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Merck

68264

α-Hydroxyisobutyronitrile β-D-glucopyranoside

≥97% (HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C10H17NO6
Número CAS:
554-35-8
Peso molecular:
247.25
NACRES:
NA.25
PubChem Substance ID:
329760502
UNSPSC Code:
12352201
MDL number:
MFCD00036209

Nombre del producto

α-Hydroxyisobutyronitrile β-D-glucopyranoside, ≥97% (HPLC)

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

SMILES string

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

InChI key

QLTCHMYAEJEXBT-ZEBDFXRSSA-N

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

Quality Level

100

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Categorías relacionadas

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

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
BCCN4025
BCCL5275
BCCK1273
BCCH3817
BCCF2958

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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
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
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
Hung Su et al.
Journal of food and drug analysis, 27(2), 415-427 (2019-04-17)
The unintentional ingestion of toxic compounds in herbs is not uncommon in many parts of the world. To provide timely and life-saving care in the emergency department, it is essential to develop a point-of-care analytical method that can rapidly identify
Lotte Kolind-Hansen et al.
Journal of the science of food and agriculture, 90(2), 252-256 (2010-04-01)
A number of retail shops in Copenhagen sell fresh cassava roots. Cassava roots contain the toxic cyanogenic glucoside linamarin. A survey was made of the shop characteristics, origin of the roots, buyers, shop owner's knowledge of toxicity levels, and actual
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