dhurrin
(S)-p-hydroxymandelnitrile-beta-D-glucopyranoside
Identification
| Name | dhurrin |
| IUPAC | (2S)-2-(4-hydroxyphenyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile |
| CAS Number | 499-20-7 |
| EINECS | 207-878-6 |
| FDA UNII | P5999IY65C |
| Molecular Formula | C14 H17 N O7 |
| Molecular Weight | 311.29089000 |
| MDL Number | MFCD18632527 |
| Nikkaji Number | J10.589I |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 200.00 °C. @ 760.00 mm Hg |
| Boiling Point | 586.70 °C. @ 760.00 mm Hg (est) |
| Flash Point | 587.00 °F. TCC ( 308.60 °C. ) (est) |
| logP (o/w) | -1.650 (est) |
| Soluble in | water, 1e+006 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for dhurrin usage levels up to | not for fragrance use. |
| Recommendation for dhurrin flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
benzeneacetonitrile, alpha-(beta-D-glucopyranosyloxy)-4-hydroxy-, (alphaS)-
(S)-(beta-D-
glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile
(S)-p-
hydroxymandelnitrile-beta-D-glucopyranoside
(2S)-2-(4-
hydroxyphenyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
PubMed:
The necrotrophic effector protein SnTox3 re-programs metabolism and elicits a strong defence response in susceptible wheat leaves.
PubMed:
Age versus stage: does ontogeny modify the effect of phosphorus and arbuscular mycorrhizas on above- and below-ground defence in forage sorghum?
PubMed:
Effects of PEG-induced osmotic stress on growth and dhurrin levels of forage sorghum.
PubMed:
High basal defense gene expression determines sorghum resistance to the whorl-feeding insect southwestern corn borer.
PubMed:
Amygdalin analogues inhibit IFN-γ signalling and reduce the inflammatory response in human epidermal keratinocytes.
PubMed:
Forward genetics by genome sequencing reveals that rapid cyanide release deters insect herbivory of Sorghum bicolor.
PubMed:
Amphipol trapping of a functional CYP system.
PubMed:
The rare cyanogen proteacin, and dhurrin, from foliage of Polyscias australiana, a tropical Araliaceae.
PubMed:
Visualizing metabolite distribution and enzymatic conversion in plant tissues by desorption electrospray ionization mass spectrometry imaging.
PubMed:
Sorghum allelopathy--from ecosystem to molecule.
PubMed:
Global transcriptome analysis reveals distinct expression among duplicated genes during sorghum-interaction.
PubMed:
Drying and processing protocols affect the quantification of cyanogenic glucosides in forage sorghum.
PubMed:
Turning the 'mustard oil bomb' into a 'cyanide bomb': aromatic glucosinolate metabolism in a specialist insect herbivore.
PubMed:
A combined biochemical screen and TILLING approach identifies mutations in Sorghum bicolor L. Moench resulting in acyanogenic forage production.
PubMed:
A simple analytical method for dhurrin content evaluation in cyanogenic plants for their utilization in fodder and biofumigation.
PubMed:
Homology modeling of the three membrane proteins of the dhurrin metabolon: catalytic sites, membrane surface association and protein-protein interactions.
PubMed:
Comparison of gas chromotography, spectrophotometry and near infrared spectroscopy to quantify prussic acid potential in forages.
PubMed:
Plant science. Dynamic metabolons.
PubMed:
Primary or secondary? Versatile nitrilases in plant metabolism.
PubMed:
Evolution of heteromeric nitrilase complexes in Poaceae with new functions in nitrile metabolism.
PubMed:
Metabolon formation in dhurrin biosynthesis.
PubMed:
Rate of hydrolysis and degradation of the cyanogenic glycoside - dhurrin - in soil.
PubMed:
Consequences of transferring three sorghum genes for secondary metabolite (cyanogenic glucoside) biosynthesis to grapevine hairy roots.
PubMed:
Reconstitution of cyanogenesis in barley (Hordeum vulgare L.) and its implications for resistance against the barley powdery mildew fungus.
PubMed:
Determination of catalytic key amino acids and UDP sugar donor specificity of the cyanohydrin glycosyltransferase UGT85B1 from Sorghum bicolor. Molecular modeling substantiated by site-specific mutagenesis and biochemical analyses.
PubMed:
Cyanogenic glycosides and menisdaurin from Guazuma ulmifolia, Ostrya virgininana, Tiquilia plicata and Tiquilia canescens.
PubMed:
Tailoring the plant metabolome without a loose stitch.
