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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:44:10 UTC
Update Date2023-02-21 17:20:54 UTC
HMDB IDHMDB0031581
Secondary Accession Numbers
  • HMDB31581
Metabolite Identification
Common NameMorpholine
DescriptionMorpholine is a permitted (FDA) in edible coatings for fruit and vegetables. Morpholine is a food contaminant arising from its use as a boiler water additive Morpholine is a common additive, in ppm concentrations, for pH adjustment in both fossil fuel and nuclear power plant steam systems. Morpholine is used because its volatility is about the same as water, so once it is added to the water, its concentration becomes distributed rather evenly in both the water and steam phases. Its pH adjusting qualities then become distributed throughout the steam plant to provide corrosion protection. Morpholine is often used in conjunction with low concentrations of hydrazine or ammonia to provide a comprehensive all-volatile treatment chemistry for corrosion protection for the steam systems of such plants. Morpholine decomposes reasonably slowly in the absence of oxygen even at the high temperatures and pressures in these steam systems. Morpholine is an organic chemical compound having the chemical formula O(CH2CH2)2NH. This heterocycle, pictured at right, features both amine and ether functional groups. Because of the amine, morpholine is a base; its conjugate acid is called morpholinium. For example, when morpholine is neutralized by hydrochloric acid, one obtains the salt morpholinium chloride. Morpholine is widely used in organic synthesis. For example, it is a building block in the preparation of the antibiotic linezolid and the anticancer agent gefitinib (Iressa)
Structure
Thumb
Synonyms
Chemical FormulaC4H9NO
Average Molecular Weight87.1204
Monoisotopic Molecular Weight87.068413915
IUPAC Namemorpholine
Traditional Namemorpholine
CAS Registry Number110-91-8
SMILES
C1COCCN1
InChI Identifier
InChI=1S/C4H9NO/c1-3-6-4-2-5-1/h5H,1-4H2
InChI KeyYNAVUWVOSKDBBP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as morpholines. These are organic compounds containing a morpholine moiety, which consists of a six-member aliphatic saturated ring with the formula C4H9NO, where the oxygen and nitrogen atoms lie at positions 1 and 4, respectively.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxazinanes
Sub ClassMorpholines
Direct ParentMorpholines
Alternative Parents
Substituents
  • Morpholine
  • Oxacycle
  • Azacycle
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Dialkyl ether
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-4.9 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
LogP-0.86Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB13669
Phenol Explorer Compound IDNot Available
FooDB IDFDB008207
KNApSAcK IDC00014903
Chemspider ID13837537
KEGG Compound IDC14452
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMorpholine
METLIN IDNot Available
PubChem Compound8083
PDB IDNot Available
ChEBI ID34856
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kubis A, Witek R, Baran E, Jadach W, Matecka K, Zaba A: [In vivo antimycotic effect of topically applied morpholine (author's transl)]. Pharmazie. 1981 Jun;36(6):429-31. [PubMed:7279992 ]
  2. Hay RJ: Antifungal drugs on the horizon. J Am Acad Dermatol. 1994 Sep;31(3 Pt 2):S82-6. [PubMed:8077515 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .