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C20 Sphingomyelin (d18:1/20:0)

Item № 24450
CAS № 121999-68-6
Purity ≥98%
product image
                (CAS 121999-68-6)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     500 µg $294.00 0.00

Pricing updated 2019-07-23. Prices are subject to change without notice.

Description
Synonyms
  • N-eicosanoyl-D-erythro-Sphingosylphosphorylcholine
  • SM(d18:1/20:0)

C20 Sphingomyelin is a naturally occurring sphingolipid.1,2,3,4 Levels of C20 sphingomyelin are upregulated in the hippocampus of rats with diabetes induced by streptozotocin (Item No. 13104) and in human plasma where it is positively correlated with insulin resistance in obese humans.2 C20 sphingomyelin is also upregulated in the liver of a mouse model of Niemann-Pick type C1 disease, a neurodegenerative cholesterol-sphingolipid lysosomal storage disorder.1 The plasma concentration of C20 sphingomyelin is decreased in men with prostate cancer.3

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Technical Information
Formal Name
4-hydroxy-7S-[(1R,2E)-1-hydroxy-2-hexadecen-1-yl]-N,N,N-trimethyl-9-oxo-3,5-dioxa-8-aza-4-phosphaoctacosan-1-aminium, 4-oxide, inner salt
CAS Number
121999-68-6
Synonyms
  • N-eicosanoyl-D-erythro-Sphingosylphosphorylcholine
  • SM(d18:1/20:0)
Molecular Formula
C43H87N2O6P
Formula Weight
759.2
Purity
≥98%
Formulation
A solid
SMILES
O=C(CCCCCCCCCCCCCCCCCCC)N[C@@H](COP(OCC[N+](C)(C)C)([O-])=O)[C@H](O)/C=C/CCCCCCCCCCCCC
InChI Code
InChI=1S/C43H87N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-25-27-29-31-33-35-37-43(47)44-41(40-51-52(48,49)50-39-38-45(3,4)5)42(46)36-34-32-30-28-26-24-19-17-15-13-11-9-7-2/h34,36,41-42,46H,6-33,35,37-40H2,1-5H3,(H-,44,47,48,49)/b36-34+/t41-,42+/m0/s1
InChI Key
AADLTHQNYQJHQV-SVLGDMRNSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
Downloads & Resources
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Additional Information

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References & Product Citations
Product Description References

1. Praggastis, M., Tortelli, B., Zhang, J., et al. A murine Niemann-Pick C1 I1061T knock-in model recapitulates the pathological features of the most prevalent human disease allele J. Neurosci. 35(21), 8091-8106 (2015).

2. Hanamatsu, H., Ohnishi, S., Sakai, S., et al. Altered levels of serum sphingomyelin and ceramide containing distinct acyl chains in young obese adults Nutr. Diabetes 4, e141 (2014).

3. Awwad, H.M., Ohlmann, C.H., Stoeckle, M., et al. Choline-phospholipids inter-conversion is altered in elderly patients with prostate cancer Biochimie 126, 108-114 (2016).

4. Fiedorowicz, A., Prokopiuk, S., Zendzian-Piotrowska, M., et al. Sphingolipid profiles are altered in prefrontal cortex of rats under acute hyperglycemia Neuroscience 256, 282-291 (2014).

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