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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

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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Mika Zagrobelny et al.
Insect biochemistry and molecular biology, 37(11), 1189-1197 (2007-10-06)
Zygaena larvae sequester the cyanogenic glucosides (CNglcs) linamarin and lotaustralin from their food plants (Fabaceae) and also de novo biosynthesize these compounds. In Zygaenidae, CNglcs serve as defence compounds during the entire life cycle, and their content and ratio are
Karin Forslund et al.
Plant physiology, 135(1), 71-84 (2004-05-04)
Lotus japonicus was shown to contain the two nitrile glucosides rhodiocyanoside A and rhodiocyanoside D as well as the cyanogenic glucosides linamarin and lotaustralin. The content of cyanogenic and nitrile glucosides in L. japonicus depends on plant developmental stage and
Vega García-Escudero et al.
Autophagy, 4(7), 923-925 (2008-08-22)
The understanding of the mechanisms of cell-death execution and the role that they play in different diseases opens new therapeutic strategies. Currently, increasing evidence indicates that autophagy is a frequent cell-death mechanism, so the question arises: Could autophagy stimulation be
Kirsten Jørgensen et al.
Plant physiology, 155(1), 282-292 (2010-11-04)
Cassava (Manihot esculenta) is a eudicotyledonous plant that produces the valine- and isoleucine-derived cyanogenic glucosides linamarin and lotaustralin with the corresponding oximes and cyanohydrins as key intermediates. CYP79 enzymes catalyzing amino acid-to-oxime conversion in cyanogenic glucoside biosynthesis are known from
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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