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SMB00933

Sigma-Aldrich

2′-Fucosyllactose

≥95% (NMR)

Synonym(s):

2′-Fucosyllactose, 2′-Ο-Fucosyllactose

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About This Item

Empirical Formula (Hill Notation):
C18H32O15
CAS Number:
Molecular Weight:
488.44
UNSPSC Code:
12352201
NACRES:
NA.25

Pricing and availability is not currently available.

biological source

milk

Quality Level

assay

≥95% (NMR)

form

crystalline powder

mol wt

488.44 g/mol

storage condition

(Keep container tightly closed in a dry and well -ventilated place.)

color

white

mp

230 - 231 °C ((446 - 448 °F ))

storage temp.

-10 to -25°C

SMILES string

O1[C@H]([C@H]([C@@H]([C@@H]([C@@H]1C)O)O)O)O[C@H]2[C@@H](O[C@@H]([C@@H]([C@@H]2O)O)CO)O[C@@H]([C@H](O)[C@@H](O)C=O)[C@H](O)CO

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1 of 4

This Item
1628007PHR157746826
manufacturer/tradename

EDQM

manufacturer/tradename

USP

manufacturer/tradename

-

manufacturer/tradename

-

application(s)

pharmaceutical (small molecule)

application(s)

pharmaceutical (small molecule)

application(s)

pharmaceutical (small molecule)

application(s)

clinical testing

format

neat

format

neat

format

neat

format

neat

API family

sulfamerazine

API family

sulfamerazine

API family

sulfamerazine

API family

-

storage temp.

2-8°C

storage temp.

-

storage temp.

2-30°C

storage temp.

-

General description

2′-Fucosyl-D-lactose (2′-FL) is a naturally occurring disaccharide, categorized as a fucose-containing oligosaccharide. It serves as a substrate for the identification, differentiation, and characterization of fucosidases. Additionally, it finds utility in biosensor development for the recognition of anti-infective oligosaccharides and the differentiation of IL-8 receptor specificity and function. Existing research indicates that 2′-FL may possess various biological activities, including immunomodulatory, anti-inflammatory, anti-microbial, and anti-cancer properties.

Notably, it holds the distinction of being the most abundant human milk oligosaccharide (HMO), contributing to multiple functions, including acting as a prebiotic, safeguarding against infections and inflammation, modulating the immune system, supporting brain development, and reducing the risk of necrotizing enterocolitis. Also, high levels of 2′-fucosyllactose is associated with excessive weight gain during exclusive breastfeeding in 0 to 5 months infants. HMOs are important metabolites regulating host′s innate immune response.

Application

2′-Fucosyllactose is a versatile compound and a biomarker that finds application in microbiome, metabolomics, biochemical and nutrition research.

Biochem/physiol Actions

2′-Fucosyllactose plays a role in modulating CD14 expression, providing relief in colitis, and influencing the composition of the gut microbiome. Its impact extends to stimulating T cells, leading to heightened IFN-γ production, while concurrently reducing the production of cytokines IL-6, IL-17, and TNF-α.

Features and Benefits

  • High-purity compound suitable for a wide variety of research applications

Other Notes

For additional information on our range of Biochemicals, please complete this form.
To gain a comprehensive understanding of our extensive range of Disaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Ling Xiao et al.
Frontiers in immunology, 9, 452-452 (2018-03-30)
Human milk is uniquely suited to provide optimal nutrition and immune protection to infants. Human milk oligosaccharides are structural complex and diverse consisting of short chain and long chain oligosaccharides typically present in a 9:1 ratio. 2'-Fucosyllactose (2'FL) is one
Melanie W Larsson et al.
Frontiers in pediatrics, 7, 297-297 (2019-08-06)
Background: Some infants experience excessive weight gain during exclusive breastfeeding. The cause is unknown, but variation in human milk composition might play a role. Several human milk koligosaccharides (HMOs) have been associated with growth velocity in breastfed infants, and it
Ignasi Azagra-Boronat et al.
Cells, 8(8) (2019-08-14)
Colonization of the gut in early life can be altered through multiple environmental factors. The present study aimed to investigate the effects of 2'-fucosyllactose (2'-FL), a mixture of short-chain galactooligosaccharides/long-chain fructooligosaccharides (scGOS/lcFOS) 9:1 and their combination (scGOS/lcFOS/2'-FL) on dysbiosis induced

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