dhurrin
(S)-p-hydroxymandelnitrile-beta-D-glucopyranoside
 
Notes:
cyanogenic glucoside from plant sorghum; (r)-epimer is taxiphyllin. Cyanogenic glucoside isol. from Sorghum vulgare (sorghum) Dhurrin is a cyanogenic glycoside occurring in plants. Its biosynthesis has been elucidated. Dhurrin is hydrolyzed in the stomach of an insect into a carbohydrate and aglycone. The aglycone is unstable and releases hydrogen cyanide.
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CAS Number: 499-20-7Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 207-878-6
FDA UNII: P5999IY65C
Nikkaji Web: J10.589I
MDL: MFCD18632527
XlogP3-AA: -0.90 (est)
Molecular Weight: 311.29089000
Formula: C14 H17 N O7
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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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)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
ExtraSynthese
For experimental / research use only.
Dhurrin (HPLC) ≥90%
Sigma-Aldrich: Sigma
For experimental / research use only.
Dhurrin ≥95% (HPLC)
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
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.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 161355
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 (2S)-2-(4-hydroxyphenyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
Chemidplus: 0000499207
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References:
 (2S)-2-(4-hydroxyphenyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 161355
Pubchem (sid): 135065619
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
KEGG (GenomeNet): C05143
HMDB (The Human Metabolome Database): HMDB30704
FooDB: FDB002626
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 borage plant
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 macadamia leaf
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 sorghum
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 sorghum vulgare
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 wheat sprout
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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
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Articles:
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.
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