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Nortracheloside

Cat No.:V62233 Purity: ≥98%
Nortracheloside is a lignan extracted from Trachelospermum jasminoides (Lindl.) Lem.
Nortracheloside
Nortracheloside Chemical Structure CAS No.: 33464-78-7
Product category: Phenylpropanoids
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
10mg
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Product Description
Nortracheloside is a lignan extracted from Trachelospermum jasminoides (Lindl.) Lem.
Nortracheloside (CAS# 33464-78-7) is a lignan isolated from Trachelospermum jasminoides (Lindl.) Lem., a plant widely used for antipyretic and analgesic purposes. It has the molecular formula C27H34O12 and a molecular weight of 550.55. Nortracheloside demonstrates anti-inflammatory activity by inhibiting LPS-induced nitric oxide production in mouse RAW264.7 cells. The compound has been recognized as an active component capable of reducing allergen permeation and enhancing intestinal barrier function, showing potential to attenuate food allergy and inflammatory bowel disease through immunoregulatory bioactivity.
Biological Activity I Assay Protocols (From Reference)
Targets
Nortracheloside targets inflammatory pathways by inhibiting LPS-induced nitric oxide production in macrophages. The compound exhibits anti-inflammatory, antitumor, and analgesic activities. It may modulate hormone-related pathways and has potential to inhibit tumor cell proliferation. Nortracheloside enhances intestinal barrier function and reduces allergen permeation, suggesting immunoregulatory activity. Its diverse bioactivities make it of interest for developing therapeutic agents targeting inflammation and hormone-responsive cancers.
ln Vitro
Nortracheloside demonstrates anti-inflammatory activity by inhibiting LPS-induced nitric oxide production in mouse RAW264.7 cells. The compound has been shown to reduce allergen permeation and enhance intestinal barrier function in vitro. It exhibits antitumor and analgesic activities. These in vitro findings support its potential applications in inflammation research, food allergy research, and inflammatory bowel disease research.
ln Vivo
In vivo studies of Nortracheloside are limited as the compound is primarily used as a research chemical. Its anti-inflammatory and immunoregulatory properties suggest potential for in vivo evaluation in models of inflammatory bowel disease and food allergy. The compound's antitumor activity suggests possible applications in cancer research. However, comprehensive in vivo pharmacological studies specifically targeting Nortracheloside are not well documented. The compound is intended for research use only and is not for human therapeutic use.
Enzyme Assay
In vitro enzyme/receptor binding assays for Nortracheloside typically involve testing its anti-inflammatory activity in LPS-stimulated RAW264.7 macrophages. Cells are treated with varying concentrations of the compound and nitric oxide production is measured using the Griess assay. For intestinal barrier studies, epithelial cell monolayers are treated with the compound and permeability is assessed. The compound's purity (≥98%) and identity are confirmed using analytical chemistry methods such as nuclear magnetic resonance spectroscopy, high-performance liquid chromatography, and mass spectrometry.
Cell Assay
In vitro cell-based assays for Nortracheloside involve culturing RAW264.7 macrophages to evaluate its anti-inflammatory effects. Cells are treated with varying concentrations of the compound and stimulated with LPS; nitric oxide production is measured using the Griess assay. For intestinal barrier studies, epithelial cells are treated and barrier function is assessed by measuring transepithelial electrical resistance or permeability to fluorescent markers. Cell viability is assessed using MTT or similar colorimetric assays. All experiments are performed with appropriate controls.
Animal Protocol
In vivo animal experiments for Nortracheloside would be conducted to evaluate its anti-inflammatory and immunomodulatory activities. For inflammatory bowel disease studies, animal models of colitis would be used. For food allergy studies, sensitized animals would be treated and allergic responses assessed. Parameters assessed would include inflammatory markers, intestinal barrier function, and tissue histopathology. Control groups receiving vehicle alone would be included for comparison. All procedures would comply with institutional animal care and use committee guidelines.
ADME/Pharmacokinetics
The pharmacokinetic properties of Nortracheloside reflect its nature as a lignan glycoside. It has a molecular weight of 550.55 and the molecular formula C27H34O12. The compound is soluble in DMSO (125 mg/mL) for in vitro studies. As a glycoside, it may be metabolized by intestinal bacteria to the aglycone. Complete pharmacokinetic profiling including absorption, distribution, metabolism, and excretion would require further systematic studies using appropriate analytical methods such as high-performance liquid chromatography-mass spectrometry.
Toxicity/Toxicokinetics
The toxicity profile of Nortracheloside has been evaluated in the context of its use as a research chemical. As a naturally occurring lignan from Trachelospermum jasminoides, it is expected to have a favorable safety profile at research concentrations. Proper handling procedures including use of personal protective equipment are recommended when working with the compound. The compound is not approved for human therapeutic use and is intended for research purposes only. Long-term toxicity studies would be needed to fully establish its safety profile.
References

[1]. Lignans from Trachelospermum jasminoides. Planta Med. 2005 Jan;71(1):93-5.

Additional Infomation
According to reports, trachelospermum glycosides have been found in Trachelospermum jasminoides, Trachelospermum jasminoides, and other organisms with available data.
Nortracheloside (CAS# 33464-78-7) is a lignan isolated from Trachelospermum jasminoides (Lindl.) Lem. The compound exhibits anti-inflammatory, antitumor, and analgesic activities. Nortracheloside inhibits LPS-induced nitric oxide production in RAW264.7 cells and reduces allergen permeation while enhancing intestinal barrier function. It has potential for attenuating food allergy and inflammatory bowel disease through immunoregulatory bioactivity.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C26H32O12
Molecular Weight
536.53
Exact Mass
536.189
CAS #
33464-78-7
PubChem CID
45482323
Appearance
White to off-white solid powder
LogP
0.7
Hydrogen Bond Donor Count
6
Hydrogen Bond Acceptor Count
12
Rotatable Bond Count
9
Heavy Atom Count
38
Complexity
783
Defined Atom Stereocenter Count
7
SMILES
COC1=C(C=CC(=C1)C[C@H]2COC(=O)[C@@]2(CC3=CC(=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC)O)O
InChi Key
VXYKGOAXVHSLDD-PTHUBMCESA-N
InChi Code
InChI=1S/C26H32O12/c1-34-18-8-13(3-5-16(18)28)7-15-12-36-25(32)26(15,33)10-14-4-6-17(19(9-14)35-2)37-24-23(31)22(30)21(29)20(11-27)38-24/h3-6,8-9,15,20-24,27-31,33H,7,10-12H2,1-2H3/t15-,20+,21+,22-,23+,24+,26-/m0/s1
Chemical Name
(3S,4S)-3-hydroxy-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl]oxolan-2-one
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 125 mg/mL (232.98 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 10 mg/mL (18.64 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 100.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 10 mg/mL (18.64 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 100.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.8638 mL 9.3191 mL 18.6383 mL
5 mM 0.3728 mL 1.8638 mL 3.7277 mL
10 mM 0.1864 mL 0.9319 mL 1.8638 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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