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68264

Sigma-Aldrich

α-Hydroxyisobutyronitrile β-D-glucopyranoside

≥97% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C10H17NO6
CAS Number:
554-35-8
Molecular Weight:
247.25
MDL number:
MFCD00036209
UNSPSC Code:
12352201
PubChem Substance ID:
329760502
NACRES:
NA.25

biological source

synthetic

Quality Level

100

Assay

≥97% (HPLC)

form

solid

optical activity

[α]/D -26.5±2.0°, c = 1 in H2O

technique(s)

HPLC: suitable

color

white to off-white

storage temp.

2-8°C

SMILES string

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

InChI key

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.

Biochem/physiol Actions

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

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
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
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
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
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