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68264

Sigma-Aldrich

α-Hydroxyisobutyronitrile β-D-glucopyranoside

≥97% (HPLC)

Synonyme(s) :

α-Hydroxyisobutyronitrile β-D-glucose, 2-(β-D-Glucopyranosyloxy)-2-methylpropionitrile, Linamarin

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About This Item

Formule empirique (notation de Hill):
C10H17NO6
Numéro CAS:
554-35-8
Poids moléculaire :
247.25
Numéro MDL:
MFCD00036209
Code UNSPSC :
12352201
ID de substance PubChem :
329760502
Nomenclature NACRES :
NA.25

Source biologique

synthetic

Niveau de qualité

100

Pureté

≥97% (HPLC)

Forme

solid

Activité optique

[α]/D -26.5±2.0°, c = 1 in H2O

Technique(s)

HPLC: suitable

Couleur

white to off-white

Température de stockage

2-8°C

Chaîne SMILES 

CC(C)(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C#N

InChI

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

Clé InChI

QLTCHMYAEJEXBT-ZEBDFXRSSA-N

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Application

Linamarin, a cyanogenic glucose substrate, is used together with β-glucosidase, linamarase, to produce cyanide in vivo as a potential anticancer strategy.

Actions biochimiques/physiologiques

Linamarin is a cyanogenic glucoside found in the leaves and roots of plants such as cassava, lima beans, and flax. 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

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Autres remarques

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302 + H332,H315,H319,H335

Classification des risques

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

Christopher Avwoghokoghene Idibie et al.
Bioprocess and biosystems engineering, 30(4), 261-269 (2007-06-15)
Cassava (Manihot esculenta Crantz) is a known source of linamarin, but difficulties associated with its isolation have prevented it from being exploited as a major source. A batch adsorption process using activated carbon proved successful in its isolation, with ultrafiltration
Christine Männel-Croisé et al.
Analytical chemistry, 81(22), 9493-9498 (2009-10-22)
Corrin-based chemosensors allow the rapid and selective colorimetric detection of endogenous biological cyanide. The color change from orange to violet can be easily observed with the "naked eye" (Deltalambda(max) = 51 nm). The methodology works directly in the biological matrix
Eduardo Rivadeneyra-Domínguez et al.
Toxins, 12(11) (2020-11-14)
Cassava (Manihot esculenta Crantz) is a plant that contains neurotoxins such as linamarin and lotaustraline. Its long-term consumption is associated with neuronal damage and contributes to the development of motor impairment in humans and rats. We investigated the effects of
Bala Nambisan
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 49(3), 690-693 (2010-11-16)
Toxicity of cassava arises due to the presence of the cyanoglucosides linamarin and lotaustralin which are hydrolysed by endogenous enzyme linamarase to acetonecyanohydrin (ACN) and cyanide (CN) which are toxic. Major research efforts to eliminate/reduce cyanoglucosides have focused on (i)
Stefan Pentzold et al.
Scientific reports, 6, 22407-22407 (2016-03-05)
Insects often release noxious substances for their defence. Larvae of Zygaena filipendulae (Lepidoptera) secrete viscous and cyanogenic glucoside-containing droplets, whose effectiveness was associated with their physical and chemical properties. The droplets glued mandibles and legs of potential predators together and
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