Physicochemical Properties
Molecular Formula | C18H32O15 |
Molecular Weight | 488.44 |
Exact Mass | 488.174 |
CAS # | 41263-94-9 |
PubChem CID | 170484 |
Appearance | White to off-white solid powder |
Density | 1.68g/cm3 |
Boiling Point | 902.2ºC at 760 mmHg |
Melting Point | 230-231 °C |
Flash Point | 311.9ºC |
Vapour Pressure | 0mmHg at 25°C |
Index of Refraction | 1.631 |
LogP | -6.1 |
Hydrogen Bond Donor Count | 10 |
Hydrogen Bond Acceptor Count | 15 |
Rotatable Bond Count | 10 |
Heavy Atom Count | 33 |
Complexity | 609 |
Defined Atom Stereocenter Count | 14 |
SMILES | C[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)O[C@@H]2[C@H]([C@H]([C@H](O[C@H]2O[C@H]([C@@H](CO)O)[C@@H]([C@H](C=O)O)O)CO)O)O)O)O)O |
InChi Key | HWHQUWQCBPAQQH-BWRPKUOHSA-N |
InChi Code | InChI=1S/C18H32O15/c1-5-9(24)12(27)14(29)17(30-5)33-16-13(28)11(26)8(4-21)31-18(16)32-15(7(23)3-20)10(25)6(22)2-19/h2,5-18,20-29H,3-4H2,1H3/t5-,6-,7+,8+,9+,10+,11-,12+,13-,14-,15+,16+,17-,18-/m0/s1 |
Chemical Name | (2R,3R,4R,5R)-4-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanal |
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) |
Biological Activity
Targets | Target: IFN-γ, IL-6, IL-17, and TNF-α[1] |
ln Vitro | In T84 cells, 2'-Fucosyllactose (2'-FL; 0–12 mg/mL; 48 h) attenuates LPS (100 μg/mL) and stimulates IL-8 secretion while suppressing cell-associated CD14 expression[1]. In T84 and HCT8 cells, 2'-Fucosyllactose (2 mg/mL; 48 h) reduces inflammation brought on by bacterial invasion. Inhibiting ETEC invasion and reducing the ensuing IL-8 release are the two effects of 2'-fucosyllactose[1]. In T84 and HCT8 cells, 2'-fucosyllactose (2 mg/mL; 48 h) activates signal pathways for macrophage migration inhibitory factor, which reduces inflammation[1]. |
ln Vivo | 2'-Fucosyllactose (2'-FL; 100 mg (200 μL); ig; daily, for 4 d; C57BL/6 mice with AIEC infection) reduces inflammation and AIEC infection in vivo[1]. |
Cell Assay |
Western Blot Analysis[1] Cell Types: T84 cells Tested Concentrations: 0, 2, and 4 mg/mL Incubation Duration: 48 hrs (hours) Experimental Results: Suppressed CD14 mRNA and decreased cell-associated CD14 protein expression. Western Blot Analysis[1] Cell Types: T84 and HCT8 cellsT84 and HCT8 cells Tested Concentrations: 2 mg/mL Incubation Duration: 48 hrs (hours) Experimental Results: Suppressed CD14 mRNA and decreased cell-associated CD14 protein expression. Inhibited CD14 and NF-κB induction. Induced iκB and SOCS2 expression and STAT3 phosphorylation. |
Animal Protocol |
Animal/Disease Models: C57BL/6 mice (8 weeks) with AIEC (uropathogenic E. coli, and adherent-invasive E. coli) infection[1] Doses: 100 mg (200 μL) Route of Administration: po (oral gavage); daily, for 4 days Experimental Results: Had colons lengths were closer to normal. Inhibited the colonization of the colonic mucosa by O83-positive bacteria. diminished CD14 expression, CD14 mRNA levels, IL-6, IL-17 and TNF -α levels in colonic. |
References |
[1]. The human milk oligosaccharide 2'-fucosyllactose modulates CD14 expression in human enterocytes, thereby attenuating LPS-induced inflammation. Gut. 2016 Jan;65(1):33-46. [2]. Human milk--derived oligosaccharides and plant-derived oligosaccharides stimulate cytokine production of cord blood T-cells in vitro. Pediatr Res. 2004 Oct;56(4):536-40. |
Additional Infomation | 2'-Fucosyllactose is under investigation in clinical trial NCT03847467 (Pilot and Feasibility Study of 2'-FL as a Dietary Supplement in IBD Patients Receiving Stable Maintenance Anti-tnf Therapy). |
Solubility Data
Solubility (In Vitro) | H2O : 50 mg/mL (102.37 mM) |
Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 :Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300:Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.) |
Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
1 mM | 2.0473 mL | 10.2367 mL | 20.4733 mL | |
5 mM | 0.4095 mL | 2.0473 mL | 4.0947 mL | |
10 mM | 0.2047 mL | 1.0237 mL | 2.0473 mL |