File:Chitin.svg · Wikimedia Commons · See Wikimedia Commons
chitin
Sign in to savethumb|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- Chitin in Arthropods: Biosynthesis, Modification, and Metabolism.ReviewAdvances in experimental medicine and biology · 2019Liu X, Zhang J, Zhu KYDOI: 10.1007/978-981-13-7318-3_9
- Chitin Synthesis and Degradation in Crustaceans: A Genomic View and Application.ReviewMarine drugs · 2021Zhang X, Yuan J, Li F et al.DOI: 10.3390/md19030153
- Deciphering the Chitin Code in Plant Symbiosis, Defense, and Microbial Networks.ReviewAnnual review of microbiology · 2021Khokhani D, Carrera Carriel C, Vayla S et al.DOI: 10.1146/annurev-micro-051921-114809
- Chitin and its derivatives: Functional biopolymers for developing bioproducts for sustainable agriculture-A reality?ReviewCarbohydrate polymers · 2023Giraldo JD, Garrido-Miranda KA, Schoebitz MDOI: 10.1016/j.carbpol.2022.120196
- Chitin deacetylases: properties and applications.ReviewMarine drugs · 2010Zhao Y, Park RD, Muzzarelli RADOI: 10.3390/md8010024
- Chitin isolation from crustaceans and mushrooms: The need for quantitative assessment.ReviewCarbohydrate polymers · 2025Zannat A, Shamshina JLDOI: 10.1016/j.carbpol.2024.122882
- Chitin Organizing and Modifying Enzymes and Proteins Involved In Remodeling of the Insect Cuticle.ReviewAdvances in experimental medicine and biology · 2019Muthukrishnan S, Merzendorfer H, Arakane Y et al.DOI: 10.1007/978-981-13-7318-3_5
- Patentology of chitinous biomaterials. Part I: Chitin.ReviewCarbohydrate polymers · 2022Kertmen A, Ehrlich HDOI: 10.1016/j.carbpol.2022.119102
via PubMed
~8 min read
Encyclopedic overview
12 sectionsContents
- 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.
Gallery (16)
Available in 71 languages
- Español
- Français
- Deutsch
- 中文
- 日本語
- Русский
- Português
- Italiano
- العربية
- हिन्दी
- Armenian
- Asturian
- Azerbaijani
- Bahasa Indonesia
- Bangla
- Bashkir
- Basque
- be_x_old
Show 52 more
- Belarusian
- Bosnian
- Bulgarian
- Catalan
- Croatian
- Czech
- Danish
- Esperanto
- Estonian
- Finnish
- Galician
- Georgian
- Greek
- Haitian Creole
- Hebrew
- Hungarian
- hyw
- Icelandic
- Ido
- Irish
- Javanese
- Kannada
- Kazakh
- Latin
- Latvian
- Lithuanian
- Malay
- Nederlands
- Norwegian
- Norwegian Nynorsk
- Polski
- Romanian
- Serbian
- Serbian (Latin)
- simple
- Slovak
- Slovenian
- Sundanese
- Svenska
- Swahili
- Tamil
- Tiếng Việt
- Türkçe
- Ukrainian
- Urdu
- Uzbek
- Welsh
- Wu Chinese
- zh_yue
- فارسی
- ไทย
- 한국어
via Wikidata sitelinks · CC0