res. 2022 Feb;66(4):e2100905. doi: 10.1002/mnfr.202100905. Epub 2021 Dec 29. PMID: 34932892. 4: Aibaidula Y, Aimaiti M, Tan H, Chen B, Yang J, Ma X. Lactucin & Lactucopicrin ameliorates FFA-induced steatosis in HepG2 cells via modulating lipid metabolism. J Pharmacol Sci. 2022 Oct;150(2):110-122. doi: 10.1016/j.jphs.2022.07.007. Epub 2022 Aug 6. PMID: 36055749. 5: Venkatesan R, Shim WS, Yeo EJ, Kim SY. Lactucopicrin potentiates neuritogenesis and neurotrophic effects by regulating Ca2+/CaMKII/ATF1 signaling pathway. J Ethnopharmacol. 2017 Feb 23;198:174-183. doi: 10.1016/j.jep.2016.12.035. Epub 2016 Dec 21. PMID: 28011163. 6: Venkatesan R, Subedi L, Yeo EJ, Kim SY. Lactucopicrin ameliorates oxidative stress mediated by scopolamine-induced neurotoxicity through activation of the NRF2 pathway. Neurochem Int. 2016 Oct;99:133-146. doi: 10.1016/j.neuint.2016.06.010. Epub 2016 Jun 22. PMID: 27346436. 7: Rotondo R, Oliva MA, Staffieri S, Castaldo S, Giangaspero F, Arcella A. Implication of Lactucopicrin in Autophagy, Cell Cycle Arrest and Oxidative Stress to Inhibit U87Mg Glioblastoma Cell Growth. Molecules. 2020 Dec 10;25(24):5843. doi: 10.3390/molecules25245843. PMID: 33322048; PMCID: PMC7764785. 8: Zhang X, Lan D, Ning S, Ruan L. Anticancer action of lactucopicrin in SKMEL-5 human skin cancer cells is mediated via apoptosis induction, G2/M cell cycle arrest and downregulation of m=TOR/PI3K/AKT signalling pathway. J BUON. 2018 Jan-Feb;23(1):224-228. PMID: 29552788. 9: Meng Q, Tang B, Qiu B. Growth inhibition of Saos-2 osteosarcoma cells by lactucopicrin is mediated via inhibition of cell migration and invasion, sub-G1 cell cycle disruption, apoptosis induction and Raf signalling pathway. J BUON. 2019 Sep-Oct;24(5):2136-2140. PMID: 31786886. 10: García CJ, Beltrán D, Tomás-Barberán FA. Human Gut Microbiota Metabolism of Dietary Sesquiterpene Lactones: Untargeted Metabolomics Study of Lactucopicrin and Lactucin Conversion In Vitro and In Vivo. Mol Nutr Food Res. 2020 Nov;64(21):e2000619. doi: 10.1002/mnfr.202000619. Epub 2020 Oct 7. PMID: 32970341. 11: Abudurexiti A, Abdurahman A, Zhang R, Zhong Y, Lei Y, Qi S, Hou W, Ma X. Screening of α-Glucosidase Inhibitors in Cichorium glandulosum Boiss. et Huet Extracts and Study of Interaction Mechanisms. ACS Omega. 2024 Apr 18;9(17):19401-19417. doi: 10.1021/acsomega.4c00699. PMID: 38708260; PMCID: PMC11064185. 12: Loth H, Schenck G, Walter F. Die Oxydation des Lactucopikrins und der p-Hydroxyphenylessigsaure durch Peroxydase [Oxidation of lactucopicrin and p-hydroxyphenylacetic acid by peroxydase]. Arch Pharm Ber Dtsch Pharm Ges. 1966 Apr;299(4):303-12. German. doi: 10.1002/ardp.19662990404. PMID: 5222266. 13: Bischoff TA, Kelley CJ, Karchesy Y, Laurantos M, Nguyen-Dinh P, Arefi AG. 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. PMID: 15507374. 14: Khalil AT, El-Fattah HA, Mansour ES. Guaianolides from Lactuca saligna. Planta Med. 1991 Apr;57(2):190-1. doi: 10.1055/s-2006-960064. PMID: 17226150. 15: SCHENCK G, LOTH H, REUBERT W. [Research on the preparation of lactucin and lactucopicrin from Lactuca virosa plants. 15. On the enzymatic and non-enzymatic oxidation of therapeutically active plant substances]. Arch Pharm Ber Dtsch Pharm Ges. 1961 Jan;294/66:17-24. German. doi: 10.1002/ardp.19612940105. PMID: 13747469. 16: Yang J, Zhang X, Mijiti Y, Sun Y, Jia M, Liu Z, Huang Y, Aisa HA. Improving performance of molecularly imprinted polymers prepared with template of low purity utilizing the strategy of macromolecular crowding. J Chromatogr A. 2020 Aug 2;1624:461155. doi: 10.1016/j.chroma.2020.461155. Epub 2020 May 12. PMID: 32540056. 17: Stojanović M, Savić S, Delcourt A, Hilbert JL, Hance P, Dragišić Maksimović J, Maksimović V. Phenolics and Sesquiterpene Lactones Profile of Red and Green Lettuce: Combined Effect of Cultivar, Microbiological Fertiliser, and Season. Plants (Basel). 2023 Jul 11;12(14):2616. doi: 10.3390/plants12142616. PMID: 37514230; PMCID: PMC10383302. 18: Wesołowska A, Nikiforuk A, Michalska K, Kisiel W, Chojnacka-Wójcik E. Analgesic and sedative activities of lactucin and some lactucin-like guaianolides in mice. J Ethnopharmacol. 2006 Sep 19;107(2):254-8. doi: 10.1016/j.jep.2006.03.003. Epub 2006 Mar 17. PMID: 16621374. 19: Lang R, Lang T, Dunkel A, Ziegler F, Behrens M. Overlapping activation pattern of bitter taste receptors affect sensory adaptation and food perception. Front Nutr. 2022 Dec 19;9:1082698. doi: 10.3389/fnut.2022.1082698. PMID: 36601079; PMCID: PMC9806268. 20: Jaśkiewicz A, Budryn G, Carmena-Bargueño M, Pérez-Sánchez H. Evaluation of Activity of Sesquiterpene Lactones and Chicory Extracts as Acetylcholinesterase Inhibitors Assayed in Calorimetric and Docking Simulation Studies. Nutrients. 2022 Sep 2;14(17):3633. doi: 10.3390/nu14173633. PMID: 36079888; PMCID: PMC9459812.