11beta,13-DihydrolactucinCAS# 83117-63-9 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 83117-63-9 | SDF | Download SDF |
| PubChem ID | 9970764 | Appearance | Powder |
| Formula | C15H18O5 | M.Wt | 278.3 |
| Type of Compound | Sesquiterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (3S,3aR,4S,9aS,9bR)-4-hydroxy-9-(hydroxymethyl)-3,6-dimethyl-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione | ||
| SMILES | CC1C2C(CC(=C3C(C2OC1=O)C(=CC3=O)CO)C)O | ||
| Standard InChIKey | ZHZZKRDEPZMPLJ-WLVQVHLUSA-N | ||
| Standard InChI | InChI=1S/C15H18O5/c1-6-3-9(17)12-7(2)15(19)20-14(12)13-8(5-16)4-10(18)11(6)13/h4,7,9,12-14,16-17H,3,5H2,1-2H3/t7-,9-,12+,13-,14-/m0/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
11beta,13-Dihydrolactucin Dilution Calculator
11beta,13-Dihydrolactucin Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.5932 mL | 17.9662 mL | 35.9324 mL | 71.8649 mL | 89.8311 mL |
| 5 mM | 0.7186 mL | 3.5932 mL | 7.1865 mL | 14.373 mL | 17.9662 mL |
| 10 mM | 0.3593 mL | 1.7966 mL | 3.5932 mL | 7.1865 mL | 8.9831 mL |
| 50 mM | 0.0719 mL | 0.3593 mL | 0.7186 mL | 1.4373 mL | 1.7966 mL |
| 100 mM | 0.0359 mL | 0.1797 mL | 0.3593 mL | 0.7186 mL | 0.8983 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Chemical constituents from Lactuca plumieri (L.) Gren. & Godr. (Asteraceae).[Pubmed:33969755]
Nat Prod Res. 2021 May 8:1-5.
This is the first report concerning the natural products of the hitherto unstudied Lactuca plumieri (L.) Gren. & Godr., a member of the tribe Cichorieae (Asteraceae). From aerial parts and roots of this plant, five sesquiterpene lactones and one coumarin were isolated. The compounds were identified as sonchuside A, 11beta,13-Dihydrolactucin-8-O-acetate, 11beta,13-Dihydrolactucin, cichorioside B, 11beta,13-Dihydrolactucin-8-O-acetate-15-O-beta-glucopyranoside and coumarin - cichoriin. Their structures were established by (1)H NMR. Moreover, HPLC/PAD analysis of a hydroalcoholic extract from the aerial parts of the plant revealed the presence of caffeic acid derivatives, coumarins and flavonoids commonly found in lettuces.
Low Oral Bioavailability and Partial Gut Microbiotic and Phase II Metabolism of Brussels/Witloof Chicory Sesquiterpene Lactones in Healthy Humans.[Pubmed:33260567]
Nutrients. 2020 Nov 28;12(12). pii: nu12123675.
Free and glycosylated sesquiterpene lactones (SLs), which are abundant in leafy vegetables including Brussels/witloof chicory, possess health-promoting effects in vivo. However, the pharmacokinetics of dietary source of SLs remain largely unknown. In this open-label and single-dose trial, sixteen healthy volunteers consumed 150 g of Brussels/witloof chicory juice containing 48.77 mumol SLs in 5 min. Blood, urine, and fecal samples were collected before and after chicory consumption in 24 h. No SLs were detected in the serum, urine, and fecal samples before chicory consumption in all of the participants. Chicory consumption increased lactucin, 11beta,13-Dihydrolactucin, and their glucuronide/sulfate conjugates, rather than lactucopicrin and 11beta,13-dihydrolactucopicrin, as well as glycosylated SLs in biological samples. The peak concentration of total SLs in serum reached 284.46 nmol/L at 1 h, while, in urine, this peak was 220.3 nmol between 2 and 6 h. The recovery of total SLs in blood, urine, and feces was 7.03%, 1.13%, and 43.76% of the ingested dose, respectively. Human fecal suspensions with intestinal microbiota degraded glycosylated SLs in chicory, and converted lactucopicrin and 11beta,13-dihydrolactucopicrin to lactucin and 11beta,13-Dihydrolactucin, respectively. Collectively, Brussels/witloof chicory SLs are poorly bioavailable and they undergo partial gut microbial and phase II metabolism in humans.
Assessing the Intestinal Permeability and Anti-Inflammatory Potential of Sesquiterpene Lactones from Chicory.[Pubmed:33228214]
Nutrients. 2020 Nov 19;12(11). pii: nu12113547.
Cichorium intybus L. has recently gained major attention due to large quantities of health-promoting compounds in its roots, such as inulin and sesquiterpene lactones (SLs). Chicory is the main dietary source of SLs, which have underexplored bioactive potential. In this study, we assessed the capacity of SLs to permeate the intestinal barrier to become physiologically available, using in silico predictions and in vitro studies with the well-established cell model of the human intestinal mucosa (differentiated Caco-2 cells). The potential of SLs to modulate inflammatory responses through modulation of the nuclear factor of activated T-cells (NFAT) pathway was also evaluated, using a yeast reporter system. Lactucopicrin was revealed as the most permeable chicory SL in the intestinal barrier model, but it had low anti-inflammatory potential. The SL with the highest anti-inflammatory potential was 11beta,13-Dihydrolactucin, which inhibited up to 54% of Calcineurin-responsive zinc finger (Crz1) activation, concomitantly with the impairment of the nuclear accumulation of Crz1, the yeast orthologue of human NFAT.
Sesquiterpenoids with diverse carbon skeletons from the roots of Cichorium glandulosum and their anti-inflammatory activities.[Pubmed:31085308]
Fitoterapia. 2019 Jul;136:104170.
A total of thirteen sesquiterpenoids with diverse skeletons including four new sesquiterpenoids, glandulosines A-D (1-4), a new natural product, glandulosine E (5), and eight known sesquiterpene lactones (6-13) were isolated from the roots of Cichorium glandulosum Boiss. et Huet (Asteraceae). Their structures were determined by extensive spectroscopic experiments including NMR, electronic circular dichroism (ECD), calculated ECD, Rh2(OCOCF3)4-induced ECD, and single-crystal X-ray diffraction analysis, as well as chemical methods. This is the first report of the crystal structure of 11beta,13-Dihydrolactucin (11). Thirteen isolated sesquiterpenoids (1-13) were evaluated for their anti-inflammatory activities in vitro, and three guaiane sesquiterpene lactones, glandulosine E (5), scorzoside (9), and lactucin (10) showed moderate inhibitory activity against LPS-induced nitric oxide (NO) production in RAW 264.7 macrophages.