PubMed:
Predictive metabolic engineering in plants: still full of surprises.
PubMed:
Metabolic channeling in plants.
PubMed:
Metabolic engineering of dhurrin in transgenic Arabidopsis plants with marginal inadvertent effects on the metabolome and transcriptome.
PubMed:
Structural determinants of substrate specificity in family 1 beta-glucosidases: novel insights from the crystal structure of sorghum dhurrinase-1, a plant beta-glucosidase with strict specificity, in complex with its natural substrate.
PubMed:
Raman spectroscopic analysis of cyanogenic glucosides in plants: development of a flow injection surface-enhanced Raman scatter (FI-SERS) method for determination of cyanide.
PubMed:
The in vitro substrate regiospecificity of recombinant UGT85B1, the cyanohydrin glucosyltransferase from Sorghum bicolor.
PubMed:
Mutational and structural analysis of aglycone specificity in maize and sorghum beta-glucosidases.
PubMed:
Dhurrin synthesis in sorghum is regulated at the transcriptional level and induced by nitrogen fertilization in older plants.
PubMed:
Relationship Between Levels of Cyanide in Sudangrass Hybrids Incorporated into Soil and Suppression of Meloidogyne hapla.
PubMed:
Characterization of transgenic Arabidopsis thaliana with metabolically engineered high levels of p-hydroxybenzylglucosinolate.
PubMed:
Resistance to an herbivore through engineered cyanogenic glucoside synthesis.
PubMed:
Metabolism of tyrosine and tryptophan--new genes for old pathways.
PubMed:
The mechanism of substrate (aglycone) specificity in beta -glucosidases is revealed by crystal structures of mutant maize beta -glucosidase-DIMBOA, -DIMBOAGlc, and -dhurrin complexes.
PubMed:
Transgenic tobacco and Arabidopsis plants expressing the two multifunctional sorghum cytochrome P450 enzymes, CYP79A1 and CYP71E1, are cyanogenic and accumulate metabolites derived from intermediates in Dhurrin biosynthesis.
PubMed:
The aglycone specificity-determining sites are different in 2, 4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA)-glucosidase (Maize beta -glucosidase) and dhurrinase (Sorghum beta -glucosidase).
PubMed:
Metabolic engineering of p-hydroxybenzylglucosinolate in Arabidopsis by expression of the cyanogenic CYP79A1 from Sorghum bicolor.
PubMed:
The UDP-glucose:p-hydroxymandelonitrile-O-glucosyltransferase that catalyzes the last step in synthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor. Isolation, cloning, heterologous expression, and substrate specificity.
PubMed:
Production and properties of the linamarase and amygdalase activities of Penicillium aurantiogriseum P35.
PubMed:
Substrate specificity of the cytochrome P450 enzymes CYP79A1 and CYP71E1 involved in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench.
PubMed:
The presence of CYP79 homologues in glucosinolate-producing plants shows evolutionary conservation of the enzymes in the conversion of amino acid to aldoxime in the biosynthesis of cyanogenic glucosides and glucosinolates.
PubMed:
Cloning of three A-type cytochromes P450, CYP71E1, CYP98, and CYP99 from Sorghum bicolor (L.) Moench by a PCR approach and identification by expression in Escherichia coli of CYP71E1 as a multifunctional cytochrome P450 in the biosynthesis of the cyanogenic glucoside dhurrin.
PubMed:
Isolation and reconstitution of cytochrome P450ox and in vitro reconstitution of the entire biosynthetic pathway of the cyanogenic glucoside dhurrin from sorghum.
PubMed:
Dhurrin-6'-glucoside, a cyanogenic diglucoside from Sorghum bicolor.
PubMed:
The primary sequence of cytochrome P450tyr, the multifunctional N-hydroxylase catalyzing the conversion of L-tyrosine to p-hydroxyphenylacetaldehyde oxime in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench.
PubMed:
Purification and characterization of recombinant cytochrome P450TYR expressed at high levels in Escherichia coli.
PubMed:
Cytochrome P-450TYR is a multifunctional heme-thiolate enzyme catalyzing the conversion of L-tyrosine to p-hydroxyphenylacetaldehyde oxime in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench.
PubMed:
Characterization of cytochrome P450TYR, a multifunctional haem-thiolate N-hydroxylase involved in the biosynthesis of the cyanogenic glucoside dhurrin.
PubMed:
Isolation of the heme-thiolate enzyme cytochrome P-450TYR, which catalyzes the committed step in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench.
