{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 442096935 | ImageFile1 = Linamarin.svg | ImageSize1 = | ImageFile2 = Linamarin3d.png | ImageSize2 = | ImageFile3 = Linamarin 3D sticks.png | IUPACName = 2-(β-<small>D</small>-Glucopyranosyloxy)-2-methylpropanenitrile | SystematicName = 2-Methyl-2-<nowiki/>{[(2''S'',3''R'',4''S'',5''S'',6''R'')-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanenitrile | OtherNames = Phaseolunatin |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|??}} | CASNo = 554-35-8 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = H3V9RP3WLO | PubChem = 11128 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 3039425 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 10657 | SMILES = CC(C)(C#N)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O | InChI = 1/C10H17NO6/c1-10(2,4-11)17-9-8(15)7(14)6(13)5(3-12)16-9/h5-9,12-15H,3H2,1-2H3/t5-,6-,7+,8-,9+/m1/s1 | InChIKey = QLTCHMYAEJEXBT-ZEBDFXRSBH | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C10H17NO6/c1-10(2,4-11)17-9-8(15)7(14)6(13)5(3-12)16-9/h5-9,12-15H,3H2,1-2H3/t5-,6-,7+,8-,9+/m1/s1 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = QLTCHMYAEJEXBT-ZEBDFXRSSA-N | RTECS = | MeSHName = | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 16441 | KEGG_Ref = {{keggcite|changed|kegg}} | KEGG = C01594}} |Section2={{Chembox Properties | MolarMass = 247.248 g/mol | Appearance = colorless needles <ref name=dofc>Shmuel Yannai: ''Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients.'' CRC Press, 2003, {{ISBN|978-1-58488-416-3}}, P. 695</ref> | C=10 | H=17 | N=1 | O=6 | Density = 1.41 g·cm<sup>−3</sup> | MeltingPtC = 143 to 144 | MeltingPt_ref = <ref name=dofc/> | Solubility = good <ref name=dofc/> | BoilingPt = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }} '''Linamarin''' is a cyanogenic glucoside found in the leaves and roots of plants such as cassava, lima beans, and flax. It is a glucoside of acetone cyanohydrin. Upon exposure to enzymes and gut flora in the human intestine, linamarin and its methylated relative lotaustralin can decompose to the toxic chemical hydrogen cyanide; hence food uses of plants that contain significant quantities of linamarin require extensive preparation and detoxification. Ingested and absorbed linamarin is rapidly excreted in the urine and the glucoside itself does not appear to be acutely toxic. Consumption of cassava products with low levels of linamarin is widespread in the low-land tropics. Ingestion of food prepared from insufficiently processed cassava roots with high linamarin levels has been associated with dietary toxicity, particularly with the upper motor neuron disease known as konzo to the African populations in which it was first described by Trolli and later through the research network initiated by Hans Rosling. However, the toxicity is believed to be induced by ingestion of acetone cyanohydrin, the breakdown product of linamarin.<ref name="Banea">{{cite journal | last1 = Banea-Mayambu | first1 = JP | last2 = Tylleskar | first2 = T | last3 = Gitebo | first3 = N | last4 = Matadi | first4 = N | last5 = Gebre-Medhin | first5 = M | last6 = Rosling | first6 = H | year = 1997 | title = Geographical and seasonal association between linamarin and cyanide exposure from cassava and the upper motor neurone disease konzo in former Zaire | url = | journal = Trop Med Int Health | volume = 2 | issue = 12| pages = 1143–51 | pmid = 9438470 }}</ref> Dietary exposure to linamarin has also been reported as a risk factor in developing glucose intolerance and diabetes, although studies in experimental animals have been inconsistent in reproducing this effect<ref name="Soto">{{cite journal | last1 = Soto-Blanco | first1 = B | last2 = Marioka | first2 = PC | last3 = Gorniak | first3 = SL | year = 2002 | title = Effects of long-term low-dose cyanide administration to rats | url = | journal = Ecotoxicol Environ Saf | volume = 53 | issue = 1| pages = 37–41 | pmid = 12481854 }}</ref><ref name="Soto-Blanco B 2001">Soto-Blanco B, Sousa AB, Manzano H, Guerra JL, Gorniak SL. 2001. Does prolonged cyanide exposure have a diabetogenic effect?. Vet Hum Toxicol. 43(2):106-8.</ref> and may indicate that the primary effect is in aggravating existing conditions rather than inducing diabetes on its own.<ref name="Soto-Blanco B 2001"/><ref name="Yessoufou">{{cite journal | last1 = Yessoufou | first1 = A | last2 = Ategbo | first2 = JM | last3 = Girard | first3 = A | last4 = Prost | first4 = J | last5 = Dramane | first5 = KL | last6 = Moutairou | first6 = K | last7 = Hichami | first7 = A | last8 = Khan | first8 = NA | year = 2002 | title = Cassava-enriched diet is not diabetogenic rather it aggravates diabetes in rats | url = | journal = Fundam Clin Pharmacol | volume = 20 | issue = 6| pages = 579–86 | pmid = 17109651 | doi = 10.1111/j.1472-8206.2006.00443.x }}</ref>
The generation of cyanide from linamarin is usually enzymatic and occurs when linamarin is exposed to linamarase, an enzyme normally expressed in the cell walls of cassava plants. Because the resulting cyanide derivatives are volatile, processing methods that induce such exposure are common traditional means of cassava preparation; foodstuffs are usually made from cassava after extended blanching, boiling, or fermentation.<ref name="Padmaja">{{cite journal | last1 = Padmaja | first1 = G | year = 1995 | title = Cyanide detoxification in cassava for food and feed uses | url = | journal = Crit Rev Food Sci Nutr | volume = 35 | issue = 4| pages = 299–339 | pmid = 7576161 | doi = 10.1080/10408399509527703 }}</ref> Food products made from cassava plants include garri (toasted cassava tubers), porridge-like fufu, the dough agbelima, and cassava flour.
Research efforts have developed a transgenic cassava plant that stably downregulates linamarin production via RNA interference.<ref name="Siritunga1">{{cite journal | doi = 10.1007/s00425-003-1005-8 | title = Generation of cyanogen-free transgenic cassava | date = 2003 | last1 = Siritunga | first1 = Dimuth | last2 = Sayre | first2 = Richard T. | journal = Planta | volume = 217 | issue = 3 | pages = 367–373 | pmid = 14520563 | bibcode = 2003Plant.217..367S }}</ref>
== References == <references />
{{Glycosides}}
Category:Plant toxins Category:Cyanogenic glycosides