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Home> Encyclopedia >Enzymes>Pharmaceutical Intermediates>Organic Intermediate
N-Acetylneuraminic acid structure
N-Acetylneuraminic acid structure

N-Acetylneuraminic acid

Iupac Name:5-acetamido-2,4-dihydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
CAS No.: 131-48-6
Molecular Weight:309.27000
Modify Date.: 2023-02-09 13:17
Introduction: Carbon 13 labelled analogue of N-Acetylneuraminic acid (A187000). View more+
1. Names and Identifiers
1.1 Name
N-Acetylneuraminic acid
1.2 Synonyms

(4S,5R,6R,7S,8R)-5-Acetamido-4,6,7,8,9-pentahydroxy-2-oxononanoic acid (4ξ)-5-Acetamido-3,5-dideoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]-L-glycero-hex-2-ulopyranosonic acid 5-(Acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic Acid 5-(acetylamino)-3,5-dideoxy-D-glycero-D-galacto-non-2-ulosonic acid 5-(acetylamino)-3,5-dideoxy-Δ-glycero-Δ-galacto-2-Nonulosonic acid 5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-non-2-ulosonic acid 5-Acetamido-3,5-dideoxy-D-glycero-D-galactononulosonic acid 5-Acetamido-3,5-dideoxy-D-glycero-D-galactononulosonic acid,Lactaminic acid,NAN Aceneuramic acid D-arabino-2-Nonulopyranosonic acid, 5-(acetylamino)-3,5-dideoxy- D-glycero-D-galacto-2-Nonulosonic acid, 5-(acetylamino)-3,5-dideoxy- EINECS 205-023-1 Lactaminic acid MFCD00006620 N-acetyl-D-neuraminic acid NAN NANA NANA H2O NANA TYPE IV-S NANA TYPE VI NEU5AC O-SIALIC ACID sialic acid sialic acid powder Sialomucin

1.3 CAS No.
131-48-6
1.4 CID
906
1.5 EINECS(EC#)
205-023-1
1.6 Molecular Formula
C11H19NO9 (isomer)
1.7 Inchi
InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)
1.8 InChkey
SQVRNKJHWKZAKO-UHFFFAOYSA-N
1.9 Canonical Smiles
CC(=O)NC1C(CC(OC1C(C(CO)O)O)(C(=O)O)O)O
1.10 Isomers Smiles
CC(=O)NC1C(CC(OC1C(C(CO)O)O)(C(=O)O)O)O
2. Properties
2.1 Density
1.727 g/cm3
2.1 Melting point
184-186°C (dec.)(lit.)
2.1 Boiling point
395.6oC at 760 mmHg
2.1 Refractive index
-32 ° (C=1, H2O)
2.1 Flash Point
193oC
2.1 Precise Quality
309.10600
2.1 PSA
176.78000
2.1 logP
-3.48090
2.1 Solubility
Water : 50 g/L (20°C)
2.2 Appearance
Crystalline
2.3 Storage
Store at -20°C. Air Sensitive.
2.4 Chemical Properties
N-acetylneuraminic acid is an N-acyl derivative of neuraminic or acid amino sugar derivative, derived from N-acetylmannosamine and pyruvic acid. It is an important constituent of glycoproteins and glycolipids. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria.
2.5 Physical Properties
The numbering of the sialic acid structure begins at the carboxylate carbon and continues around the chain. The configuration which places the carboxylate in the axial position is the alpha-anomer. The alpha-anomer is the form that is found when sialic acid is bound to glycans, however, in solution it is mainly (over 90 %) in the beta-anomeric form. A bacterial enzyme with sialic acid mutarotase activity, NanM, has been discovered which is able to rapidly equilibrate solutions of sialic acid to the resting equilibrium position of around 90 % beta 10 % alpha.
2.6 pKa
2.41±0.54(Predicted)
2.7 Water Solubility
50 g/L (20 oC)
2.8 Stability
Stable. Incompatible with strong oxidizing agents.
2.9 StorageTemp
?20°C
3. Use and Manufacturing
3.1 Usage
Carbon 13 labelled analogue of N-Acetylneuraminic acid (A187000).
4. Safety and Handling
4.1 Hazard Codes
Xi
4.1 Risk Statements
R36/37/38
4.1 Safety Statements
S22-S24/25
4.1 RIDADR
NONH for all modes of transport
4.1 WGK Germany
3
4.1 Safety

Hazard Codes:?IrritantXi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-36-26
S22: Do not breathe dust.?
S24/25: Avoid contact with skin and eyes.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36: Wear suitable protective clothing.
WGK Germany: 3
F:?3-10-23
Hazard Note:?Irritant

4.2 Sensitive
Air Sensitive
4.3 Specification

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media: In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam.?
Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage: Store N-Acetylneuraminic Acid (CAS NO.131-48-6) in a cool, dry place. Keep container closed when not in use. Deep freeze (below -20°C). Keep refrigerated. (Store below 4°C/39°F.)

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s) No symbol.
Signal word

No signal word.

Hazard statement(s)

none

Precautionary statement(s)
Prevention

none

Response

none

Storage

none

Disposal

none

2.3 Other hazards which do not result in classification

none

9. Other Information
9.0 Usage
N-Acetylneuraminic acid is useful biologically in neurotransmission, leukocyte extravasation, viral or bacterial infections and carbohydrate-protein recognition. Neu5Ac is used to study its biochemistry, metabolism and uptake in vivo and in vitro. Neu5Ac is used in the development of nanocarriers.
10. Computational chemical data
  • Molecular Weight: 309.27000g/mol
  • Molecular Formula: C11H19NO9
  • Compound Is Canonicalized: True
  • XLogP3-AA: -3.5
  • Exact Mass: 309.10598118
  • Monoisotopic Mass: 309.10598118
  • Complexity: 403
  • Rotatable Bond Count: 5
  • Hydrogen Bond Donor Count: 7
  • Hydrogen Bond Acceptor Count: 9
  • Topological Polar Surface Area: 177
  • Heavy Atom Count: 21
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 6
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADceByPAAAAAAAAAAAAAAAAAAAAAAAAAAkAAAAAAAAAAAAAAAAHgAQCAAACDzhgAYCCALABgAIAAGQGAIAAAAAAAAAAIFIAAATEBIAgAQHQAAHFgCXAAH6+aeQAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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