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07743

Sigma-Aldrich

Dhurrin

≥95% (HPLC)

Sinónimos:

(S)-(β-D-Glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile, (S)-4-Hydroxymandelonitrile β-D-glucoside

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About This Item

Fórmula empírica (notación de Hill):
C14H17NO7
Número de CAS:
499-20-7
Peso molecular:
311.29
EC Number:
207-878-6
MDL number:
MFCD18632527
UNSPSC Code:
12352201
PubChem Substance ID:
329748512
NACRES:
NA.25

Quality Level

100

assay

≥95% (HPLC)

form

powder or crystals

color

white to light brown

storage temp.

room temp

SMILES string

OC[C@H]1O[C@@H](O[C@H](C#N)c2ccc(O)cc2)[C@H](O)[C@@H](O)[C@@H]1O

InChI

1S/C14H17NO7/c15-5-9(7-1-3-8(17)4-2-7)21-14-13(20)12(19)11(18)10(6-16)22-14/h1-4,9-14,16-20H,6H2/t9-,10-,11-,12+,13-,14-/m1/s1

InChI key

NVLTYOJHPBMILU-YOVYLDAJSA-N

General description

Dhurrin is a cyanogenic glucoside found expressed in the leaves of Sorghum plants. Studies have shown that as the plant ages, dhurrin expression depends are nitrogen availability. Dhurrin production shifts from the leaves to the stems during development.

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

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

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Johan Memelink
Trends in plant science, 10(7), 305-307 (2005-06-14)
Metabolic engineering holds great promise as a technique for improving crop plants. However, introducing new metabolic steps can disturb normal metabolism and gene expression, affecting phenotype and quality in undesired ways. Recently, Charlotte Kristensen et al. reported that introducing the
Gina Rosalinda De Nicola et al.
Journal of agricultural and food chemistry, 59(15), 8065-8069 (2011-06-29)
Cyanogenic plants have some potential as biocidal green manure crops in limiting several soilborne pests and pathogens. Sorghum (Sorghum bicolor (L.) Moench) and Sudangrass (Sorghum bicolor subsp. sudanense (P.) Stapf), in fact, contain the cyanogenic glucoside p-hydroxy-(S)-mandelonitrile-β-D-glucoside (dhurrin) as a
Cecilia K Blomstedt et al.
Plant biotechnology journal, 10(1), 54-66 (2011-09-02)
Cyanogenic glucosides are present in several crop plants and can pose a significant problem for human and animal consumption, because of their ability to release toxic hydrogen cyanide. Sorghum bicolor L. contains the cyanogenic glucoside dhurrin. A qualitative biochemical screen
Henrik Johansen et al.
Chemosphere, 67(2), 259-266 (2006-11-28)
Cyanogenic glycosides are common plant toxins. Toxic hydrogen cyanide originating from cyanogenic glycosides may affect soil processes and water quality. In this study, hydrolysis, degradation and sorption of dhurrin (4-hydroxymandelonitrile-beta-d-glucoside) produced by sorghum has been studied in order to assess
Charlotte Kristensen et al.
Proceedings of the National Academy of Sciences of the United States of America, 102(5), 1779-1784 (2005-01-25)
Focused and nontargeted approaches were used to assess the impact associated with introduction of new high-flux pathways in Arabidopsis thaliana by genetic engineering. Transgenic A. thaliana plants expressing the entire biosynthetic pathway for the tyrosine-derived cyanogenic glucoside dhurrin as accomplished
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