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S0756

Sigma-Aldrich

Sphingomyelin

from chicken egg yolk, ≥95%

Synonym(e):

N-Acyl-4-sphingenyl-1-O-phosphorylcholine, N-Acyl-D-sphingosine-1-phosphocholine

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About This Item

CAS-Nummer:
85187-10-6
EG-Nummer:
286-097-2
MDL-Nummer:
MFCD00132361
UNSPSC-Code:
12352211
NACRES:
NA.25
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Biologische Quelle

chicken egg yolk

Qualitätsniveau

200

Assay

≥95%

Form

powder

Löslichkeit

chloroform/methanol: soluble 50 mg/mL, clear, colorless to faintly yellow (1:1)

Funktionelle Gruppe

phospholipid

Lipid-Typ

sphingolipids

Versandbedingung

ambient

Lagertemp.

−20°C

SMILES String

CCCCCCCCCCCCC/C=C/[C@H]([C@@H](NC=O)COP(O)(OCC[N+](C)(C)C)=O)O

InChI

1S/C24H49N2O6P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(28)23(25-22-27)21-32-33(29,30)31-20-19-26(2,3)4/h17-18,22-24,28H,5-16,19-21H2,1-4H3,(H-,25,27,29,30)/p+1/b18-17+/t23-,24+/m0/s1

InChIKey

LRYZPFWEZHSTHD-HEFFAWAOSA-O

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Allgemeine Beschreibung

Sphingomyelin (SM) is a principal sphingolipid in mammalian cell membranes. Its biological functions have been studied.[1]

Anwendung

Sphingomyelin is suitable for use:
  • in the preparation of standard during the enzymatic measurement of plasma sphingomyelin levels[2]
  • to study the binding of Vascular Anticoagulant α (VAC α) to planar phospholipid bilayers[3]
  • to perform fluorescence polarization of PC16 (N-[α-N-palmitoyl-ε-N-(4-nitrobenz-2-oxa-1,3-diazole)-L-lysine]-2-aminoethanol-N- (trimethylaminoethanol) phosphate) in dispersions of co-sonicated lecithin and sphingomyelin[4]
  • for reconstitution of viral ion channel protein M2 into liposomes[5]
  • as a standard sample to define spectral fingerproint using Time-of-flight secondary ion mass spectrometry (ToF-SIMS)[6]
  • to evaluate the contribution of various phospholipids to the formation of foam in the amniotic fluid[7]

Biochem./physiol. Wirkung

Sphingomyelin is the second most abundant lipid and major sphingolipid component of HDL and the plasma membrane. It forms cholesterol-enriched lipid rafts. It has a key role in the availability of plasma membrane-free cholesterol.[8]

Qualität

Contains primarily palmitic acid.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
0000417443
0000417443
0000394834
0000374060
0000374062

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Die Dokumentenbibliothek aufrufen

Biological functions of sphingomyelins.
Slotte JP.
Progress in Lipid Research, 52(4), 424-437 (2013)
D E Freer et al.
Clinical chemistry, 24(11), 1980-1984 (1978-11-01)
We evaluated the relative contributions of various phospholipids to the formation of foam in the amniotic fluid "foam stability test", by use of an artificial system of saline, ethanol, and dipalmitoyl 3-sn-phosphatidylcholine to determine the relationship between dipalmitoyl 3-sn-phosphatidylcholine concentration
H A Andree et al.
The Journal of biological chemistry, 265(9), 4923-4928 (1990-03-25)
Vascular anticoagulant alpha (VAC alpha, annexin V) is a member of the family of calcium and phospholipid binding proteins, the annexins. The binding properties of VAC alpha to phospholipid bilayers were studied by ellipsometry. Adsorption was calcium-dependent and completely reversible
Mohammad Reza Hojjati et al.
Journal of lipid research, 47(3), 673-676 (2005-12-24)
Sphingomyelin (SM) and phosphatidylcholine (PC) are two major phospholipids on plasma lipoproteins. Their concentration is classically measured by lipid extraction, thin-layer chromatography, and phosphate determination on separated SM or PC spots. Here, we describe two rapid, specific, and sensitive enzymatic
J C Russell
Clinical chemistry, 33(7), 1177-1184 (1987-07-01)
The mechanism of a new fluorescence polarization method for measuring phospholipid in amniotic fluid is described. The fluorescence polarization of a surfactant fluorescent dye solubilized in amniotic fluid correlates significantly with the L/S ratio. Model studies indicate that this results
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Protokolle

LC/MS Analysis of Phospholipids in Milk on Asc

(soybean), ≥97%; L-α-Phosphatidylethanolamine from egg yolk, Type III, ≥97% (TLC), lyophilized powder; L-α-Phosphatidylcholine, from egg yolk, Type XVI-E, ≥99% (TLC), lyophilized powder; Sphingomyelin, from chicken egg yolk, ≥95%

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 Antwort

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 Antwort

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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