Aldehydo-muramic acid
Basic information
- CAS
1114-41-6- Standard SMILES
C[C@@H](O[C@@H]([C@H](O)[C@H](O)CO)[C@@H](N)C=O)C(=O)O- InChIKey
ZZHZYDXMAKUKNS-OZRXBMAMSA-N- Molecular formula
- C9H17NO7
- Average molar mass
- 251.23 g/mol
- Monoisotopic mass
- 251.10050188
Overview
Aldehydo-muramic acid is a muramic acid. It is functionally related to an aldehydo-D-glucosamine.
Names & identifiers
- Preferred name
- Aldehydo-muramic acid
- IUPAC
- (2R)-2-[(2R,3R,4R,5R)-2-amino-4,5,6-trihydroxy-1-oxohexan-3-yl]oxypropanoic acid
- English name
- Muramic acid
- Molecular formula
- C9H17NO7
- Molecular weight
- 251.23
Names & synonyms
aldehydo-muramic acidCHEBI:479702-amino-3-O-[(1R)-1-carboxyethyl]-2-deoxy-aldehydo-D-glucose2-amino-3-O-((1R)-1-carboxyethyl)-2-deoxy-aldehydo-D-glucoseRefChem:936061GlyTouCan:G32865NFG32865NF(R)-2-(((2R,3R,4R,5R)-2-Amino-4,5,6-trihydroxy-1-oxohexan-3-yl)oxy)propanoic acidMFCD00213428Muramic acid, >=95%MURAMIC ACID [MI]SCHEMBL3424500
Show more names
Muramic acidMuramicAcid~99%(+)-MURAMIC ACIDMURAMIC ACID, (+)-aldehydo-muramicaciMURAMIC ACID, (+)-(RG)MURAMIC ACID USP/EP/BPMuramic acid hydrate,98%MURAMIC ACID HYDRATE 98%
UNII-D42T32747ZZZHZYDXMAKUKNS-OZRXBMAMSA-NDTXSID501366577EINECS 214-214-9AKOS040756263CS-W012632HY-W011916(2R)-2-[(1R,2R,3R)-1-[(1R)-1-amino-2-oxo-ethyl]-2,3,4-trihydroxy-butoxy]propanoic acid
Database identifiers
Properties
Computed structural properties
- XLogP
- -5.4
- Topological polar surface area
- 150 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 8
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 260
Physicochemical properties
- Melting point
- 140 · 140-150 °C (dec.)
- alpha
- 25 · D25 +103° (c = 0.26 in water) (Matsushima, Park); D22 +146° (6 minutes) +116° (31 hrs) (c = 0.57 in water) (Osawa, Jeanloz)
- Boiling point
- 592 · 592.0±50.0 °C(Predicted)
- Density
- 1.448 · 1.448±0.06 g/cm3(Predicted)
- Flash point
- 14 ℃ · 14℃
- storage temp.
- -20 °C · -20°C
- solubility
- Methanol (Slightly), Water (Slightly)
- form
- Solid
- pka
- 3.18 · 3.18±0.10(Predicted)
- color
- White to Light Brown
- optical activity
- 25 · [α]25/D 95 to 120°, c =0.26% (w/v) in water
- Water Solubility
- 20 mg/mL, · water: 20mg/mL, clear to very slightly hazy, colorless to faintly yellow
- Merck
- 13 · 13,6328
- BRN
- 1713780 · 1713780
- Stability
- Hygroscopic
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 3-10
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 1
- hs_code
- 2932990090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P280-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Applications
UsesAmino sugar found (as the N-acetyl derivative) in peptidoglycan, the main skeletal component of the bacterial cell wall. The N-acetyl derivative of muramic acid is an amino sugar that constitutes the peptidoglycan bacterial cell wall of Gram negative and Gram positive bacteria. Muramic acid is used as a chemical marker for the detection of bacterial contamination.
General DescriptionMuramic acid is a marker for Gram-positive bacteria.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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