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860541P

Avanti

C8 Lactosyl(β) Ceramide (d18:1/8:0)

Avanti Polar Lipids 860541P, powder

Synonym(s):

D-lactosyl-β-1,1′ N-octanoyl-D-erythro-sphingosine

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About This Item

Empirical Formula (Hill Notation):
C38H71NO13
CAS Number:
384842-72-2
Molecular Weight:
749.97
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 5 mg (860541P-5mg)

manufacturer/tradename

Avanti Polar Lipids 860541P

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

[H][C@](/C=C/CCCCCCCCCCCCC)(O)[C@@]([H])(NC(CCCCCCC)=O)CO[C@H](O1)[C@H](O)[C@@H](O)[C@@H]([C@H]1CO)O[C@H](O2)[C@H](O)[C@@H](O)[C@H]([C@H]2CO)O

InChI

1S/C38H71NO13/c1-3-5-7-9-10-11-12-13-14-15-16-18-19-21-27(42)26(39-30(43)22-20-17-8-6-4-2)25-49-37-35(48)33(46)36(29(24-41)51-37)52-38-34(47)32(45)31(44)28(23-40)50-38/h19,21,26-29,31-38,40-42,44-48H,3-18,20,22-25H2,1-2H3,(H,39,43)/b21-19+/t26-,27+,28?,29?,31-,32?,33?,34?,35?,36+,37+,38-/m0/s1

InChI key

JUCWRRXMPGRQOG-WKSBFREFSA-N

General description

Lactosyl-ceramide is synthesized from complex glycosphingolipids by glucosylceramide synthase via caremide intermediate glucosylceramide.

Application

C8 Lactosyl(β) Ceramide (d18:1/8:0) is suitable for use as a substrate for endoglycoceramidase II. It is also suitable for use as a synthetic lipid standard for two-dimensional liquid chromatography−quadrupole time-of-flight mass spectrometry for lipid profiling and lipidomic analysis.

Biochem/physiol Actions

Lactosyl-β1-1′-N-octanoyl-D-erythro-sphingosine like other glycosphingolipids, stimulates caveolar endocytosis. C8-LacCer mediates clustering of β1-integrins and actin cytoskeleton reorganization in skin fibroblasts. High levels of lactosyl ceramide leads to decreased respiration leading to mitochondrial dysfunction.

Packaging

5 mL Amber Glass Screw Cap Vial (860541P-5mg)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A not-stop-flow online normal-reversed-phase two-dimensional liquid chromatography-quadrupole time-of-flight mass spectrometry method for comprehensive lipid profiling of human plasma from atherosclerosis patients
Li M, et al.
Journal of Chromatography A, 1372(3), 110-119 (2014)
The glycosphingolipid, lactosylceramide, regulates beta1-integrin clustering and endocytosis
Sharma DK, et al.
Cancer Research, 65(18), 8233-8241 (2005)
Lipidomic analysis of p-chlorophenylalanine-treated mice using continuous-flow two-dimensional liquid chromatography quadrupole time-of-flight mass spectrometry
Weng R, et al.
Rapid Communications in Mass Spectrometry, 29(16), 1491-1500 (2015)
Mass spectrometry-based identification of carbohydrate anomeric configuration to determine the mechanism of glycoside hydrolases
Shen YH, et al.
Carbohydrate Research, 476(3), 53-59 (2019)
Lactosylceramide contributes to mitochondrial dysfunction in diabetes
Novgorodov SA, et al.
Journal of Lipid Research, 57(4), 546-562 (2016)
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