Glucosamine (USAN:INN:NF)
Basic information
- CAS
3416-24-8- Standard SMILES
NC1C(O)[C@@H](O)C(CO)O[C@@H]1O- InChIKey
MSWZFWKMSRAUBD-GQNBSWLHSA-N- Molecular formula
- C6H13NO5
- Average molar mass
- 179.17 g/mol
- Monoisotopic mass
- 179.07937252
Overview
See also: D-Glucosamine (annotation moved to).
Names & identifiers
- Preferred name
- Glucosamine (USAN:INN:NF)
- IUPAC
- (2S,5R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol
- English name
- Glucosamine
- Molecular formula
- C6H13NO5
- Molecular weight
- 179.17
Names & synonyms
Glucosamine (USAN:INN:NF)Glucosamine [USAN:INN:NF]RefChem:938001GlyTouCan:G25972NYG25972NY2-amino-2-deoxyglucoseGlucosaminum [INN-Latin]Glucosamina [INN-Spanish]Glucose, 2-amino-2-deoxy-Viartril-SHSDB 7469EINECS 222-311-2
Show more names
D-GLUCOSAMINEaminoglucose2-amino-2-deoxy-d-glucose2-amino-2-deoxy-d-glucosGLUCOSAMINEGlucosamine 13C6D-(+)-Glucosamine hySYNTHETICGLUCOSAMINEPropyl N-Acetyl-βGlucosamine USP/EP/BP
UNII-N08U5BOQ1KSCHEMBL12968986MSWZFWKMSRAUBD-GQNBSWLHSA-N2B4D44B2-D5AC-4DA4-9BE6-A4AE9574E4A6
Database identifiers
- CAS
3416-24-8- PubChem CID
- 18897
Properties
Computed structural properties
- XLogP
- -2.8
- Topological polar surface area
- 116 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 1
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 155
Physicochemical properties
- Boiling point
- 311.69 °C · 311.69°C (rough estimate)
- Density
- 1.3767 · 1.3767 (rough estimate)
- refractive index
- 1.424 · 1.4240 (estimate)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- 23 · DMSO:23.0(Max Conc. mg/mL);128.37(Max Conc. mM)Water:36.0(Max Conc. mg/mL);200.93(Max Conc. mM)
- form
- Solid
- pka
- 8.04 · pKa 8.04(H2O,t = 15.5,I=0.00,N2)(Approximate)
- Melting point
- 88 °C · 88 °C
- color
- White to Off-White
- optical activity
- 100 · α form +100 → +72(HCl) β form +28 → +47.5
- Henry's Law Constant
- 1.3 · 1.3×1010 mol/(m3Pa) at 25℃, HSDB (2015)
- Cosmetics Ingredients Functions
- ANTISTATICHAIR CONDITIONING
- Cosmetic Ingredient Review (CIR)
- Glucosamine (3416-24-8)
- InChI
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
- tsca
- TSCA listed
- Hazardous Substances Data
- 3416-24-8(Hazardous Substances Data)
Chemistry & industry
Applications
OccurrenceGlucosamine is found in mucopolysaccharides, chitin, and mucoproteins. Glucosamine is a naturally occurring substance; glucosamine sulfate is manufactured synthetically.
UsesGlucosamine is an amino sugar that can regulate growth factor gene transcription. It is also widely touted as remedy for osteoarthritis (OA).
UsesPharmaceutic aid.
Preparation methods
PreparationGlucosamine can be prepared from shrimp exoskeletons[1].
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: The open-chain form of D-glucosamine.
Suppliers
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Related reactions
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Compound notes
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