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07743

Sigma-Aldrich

Dhurrin

≥95% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C14H17NO7
CAS Number:
499-20-7
Molecular Weight:
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
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

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK7326
BCCG7415
BCCG3491
BCCC2664
BCBW0116

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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
Plant science. Dynamic metabolons.
Birger Lindberg Møller
Science (New York, N.Y.), 330(6009), 1328-1329 (2010-12-04)
Cyanogenic glycosides and menisdaurin from Guazuma ulmifolia, Ostrya virgininana, Tiquilia plicata and Tiquilia canescens.
David S Seigler
Phytochemistry, 66(13), 1567-1580 (2005-07-09)
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
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