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chitin

File:Chitin.svg · Wikimedia Commons · See Wikimedia Commons

EntityQ161219· pop 72· linked from 834 articles

thumb|250px|right|Structure of the chitin molecule, showing two of the N-Acetylglucosamine|N-acetylglucosamine units that repeat to form long chains in β-(1→4)-linkage. thumb|250px|right|Haworth projection of the chitin molecule. thumb|A close-up of the wing of a leafhopper; the wing is composed of chitin. thumb|right|A cicada emerges from its nymphal exoskeleton; the shed exoskeleton is mostly modified chitin ([[sclerotin) but the wings and much of the adult body are still unsclerotized chitin at this stage]]

OverviewAI-generated

Chitin is a chemical compound with the IUPAC name N-[(2R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide. Its molecular structure is represented by the SMILES notation CC(=O)NC1[C@@H](OC(C(C1O)O)CO)O. The substance has a mass of 203.1925 and a weight of 221.21.

Chemical properties of chitin include an xlogp value of -1.7 and a topological polar surface area of 119. The molecule contains five hydrogen bond donors and six hydrogen bond acceptors, with a charge of 0. It is identified in the PubChem database by the CID 6857375 and the InChIKey OVRNDRQMDRJTHS-WTZNIHQSSA-N.

Chitin is the subject of 53,360 entries in the PubMed database. It is also referenced by 834 other encyclopedia articles.

Synthesized by Vinony from 15 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Chemical data

Formula
C8H15NO6
Molecular weight
221.21 g/mol
IUPAC name
N-[(2R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
SMILES
CC(=O)NC1[C@@H](OC(C(C1O)O)CO)O
InChIKey
OVRNDRQMDRJTHS-WTZNIHQSSA-N
XLogP
-1.7
Polar surface area
119 Ų
H-bond donors
5
H-bond acceptors
6
Formal charge
0

via PubChem

Research

53,360 papers

via PubMed

~8 min read

Encyclopedic overview

12 sections
Contents
  • Etymology
  • Chemistry, physical properties and biological function
  • Humans and other mammals
  • Plants
  • Fossil record
  • Uses
  • Agriculture
  • Industrial
  • Research
  • See also
  • References
  • External links

thumb|250px|right|Structure of the chitin molecule, showing two of the N-Acetylglucosamine|N-acetylglucosamine units that repeat to form long chains in β-(1→4)-linkage. thumb|250px|right|Haworth projection of the chitin molecule. thumb|A close-up of the wing of a leafhopper; the wing is composed of chitin. thumb|right|A cicada emerges from its nymphal exoskeleton; the shed exoskeleton is mostly modified chitin ([[sclerotin) but the wings and much of the adult body are still unsclerotized chitin at this stage]]

Chitin (C8H13O5N)n ( ) is a long-chain polymer of N-acetylglucosamine, an amide derivative of glucose. Chitin is the second most abundant polysaccharide in nature (behind only cellulose); an estimated 1 billion tons of chitin are produced each year in the biosphere. It is a primary component of cell walls in fungi (especially filamentous and mushroom-forming fungi), the exoskeletons of arthropods such as crustaceans and insects, the radulae, cephalopod beaks and gladii of molluscs and in some nematodes and diatoms. It is also synthesised by at least some fish and lissamphibians. Commercially, chitin is extracted from the shells of crabs, shrimps, shellfish and lobsters, which are major by-products of the seafood industry. The structure of chitin is comparable to cellulose, forming crystalline nanofibrils or whiskers. It is functionally comparable to the protein keratin. Chitin has proved useful for several medicinal, industrial and biotechnological purposes.

Excerpted from Wikipedia’s “chitin” article, available under the CC BY-SA 4.0 licence.

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