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Merck

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:
Peso molecular:
311.29
EC Number:
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.25

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

signalword

Warning

hcodes

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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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
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
D B Tattersall et al.
Science (New York, N.Y.), 293(5536), 1826-1828 (2001-07-28)
The entire pathway for synthesis of the tyrosine-derived cyanogenic glucoside dhurrin has been transferred from Sorghum bicolor to Arabidopsis thaliana. Here, we document that genetically engineered plants are able to synthesize and store large amounts of new natural products. The
Plant science. Dynamic metabolons.
Birger Lindberg Møller
Science (New York, N.Y.), 330(6009), 1328-1329 (2010-12-04)
Kirsten A Nielsen et al.
Planta, 223(5), 1010-1023 (2005-11-25)
Barley (Hordeum vulgare L.) produces a leucine-derived cyanogenic beta-D-glucoside, epiheterodendrin that accumulates specifically in leaf epidermis. Barley leaves are not cyanogenic, i.e. they do not possess the ability to release hydrogen cyanide, because they lack a cyanide releasing beta-D-glucosidase. Cyanogenesis

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