Record Information
Version1.0
Creation date2010-04-08 22:12:44 UTC
Update date2019-11-26 03:13:58 UTC
Primary IDFDB016934
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePolyethylene glycol
DescriptionDiluent in colour additive mixts. for colouring shell eggs; coating, binder, plasticising agent and/or lubricant in tablets used for food; adjuvant to improve flavour and as a bodying agent in non-nutritive sweeteners; adjuvant in dispersing vitamin preparations; defoaming agent; boiler-water additive, etc. Depending on the catalyst type, the mechanism of polymerization can be cationic or anionic. The anionic mechanism is preferable because it allows one to obtain PEG with a low polydispersity. Polymerization of ethylene oxide is an exothermic process. Overheating or contaminating ethylene oxide with catalysts such as alkalis or metal oxides can lead to runaway polymerization which can end with an explosion after few hours.; PEG is a popular precipitant for protein crystallization, X-ray diffraction of protein crystals can reveal the atomic structure of proteins.; PEG is traditionally also one of the main ingredients in Paintball fill because it is thick and flexible. However, as early as 2006, some Paintball manufacturers have been substituting PEG with cheaper alternatives.; PEGylation is the act of covalently coupling a PEG structure to another larger molecule, for example, a therapeutic protein (which is then referred to as PEGylated). PEGylated interferon alfa-2a or -2b is a commonly used injectable treatment for Hepatitis C infection.; Poly(ethylene glycol) (PEG), also known as poly(ethylene oxide) (PEO) or polyoxyethylene (POE), is the most commercially important type of polyether. PEG, PEO or POE refers to an oligomer or polymer of ethylene oxide. The three names are chemically synonymous, but historically PEG has tended to refer to oligomers and polymers with a molecular mass below 20,000 g/mol, PEO to polymers with a molecular mass above 20,000 g/mol, and POE to a polymer of any molecular mass. PEG and PEO are liquids or low-melting solids, depending on their molecular weights. PEGs are prepared by polymerization of ethylene oxide and are commercially available over a wide range of molecular weights from 300 g/mol to 10,000,000 g/mol. While PEG and PEO with different molecular weights find use in different applications and have different physical properties (e.g. viscosity) due to chain length effects, their chemical properties are nearly identical. Different forms of PEG are also available dependent on the initiator used for the polymerization process. The most common of which is a monofunctional methyl ether PEG (methoxypoly(ethylene glycol)), abbreviated mPEG. PEGs are also available with different geometries. Branched PEGs have 3 to 10 PEG chains emanating from a central core group. Star PEGs have 10 - 100 PEG chains emanating from a central core group. Comb PEGs have multiple PEG chains normally grafted to a polymer backbone.; Polyethylene glycol has a low toxicity and is used in a variety of products. It is the basis of a number of laxatives (e.g. macrogol-containing products such as Movicol and polyethylene glycol 3350, or SoftLax, MiraLax or GlycoLax). It is the basis of many skin creams, as cetomacrogol, and sexual lubricants, frequently combined with glycerin. Whole bowel irrigation (polyethylene glycol with added electrolytes) is used for bowel preparation before surgery or colonoscopy and drug overdoses. It is sold under the brand names GoLYTELY, NuLytely, GlycoLax, Fortrans, TriLyte, Colyte, Halflytely, MiraLAX, Softlax and MoviPrep. When attached to various protein medications, polyethylene glycol allows a slowed clearance of the carried protein from the blood. This makes for a longer acting medicinal effect and reduces toxicity, and it allows longer dosing intervals. Examples include PEG-interferon alpha, which is used to treat hepatitis C, and PEG-filgrastim (Neulasta), which is used to treat neutropenia. It has been shown that polyethylene glycol can improve healing of spinal injuries in dogs. One of the earlier findings that polyethylene glycol can aid in nerve repair came from the University of Texas (Krause and Bittner). Polyethylene glycol is commonly used to fuse B-cells with myeloma cells in monoclonal antibody production. PEG has recently been proved to give better results in constipation patients than tegaserod.; Since PEG is a flexible, water-soluble polymer, it can be used to create very high osmotic pressures (tens of atmospheres). It also is unlikely to have specific interactions with biological chemicals. These properties make PEG one of the most useful molecules for applying osmotic pressure in biochemistry experiments, particularly when using the osmotic stress technique.[citation needed]. Polyethylene glycol is found in many foods, some of which are turnip, mustard spinach, babassu palm, and watermelon.
CAS Number25322-68-3
Structure
Thumb
Synonyms
SynonymSource
8-Amino-7-oxononanoic acidKegg
7-Keto-8-aminopelargonic acidKegg
KAPAKegg
8-Amino-7-oxononanoateGenerator
7-Keto-8-aminopelargonateGenerator
1,2-EthanediolHMDB
a-hydro-W-Hydroxypoly(oxy-1,2-ethanediyl), 8ciHMDB
Ethane-1,2-diolHMDB
Ethylene alcoholHMDB
Ethylene glycolHMDB
Ethylene oxide polymerHMDB
GlycolHMDB
Glycol alcoholHMDB
L-GlycolHMDB
L-GlycolsHMDB
MiralaxHMDB
Monoethylene glycolHMDB
MXEHMDB
Poly(oxyethylene) glycolHMDB
Polyethylene glycol 6000HMDB
Polyethylene oxideHMDB
KAPA CPDMeSH
8-amino-7-OxononanoateGenerator
8-amino-7-Oxononanoic acidChEBI
a-Hydro-w-hydroxypoly(oxy-1,2-ethanediyl), 8CIdb_source
L-glycolbiospider
L-glycolsbiospider
Predicted Properties
PropertyValueSource
Water Solubility3.84 g/LALOGPS
logP-2ALOGPS
logP-1.3ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)4.45ChemAxon
pKa (Strongest Basic)8.08ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity48.74 m³·mol⁻¹ChemAxon
Polarizability20.5 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H17NO3
IUPAC name8-amino-7-oxononanoic acid
InChI IdentifierInChI=1S/C9H17NO3/c1-7(10)8(11)5-3-2-4-6-9(12)13/h7H,2-6,10H2,1H3,(H,12,13)
InChI KeyGUAHPAJOXVYFON-UHFFFAOYSA-N
Isomeric SMILESCC(N)C(=O)CCCCCC(O)=O
Average Molecular Weight187.2362
Monoisotopic Molecular Weight187.120843415
Classification
Description belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Amino fatty acid
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Alpha-aminoketone
  • Amino acid
  • Amino acid or derivatives
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organooxygen compound
  • Primary amine
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointMp 4-10°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-17c3ede7bedfb36ba628JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9200000000-e12b1dd57ad281415bd2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-c0d0f13370273a3df977JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fml-4900000000-a1203fcd7273968a2bc8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9200000000-32231d9309b57c1759b0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-61f02dfff7555912934fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-4900000000-35547c7e13e98cadcb2bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-9200000000-a46fc341642be806eacaJSpectraViewer
ChemSpider ID168
ChEMBL IDNot Available
KEGG Compound IDC01092
Pubchem Compound ID173
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB37790
CRC / DFC (Dictionary of Food Compounds) IDKVG76-Z:KVG76-Z
EAFUS ID3078
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPolyethylene_glycol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference