| Identification | Back Directory | [Name]
LINAMARIN | [CAS]
554-35-8 | [Synonyms]
LINAMARIN
Linamarine
PHASEOLUNATIN
Phaseolunatine
Linamarin min. 99%
Phaseolunatin =Linamarin
α-Hydroxyisobutyronitrile β-D-Glucose
2-(beta-d-glucopyranosyloxy)isobutyronitrile
alpha-hydroxyisobutyronitrile-beta-d-glucose
α-Hydroxyisobutyronitrile β-D-glucopyranoside
2-(β-D-Glucopyranosyloxy)-2-methylpropionitrile
2-(?D-Glucopyranosyloxy)-2-methyl-propanenitrile
2-(b-D-Glucopyranosyloxy)-2-methyl-propanenitrile
2-(beta-d-glucopyranosyloxy)-2-methyl-propanenitril
ALPHA-HYDROXYISOBUTYRONITRILE-BETA-D-GLUCOPYRANOSIDE
2-(BETA-D-GLUCOPYRANOSYLOXY)-2-METHYL-PROPANENITRILE
2-(alpha-D-Glucopyranosyloxy)-2-methylpropanenitrile
2-(beta-D-Glucopyranosyloxy)-2-methyl-propanenitrile, Phaseolunatin
2-(D-GLUCOPYRANOSYLOXY)-2-METHYL-PROPANENITRILE,PHASEOLUNATIN=LINAMARIN
2-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropanenitrile
2-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-propanenitrile
2-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methylol-tetrahydropyran-2-yl]oxy-propionitrile
α-Hydroxyisobutyronitrile β-D-glucose, 2-(β-D-Glucopyranosyloxy)-2-methylpropionitrile, Linamarin | [Molecular Formula]
C10H17NO6 | [MDL Number]
MFCD00036209 | [MOL File]
554-35-8.mol | [Molecular Weight]
247.25 |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Solid | [Melting point ]
142-143°C | [alpha ]
D18 -29° | [Boiling point ]
390.28°C (rough estimate) | [density ]
1.2868 (rough estimate) | [refractive index ]
1.4610 (estimate) | [storage temp. ]
2-8°C | [solubility ]
Soluble in DMSO, Methanol, and Ethanol | [form ]
solid | [pka]
12.73±0.70(Predicted) | [color ]
White or off-white | [optical activity]
[α]/D -26.5±2.0°, c = 1 in H2O | [Stability:]
Acid Sensitive |
| Hazard Information | Back Directory | [Chemical Properties]
White Crystalline Solid | [Uses]
Can be found in the seed skins and embryos of flax | [Description]
Linamarin is a glucoside of acetone cyanohydrin found in the leaves and roots of cassava, lima beans, and flax.1 It is thought to function in the transport of nitrogen from plant leaves to roots in young plants but also serves as a plant defense mechanism. Linamarin is converted to toxic hydrocyanic acid or prussic acid when it comes into contact with linamarase, an enzyme that is released when the cells of cassava roots are ruptured.2 | [Definition]
ChEBI: Linamarin is a beta-D-glucoside. It is functionally related to a 2-hydroxy-2-methylpropanenitrile. | [storage]
Store at -20°C | [References]
1) Jensen?et al.?(2011),?Convergent evolution in biosynthesis if cyanogenic defense compounds in plants; Nat. Commun.,?2?273
2) Rivadeneyra?et al. (2013),?Neurotoxic effect of linamarin in rats associated with cassava (Manihot esculenta Crantz) consumption; Food Chem. Toxicol.,?59?230
3) Kimani?et al. (2014),?Memory deficits associated with sublethal cyanide poisoning relative to cyanate toxicity in rodents; Metab. Brain Dis.,?29?105 |
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