Linamarine

Structural formula
General
Surname	Linamarine
other names	2-methyl-2 - [(2 S , 3 R , 4 S , 5 S , 6 R ) -3,4,5-trihydroxy-6- (hydroxymethyl) oxan-2-yl] oxypropanenitrile; (2-cyano-2-propyl) -β- D -glucopyranoside; O- β- D -glucopyranosyl-2-hydroxy-2-methylpropionitrile;
Molecular formula	C 10 H 17 NO 6
Brief description	colorless needles
External identifiers / databases
EC number	637-249-5
ECHA InfoCard	100.164.971
PubChem	11128
Wikidata	Q425157
properties
Molar mass	247.25 g mol −1
Physical state	firmly
Melting point	143-144 ° C
solubility	good in water and ethanol ; insoluble in diethyl ether ;
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-315-319-332-335
	P: 261-305 + 351 + 338
Toxicological data	500 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Linamarine is a cyanogenic glycoside isolated from the leaves and roots of plants such as cassava , lima bean or flax . The aglycon is the cyanohydrin of acetone ; the sugar building block is glucose . A glycoside that is chemically closely related to linamarine is Lotaustralin , which has a slightly different aglycon.

When it comes into contact with enzymes and the intestinal flora in the human digestive system, linamarine is broken down into the toxic hydrogen cyanide.

Consumption of low-linamarine cassava products is widespread in the lowland tropics, so poorly processed high-linamarine cassava roots have been the cause of food-borne poisoning there. The upper motor neurons were particularly affected and this condition became known as Konzo . The disease was first described by Trolli and later by a research group under Hans Rosling.

Food-related consumption of linamarin has been viewed as a risk factor for developing glucose intolerance and diabetes . However, this could not be reliably confirmed in animal experiments. Today it is assumed that linamarin can promote existing diseases, but is not the cause of a disease.

The formation of prussic acid from linamarine is an enzymatic process and is caused by linamarase , which is located in the cell walls of the plant. Due to the volatility of hydrogen cyanide, the poison is removed during processing into food by bleaching in sunlight, cooking or fermentation. In this way, products like be Garri , Fufu and Agbelima made from cassava.

In a study from 2003, the linamarin formation in the plant was reduced with the help of genetic engineering.

Individual evidence

↑ ^a ^b ^c Shmuel Yannai: Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. CRC Press, 2003, ISBN 978-1-58488-416-3 , p. 695.
↑ ^a ^b Entry on Linamarin. In: Römpp Online . Georg Thieme Verlag, accessed on June 1, 2014.
↑ ^a ^b Data sheet α-Hydroxyisobutyronitrile β-D-glucopyranoside from Sigma-Aldrich , accessed on April 7, 2011 ( PDF ).
^ Toxicology and Applied Pharmacology . Vol. 42, Pg. 539, 1977.
↑ Entry on Linamarin in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ JP Banea-Mayambu, T. Tylleskar, N. Gitebo, N. Matadi, M. Gebre-Medhin, H. Rosling: Geographical and seasonal association between linamarin and cyanide exposure from cassava and the upper motor neurone disease konzo in former Zaire , Trop Med Int Health 1997 , 2 , 1143-1151; PMID 9438470 .
↑ B. Soto-Blanco, PC Marioka, SL Gorniak: Effects of long-term low-dose cyanide administration to rats , Ecotoxicol Environ Saf 2002 , 53 , 37-41; PMID 12481854 .
↑ A. Yessoufou, JM Ategbo, A. Girard, J. Prost, KL Dramane, K. Moutairou, A. Hichami, NA Khan: Cassava-enriched diet is not diabetogenic rather it aggravates diabetes in rats . In: Fundam Clin Pharmacol 2002 , 20 , 579-586; PMID 17109651 .
↑ G. Padmaja: Cyanide detoxification in cassava for food and feed uses . Crit Rev Food Sci Nutr 1995 , 35 , 299-339; PMID 7576161 .
↑ D. Siritunga, R. Sayre: In Generation of cyanogen-free transgenic cassava , Planta 2003 , 217 , 367-373; PMID 14520563 .

[dofc-1] Shmuel Yannai: Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. CRC Press, 2003, ISBN 978-1-58488-416-3 , p. 695.

[roempp-2] Entry on Linamarin. In: Römpp Online . Georg Thieme Verlag, accessed on June 1, 2014.

[Sigma-3] Data sheet α-Hydroxyisobutyronitrile β-D-glucopyranoside from Sigma-Aldrich , accessed on April 7, 2011 ( PDF ).

[4] Toxicology and Applied Pharmacology . Vol. 42, Pg. 539, 1977.

[5] Entry on Linamarin in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[Banea-6] JP Banea-Mayambu, T. Tylleskar, N. Gitebo, N. Matadi, M. Gebre-Medhin, H. Rosling: Geographical and seasonal association between linamarin and cyanide exposure from cassava and the upper motor neurone disease konzo in former Zaire , Trop Med Int Health 1997 , 2 , 1143-1151; PMID 9438470 .

[Soto-7] B. Soto-Blanco, PC Marioka, SL Gorniak: Effects of long-term low-dose cyanide administration to rats , Ecotoxicol Environ Saf 2002 , 53 , 37-41; PMID 12481854 .

[Yessoufou-8] A. Yessoufou, JM Ategbo, A. Girard, J. Prost, KL Dramane, K. Moutairou, A. Hichami, NA Khan: Cassava-enriched diet is not diabetogenic rather it aggravates diabetes in rats . In: Fundam Clin Pharmacol 2002 , 20 , 579-586; PMID 17109651 .

[Padmaja-9] G. Padmaja: Cyanide detoxification in cassava for food and feed uses . Crit Rev Food Sci Nutr 1995 , 35 , 299-339; PMID 7576161 .

[Siritunga1-10] D. Siritunga, R. Sayre: In Generation of cyanogen-free transgenic cassava , Planta 2003 , 217 , 367-373; PMID 14520563 .