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Showing Compound Chitosan (FDB015634)

Record Information
Version1.0
Creation date2010-04-08 22:11:58 UTC
Update date2018-05-29 01:20:37 UTC
Primary IDFDB015634
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameChitosan
Descriptionobtained from Chitin BVM67-G by methods including alkaline hydrolysis and thermochemical-chemical treatment. It is used in edible coatings for fruit and vegetables and in biodegradable packaging films. Chitosan (pronounced /?ka?t?sæn/) is a linear polysaccharide composed of randomly distributed ?-(1-4)-linked D-glucosamine (deacetylated unit) and N-acetyl-D-glucosamine (acetylated unit). It has a number of commercial and possible biomedical uses.; Chitosan can also be used in water processing engineering as a part of a filtration process. Chitosan causes the fine sediment particles to bind together and is subsequently removed with the sediment during sand filtration. Chitosan also removes phosphorus, heavy minerals, and oils from the water. Chitosan is an important additive in the filtration process. Sand filtration apparently can remove up to 50% of the turbidity alone while the chitosan with sand filtration removes up to 99% turbidity. Chitosan has been used to precipitate caseins from bovine milk and cheese making; Chitosan has a rich history of being researched for applications in agriculture and horticulture dating back to the 1980s. By 1989 Bentech Labs patented chitosan salt solutions applied to crops for improved freeze protection or to crop seed for seed priming. Shortly thereafter Bentech's chitosan salt received the first ever biopesticide label from the EPA. Numerous other chitosan patents for plants soon followed. Chitosan applications to protect plants have been used in space as well. NASA first flew a chitosan experiment to protect adzuki beans grown aboard the space shuttle and Mir space station in 1997 (see photo left). NASA results revealed chitosan induces increased growth (biomass) and pathogen resistance due to elevated levels of beta 1-3 glucanase enzymes within plant cells. NASA confirmed chitosan elicits the same effect in plants on earth. Over 20 years of R&D by DuPont/ConAgra Ventures (DCV) and AgriHouse Inc have gone into developing non-toxic low molecular weight chitosan polymer solutions safe enough for broad spectrum agricultural and horticultural use. In 2008, AgriHouse Inc, Denver [Berthoud], Colorado, was granted EPA natural broad spectrum elicitor status for YEA!® Yield Enhancing Agent, a liquid solution containing an ultra low molecular active ingredient of 0.25% chitosan. YEA! is a next generation natural chitosan elicitor solution for agriculture and horticultural and was granted an amended label for foliar and irrigation applications by the EPA in June, 2009. A milliliter of YEA! contains over 14.4 X 10¹³ bio-active low molecular weight chitosan molecules and it is 600 times more effective than common chitosan). Given its low potential for toxicity and its abundance in the natural environment, chitosan does not harm people, pets, wildlife, or the environment when used according to label directions. Agricultural chitosan facts are located on USDA and EPA web sites.; Deacetylated CHITIN, a linear polysaccharide of deacetylated beta-1,4-D-glucosamine. It is used in HYDROGEL and to treat WOUNDS.; Chitosan can also be used in water processing engineering as a part of a filtration process. Chitosan causes the fine sediment particles to bind together and is subsequently removed with the sediment during sand filtration. Chitosan also removes phosphorous, heavy minerals, and oils from the water. Chitosan is an important additive in the filtration process. Sand filtration apparently can remove up to 50% of the turbidity alone while the Chitosan with sand filtration removes up to 99% turbidity.; Chitosan is a linear polysaccharide composed of randomly distributed beta(1->4)-linked D-glucosamine (deacetylated unit) and N-acetyl-D-glucosamine (acetylated unit). It has a number of commercial amd possible biomedical uses.; In agriculture, chitosan is used primarily as a natural seed treatment and plant growth enhancer, and as a substance that boosts the ability of plants to defend against fungal infections. The natural biocontrol active ingredient, chitin/chitosan, are found in the shells of crustaceans, such as lobsters, crabs, and shrimp, and many other organisms including insects and fungi. It is one of the most abundant bio-gradable materials in the world. Degraded molecules of chitin/chitosan exist in soil and water. Chitosan applications for plants and crops are regulated by the EPA and the USDA National Organic Program regulates its use on organic certified farms and crops. It is approved for use outdoors and indoors on plants and crops grown commercially and by consumers. The natural biocontrol ability of chitosan should not be confused with the effects of fertilizers or pesticides upon plants or the environment. It represents a new tier of cost effective biological control of crops.
CAS Number9012-76-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility697 g/LALOGPS
logP-2ALOGPS
logP-2.3ChemAxon
logS0.59ALOGPS
pKa (Strongest Acidic)12.93ChemAxon
pKa (Strongest Basic)8.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area95.94 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.97 m³·mol⁻¹ChemAxon
Polarizability17.97 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H15NO4
IUPAC name5-amino-2-(hydroxymethyl)-6-methyloxane-3,4-diol
InChI IdentifierInChI=1S/C7H15NO4/c1-3-5(8)7(11)6(10)4(2-9)12-3/h3-7,9-11H,2,8H2,1H3
InChI KeyXJSPDRFMLGJORM-UHFFFAOYSA-N
Isomeric SMILESCC1OC(CO)C(O)C(O)C1N
Average Molecular Weight177.1983
Monoisotopic Molecular Weight177.100107973
Classification
Description Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Amino saccharide
  • Oxane
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Organopnictogen compound
  • Primary amine
  • Primary alcohol
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Amine
  • Alcohol
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-c7345b9e3c4d5bdc4eb02016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08i3-5900000000-a8cd904388017de1dca82016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5l-9100000000-2569099d3eb3998d9b172016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-8900000000-7dc1c20e2381a46481f42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0adi-9600000000-0bf083cbb080f8ac1c062016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9000000000-1dca6a354b03e503d2e22016-08-03View Spectrum
NMRNot Available
ChemSpider ID64870
ChEMBL IDNot Available
KEGG Compound IDC00734
Pubchem Compound ID71853
Pubchem Substance IDNot Available
ChEBI ID16261
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03404
CRC / DFC (Dictionary of Food Compounds) IDKFJ67-E:KFJ67-E
EAFUS IDNot Available
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 IDChitosan
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference