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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

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

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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Toni M Kutchan
Trends in biotechnology, 23(8), 381-383 (2005-06-01)
In an important recent paper Kristensen et al. address a question of fundamental importance in plant biotechnology: how are metabolic pathways affected upon introduction of a transgene? Analysis of the transcriptome and metabolome of Arabidopsis thaliana engineered to produce the
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
Kirsten Annette Nielsen et al.
Phytochemistry, 69(1), 88-98 (2007-08-21)
Synthesis of the tyrosine derived cyanogenic glucoside dhurrin in Sorghum bicolor is catalyzed by two multifunctional, membrane bound cytochromes P450, CYP79A1 and CYP71E1, and a soluble UDPG-glucosyltransferase, UGT85B1 (Tattersall, D.B., Bak, S., Jones, P.R., Olsen, C.E., Nielsen, J.K., Hansen, M.L.
Brenda S J Winkel
Annual review of plant biology, 55, 85-107 (2005-02-24)
The organization of cooperating enzymes into macromolecular complexes is a central feature of cellular metabolism. A major advantage of such spatial organization is the transfer of biosynthetic intermediates between catalytic sites without diffusion into the bulk phase of the cell.
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