A sialic acid
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Product Type

Biochemicals

Research Area

Cancer
Tumor Microenvironment

N-Glycolylneuraminic Acid

Item No. 30283

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(2-hydroxyacetyl)-neuraminic acid
CAS Number
1113-83-3
Synonyms
  • Neu5Gc
  • N-glycolyl-Neuraminic Acid
Molecular Formula
C11H19NO10
Formula Weight
325.3
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 10 mg/ml
SMILES
OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](NC(CO)=O)[C@@H](O)CC(C(O)=O)=O
InChi Code
InChI=1S/C11H19NO10/c13-2-6(17)9(19)10(20)8(12-7(18)3-14)4(15)1-5(16)11(21)22/h4,6,8-10,13-15,17,19-20H,1-3H2,(H,12,18)(H,21,22)/t4-,6+,8+,9+,10+/m0/s1
InChi Key
SUHQNCLNRUAGOO-KQCZLNONSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $69

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    50 mg

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    100 mg

    $461

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    250 mg

    $983

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    Cayman Chemical
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    Product Description

    N-Glycolylneuraminic acid (Neu5Gc) is a sialic acid that is found in non-human primate tissues.1,2 It is not endogenously produced in humans due to a mutation in the gene that encodes CMP-Neu5Ac hydroxylase, the enzyme that hydrolyzes N-acetylneuraminic acid to form Neu5Gc, but accumulates in human cells after exogenous ingestion from dietary sources such as red meat and dairy products. Neu5Gc accumulates in human tumors, including retinoblastomas, melanomas, colon carcinomas, and breast cancer, and Neu5Gc uptake is enhanced under hypoxic conditions.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nguyen, D.H., Tangvoranuntakul, P., and Varki, A. Effects of natural human antibodies against a nonhuman sialic acid that metabolically incorporates into activated and malignant immune cells. J. Immunol. 175(1), 228-236 (2005).

    2. Hedlund, M., Padler-Karavani, V., Varki, N.M., et al. Evidence for a human-specific mechanism for diet and antibody-mediated inflammation in carcinoma progression. Proc. Natl. Acad. Sci. USA 105(48), 18936-18941 (2008).