3D Mol Similar

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+

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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:?Xi
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

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6. NMR Spectrum

13C NMR : in D2O

1H NMR : 400 MHz in DMSO-d6

IR : KBr disc

IR : nujol mull

Mass

7. Synthesis Route

131-48-6Total: 4 Synthesis Route

72-87-7 2 Suppliers

312-85-6 73 Suppliers

131-48-6 285 Suppliers

Literatures:
Xu, Ping; Qiu, Jian Hua; Zhang, Yi Nan; Chen, Jing; Wang, Peng George; Yan, Bing; Song, Jing; Xi, Ri Mo; Deng, Zi Xin; Ma, Cui Qing Advanced Synthesis and Catalysis, 2007 , vol. 349, # 10 p. 1614 - 1618
Yield: null

50-99-7 475 Suppliers

7512-17-6 331 Suppliers

131-48-6 285 Suppliers

Literatures:
Bioscience, Biotechnology and Biochemistry, , vol. 69, # 10 p. 1944 - 1950
Yield: null

7512-17-6 331 Suppliers

57-60-3

131-48-6 285 Suppliers

Literatures:
Bioscience, Biotechnology and Biochemistry, , vol. 69, # 10 p. 1944 - 1950
Yield: null

View all

8. Precursor and Product

precursor:

57-60-3

72-87-7

328-42-7

7512-17-6

50-99-7

312-85-6

product :

3615-17-6

57-60-3

127-17-3

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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