CAS 131-48-6

Acetylneuraminic acid

Description:

Acetylneuraminic acid, commonly referred to as sialic acid, is a naturally occurring amino sugar and a derivative of neuraminic acid. It is characterized by its role as a crucial component of glycoproteins and glycolipids, particularly in the cell membranes of animals. This compound is known for its negative charge at physiological pH, which contributes to its biological functions, including cell recognition, signaling, and immune response modulation. Acetylneuraminic acid is typically found in high concentrations in tissues such as the brain and is involved in various biological processes, including pathogen recognition and the modulation of cellular interactions. Its structure features a nine-carbon backbone with an acetyl group, which enhances its solubility and stability. The presence of hydroxyl and amino groups allows for extensive hydrogen bonding, influencing its interactions with other biomolecules. Due to its significance in cellular communication and its potential implications in health and disease, acetylneuraminic acid is a subject of interest in biochemistry and medical research.

Formula: C₁₁H₁₉NO₉

InChI: InChI=1S/C11H19NO9/c1-4(14)12-8(5(15)2-6(16)11(20)21)10(19)9(18)7(17)3-13/h5,7-10,13,15,17-19H,2-3H2,1H3,(H,12,14)(H,20,21)/t5-,7+,8+,9+,10+/m0/s1

InChI key: InChIKey=KBGAYAKRZNYFFG-BOHATCBPSA-N

SMILES: [C@H]([C@H]([C@@H]([C@@H](CO)O)O)O)([C@H](CC(C(O)=O)=O)O)NC(C)=O

Synonyms:

• 5-N-Acetyl-<span class="text-smallcaps">D</span>-neuraminic acid
• 5-N-Acetyl-D-neuraminic acid
• 5-N-Acetylneuraminic acid
• <span class="text-smallcaps">D</smallcap>-glycero-<smallcap>D</span>-galacto-2-Nonulosonic acid, 5-(acetylamino)-3,5-dideoxy-
• <span class="text-smallcaps">D</smallcap>-glycero-<smallcap>D</span>-galacto-Nonulosonic acid, 5-acetamido-3,5-dideoxy-
• Aceneuramic acid
• Acetylneuraminic acid
• Acide N-acetylneuraminique
• D-glycero-D-galacto-2-Nonulosonic acid, 5-(acetylamino)-3,5-dideoxy-
• D-glycero-D-galacto-Nonulosonic acid, 5-acetamido-3,5-dideoxy-
• Lactaminic acid
• N-Acetyl-<span class="text-smallcaps">D</span>-neuraminic acid
• N-Acetyl-D-neuraminic acid
• N-Acetylneuramic acid
• N-Acetylneuraminsaure
• N-Acetylsialic acid
• N-acetylneuraminic acid
• Nana
• Ux 001
• acido N-acetilneuraminico
• 5-(acetylamino)-3,5-dideoxy-D-glycero-beta-D-galacto-non-2-ulopyranosonic acid
• 5-Acetamido-3,5-dideoxy-D-glycero-D-galactonulosonic acid
• (6xi)-5-(acetylamino)-3,5-dideoxy-beta-D-gluco-non-2-ulopyranosonic acid
• Galactononulosonic acid
• o-Sialic acid
• SialicAcid/N-acetylneuraminicacids
• Sialic Acid
• 5-(acetylamino)-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid
• 5-(acetylamino)-3,5-dideoxy-D-glycero-alpha-D-galacto-non-2-ulopyranosonic acid

N-acetyl-D-[1.2.3-13C3]neuraminic acid

CAS: 131-48-6

Ref: BE-MC-8241

N-Acetylneuraminic acid

CAS: 131-48-6

Ref: BE-BePure-21610

N-Acetylneuraminic Acid (NANA) extrapure, 98%

CAS: 131-48-6

Formula: C₁₁H₁₉NO₉

Purity: min. 99%

Color and Shape: White, Powder

Molecular weight: 309.28

Ref: SR-86419

N-Acetylneuraminic acid

CAS: 131-48-6

Formula: C₁₁H₁₉NO₉

Purity: 97.0%

Color and Shape: Solid

Molecular weight: 309.271

Ref: 10-F047790

N-Acetylneuraminic Acid-13C,d3

Controlled Product

CAS: 131-48-6

Stability Hygroscopic
Applications N-Acetylneuraminic Acid-13C,d3 is a labelled Neuraminic Acid derivative.
References Oetke, C., et al.: J. Biol. Chem., 277, 6688 (2002)

Formula: C₁₀₁₃CH₁₆D₃NO₉

Color and Shape: Neat

Molecular weight: 313.28

Ref: TR-A187009

N-Acetyl-D-[2,3-13C2]neuraminic Acid

Controlled Product

CAS: 131-48-6

Applications Carbon 13 labelled analogue of N-Acetylneuraminic acid (A187000).
References Methods Enzymol., 5, 391 (1962), Biochemistry, 18, 2086 (1979)

Formula: C₂C₉H₁₇NO₉

Color and Shape: Neat

Molecular weight: 309.239

Ref: TR-A187006

N-Acetylneuraminic Acid-15N1

Controlled Product

CAS: 131-48-6

Applications N-Acetylneuraminic Acid-15N1 is an isotope labelled analog of N-Acetylneuraminic Acid(A187000), which is a derivative of neuraminic acid.
References Methods Enzymol., 5, 391 (1962), Biochemistry, 18, 2086 (1979)

Formula: C₁₁H₁₉₁₅NO₉

Color and Shape: Neat

Molecular weight: 310.263

Ref: TR-A187001

N-Acetyl-D-[1-13C]neuraminic acid

CAS: 131-48-6

N-Acetyl-D-[1-13C]neuraminic acid is a monosialoganglioside that is synthesized in the human body. It is used to study the metabolic pathways of polysialic acid, which is a polysaccharide consisting of sialic acid and neuraminic acid. N-Acetyl-D-[1-13C]neuraminic acid has been shown to be effective in treating cancer and inflammatory disorders. In addition, it can be used as a diagnostic agent for glycan studies and diabetes neuropathy.

Formula: C₁₁H₁₉NO₉

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 309.27 g/mol

Ref: 3D-MA15642