Basic information
- CAS
131-48-6- Standard SMILES
CC(=O)NC1C(O)C[C@@](O)(C(=O)O)OC1C(O)C(O)CO- InChIKey
SQVRNKJHWKZAKO-RASJKGJYSA-N- Molecular formula
- C11H19NO9
- Average molar mass
- 309.27 g/mol
- Monoisotopic mass
- 309.10598118
Overview
See also: N-Acetyl-alpha-D-neuraminic acid (annotation moved to); Aceneuramic Acid (annotation moved to); N-Acetyl-Neuraminic Acid (annotation moved to).
Names & identifiers
- Preferred name
- GlyTouCan:G31630FD
- IUPAC
- (2S)-5-acetamido-2,4-dihydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
- English name
- N-Acetylneuraminic acid
- Molecular formula
- C11H19NO9
- Molecular weight
- 309.27
Names & synonyms
RefChem:701637GlyTouCan:G31630FDG31630FD131-48-6SIALIC ACIDNEU5ACNANNANAAcetylneuraminic acidNeuAcLACTAMINIC ACID(-)-N-ACETYLNEURAMINIC ACID
Show more names
(2S,4S,5R,6R)-5-AcetaMido-2,4-dihydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acidN-AcetyIneuraminic acid
Database identifiers
- CAS
131-48-6- PubChem CID
- 124040735
- EC Number
- 205-023-1
Properties
Computed structural properties
- XLogP
- -3.5
- Topological polar surface area
- 177 Ų
- Hydrogen bond donors
- 7
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 5
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 403
Physicochemical properties
- Melting point
- 184 · 184-186 °C
- alpha
- -32 · -32 º (c=2,water)
- Boiling point
- 449.56 °C · 449.56°C (rough estimate)
- Density
- 1.358 · 1.3580 (rough estimate)
- refractive index
- -32 ° · -32 ° (C=1, H2O)
- storage temp.
- -20 °C · -20°C
- solubility
- 50 g/L · 50 g/L (20°C)
- pka
- 2.41 · 2.41±0.54(Predicted)
- form
- synthetic, crystalline
- color
- White to Off-White
- biological source
- synthetic
- optical activity
- -32 · -32
- Water Solubility
- 50 g/L · 50 g/L (20 ºC)
- Sensitive
- Air Sensitive
- Merck
- 14 · 14,8484
- BRN
- 1716283 · 1716283
- Stability
- Stable. Incompatible with strong oxidizing agents.
- Major Application
- food and beverages
- Cosmetics Ingredients Functions
- SKIN CONDITIONINGSKIN PROTECTING
- 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)/t5-,6+,7+,8+,9+,11-/m0/s1
- InChIKey
- SQVRNKJHWKZAKO-PFQGKNLYSA-N
- SMILES
- O[C@@]1(O[C@@]([C@@H]([C@H](C1)O)NC(C)=O)([H])[C@@H]([C@@H](CO)O)O)C(O)=O
- LogP
- -1.897 · -1.897 (est)
- CAS DataBase Reference
- 131 · 131-48-6(CAS DataBase Reference)
- NCI Dictionary of Cancer Terms
- sialic acid
- FDA UNII
- 2782 OP0 · GZP2782OP0
- ATC code
- 9 AX05 · M09AX05
- EPA Substance Registry System
- Neuraminic acid, N-acetyl- (131-48-6)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 79 · NA.79
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 319 · H319
- Precautionary statements
- 264 · P264-P280-P305+P351+P338-P337+P313
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 22 · 22-24/25-36-26
- WGK Germany
- 3 · 3
- F
- 3 · 3-10-23
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29329970 · 29329970
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 · Eye Irrit. 2
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory InformationNeuraminic acid, N-acetyl-: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- F
- 3-10-23
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29329970
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 22-24/25-36-26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H319
- Hazard Classifications
- Eye Irrit. 2
- Precautionary statements
- P264-P280-P305+P351+P338-P337+P313
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationNeuraminic acid, N-acetyl-: ACTIVE
Applications
DescriptionN-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.
UsesN-Acetylneuraminic acid is an integral part of sialic acids (SAs), important functional sugars that play an important role in maintaining and improving brain health, detoxification, antibacterial, and immune enhancement. n-Acetylneuraminic acid is biologically useful for neurotransmission, leukocyte extravasation, viral or bacterial infection, and carbohydrate-protein recognition. n- Acetylneuraminic acid is used to study its biochemistry, metabolism and absorption in vivo and in vitro.
Suppliers100 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
山东雨禾医药科技有限公司15263077727
T&W GROUP021-61551611 13296011611 · [email protected]
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张家港市思普生化有限公司512-0512-58992291,58992287 18606280718 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
南京春秋生物工程有限公司17388075642 13815430202 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
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艾科试剂4008-755-333 18080918076 · [email protected]
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赛默飞世尔科技（中国）有限公司800-810-5118 · [email protected]
上海遐瑞医药科技有限公司+86 21 61551611
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Additional notes
DefinitionChEBI: N-Acetylneuraminic acid is n-Acetylneuraminic acid with beta configuration at the anomeric centre. It has a role as an epitope. It is functionally related to a beta-neuraminic acid. It is a conjugate acid of a N-acetyl-beta-neuraminate.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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