PubMed:
Molecular cloning of hydroxynitrile lyase from Sorghum bicolor (L.). Homologies to serine carboxypeptidases.
PubMed:
The metabolism of a natural product: lessons learned from cyanogenic glycosides.
PubMed:
Involvement of Cytochrome P-450 in the Biosynthesis of Dhurrin in Sorghum bicolor (L.) Moench.
PubMed:
2-nitro-3-(p-hydroxyphenyl)propionate and aci-1-nitro-2-(p-hydroxyphenyl)ethane, two intermediates in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench.
PubMed:
The biosynthesis of cyanogenic glucosides in higher plants. Identification of three hydroxylation steps in the biosynthesis of dhurrin in Sorghum bicolor (L.) Moench and the involvement of 1-ACI-nitro-2-(p-hydroxyphenyl)ethane as an intermediate.
PubMed:
Turnover of dhurrin in green sorghum seedlings.
PubMed:
Larvicidal effects of grain sorghum (Sorghum bicolor) seedling extracts upon Culex pipiens larvae.
PubMed:
The biosynthesis of cyanogenic glucosides in higher plants. The (E)- and (Z)-isomers of p-hydroxyphenylacetaldehyde oxime as intermediates in the biosynthesis of dhurrin in Sorghum bicolor (L.) Moench.
PubMed:
Biosynthesis of the Cyanogenic Glucoside Dhurrin in Seedlings of Sorghum bicolor (L.) Moench and Partial Purification of the Enzyme System Involved.
PubMed:
Allelopathic potential of sorghum-sudangrass hybrid (sudex).
PubMed:
Cyanogenic glucosides: the biosynthetic pathway and the enzyme system involved.
PubMed:
Characterization of beta-glucosidases with high specificity for the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) moench seedlings.
PubMed:
Relationship between contents of leucoanthocyanidin and dhurrin in sorghum leaves.
PubMed:
Hydrolysis of a naturally occurring beta-glucoside by a broad-specificity beta-glucosidase from liver.
PubMed:
In-vitro biosynthesis of 1-(4'-hydroxyphenyl)-2-nitroethane and production of cyanogenic compounds in osmotically stressed cell suspension cultures of Eschscholtzia californica Cham.
PubMed:
Leakage of Dhurrin and p-Hydroxybenzaldehyde from Young Sorghum Shoots Immersed in Various Solvents.
PubMed:
[The occurrence of hydrocyanic acid in Cormophytes. 18th. Communication. New observations in leguminosae-Papilionoideae (Galegeae, Genisteae, Loteae, Phaseoleae)].
PubMed:
Subcellular Localization of Dhurrin beta-Glucosidase and Hydroxynitrile Lyase in the Mesophyll Cells of Sorghum Leaf Blades.
PubMed:
Aphid feeding deterrents in sorghum : Bioassay isolation and characterization.
PubMed:
[The cyanogenic glycosides of triticum, secale and sorghum].
PubMed:
The biosynthesis of cyanogenic glucosides in higher plants. Channeling of intermediates in dhurrin biosynthesis by a microsomal system from Sorghum bicolor (linn) Moench.
PubMed:
The biosynthesis of cyanogenic glucosides in higher plants. N-Hydroxytyrosine as an intermediate in the biosynthesis of dhurrin by Sorghum bicolor (Linn) Moench.
PubMed:
Tissue Distributions of Dhurrin and of Enzymes Involved in Its Metabolism in Leaves of Sorghum bicolor.
PubMed:
Presence of the cyanogenic glucoside dhurrin in isolated vacuoles from sorghum.
PubMed:
Localization of Cinnamic Acid 4-Monooxygenase and the Membrane-bound Enzyme System for Dhurrin Biosynthesis in Sorghum Seedlings.
PubMed:
Subcellular localization of the cyanogenic glucoside of sorghum by autoradiography.
PubMed:
Stereochemical aspects of the biosynthesis of the epimeric cyanogenic glucosides dhurrin and taxiphyllin.
PubMed:
The in vitro biosynthesis of dhurrin, the cyanogenic glycoside of Sorghum bicolor.
PubMed:
Biosynthesis of phenolic compounds in first internodes of sorghum: lignin and related products.
PubMed:
The metabolism of aromatic compounds in higher plants. VII. The origin of the nitrile nitrogen atom of dhurrin (beta-D-glucopyranosyloxy-L-p-hydroxymandelonitrile).
PubMed:
The metabolism of aromatic compounds in higher plants. VI. Studies on the biosynthesis of dhurrin, the cyanogenic glucoside of Sorghum vulgare.