prunasin
benzeneacetonitrile, alpha-(beta-D-glucopyranosyloxy)-,
 
Notes:
Isol. from kernels of Prunus spp., immature fruits of Passiflora spp. and leaves of perilla (Perilla frutescens var. acuta)
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CAS Number: 99-19-3Picture of molecule3D/inchi
Other: 1300-20-5
FDA UNII: 14W4BPM5FB
Nikkaji Web: J113.483C
Beilstein Number: 0091509
XlogP3-AA: -0.70 (est)
Molecular Weight: 295.29169000
Formula: C14 H17 N O6
NMR Predictor: Predict (works with chrome or firefox)
Category: cosmetic agents
 
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Physical Properties:
Food Chemicals Codex Listed: No
Soluble in:
 water, 2.688e+005 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:
CosIng: cosmetic data
Cosmetic Uses: skin conditioning
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Suppliers:
 None found
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Safety Information:
 
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: cosmetic agents
Recommendation for prunasin usage levels up to:
 not for fragrance use.
 
Recommendation for prunasin 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 : 119033
National Institute of Allergy and Infectious Diseases: Data
 (2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
Chemidplus: 0000099183
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References:
 (2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 119033
Pubchem (sid): 135144538
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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
CHEMBL: View
KEGG (GenomeNet): C00844
HMDB (The Human Metabolome Database): HMDB34934
FooDB: FDB013526
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
 almond seed
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 cherry sour cherry seed
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 elder black elder
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 papaya leaf
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 passion fruit
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 peach seed
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 perilla frutescens var. acuta leaf
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Synonyms:
 benzeneacetonitrile, alpha-(beta-D-glucopyranosyloxy)-,
(R)-alpha-(beta-D-glucopyranosyloxy)benzene-acetonitrile
(2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
(R)-prunasin
D-prunasin
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Articles:
PubMed: Occurrence of Benzoic Acid Esters as Putative Catabolites of Prunasin in Senescent Leaves of Prunus laurocerasus.
PubMed: Amygdalin, quackery or cure?
PubMed: Seasonal Changes Affect Root Prunasin Concentration in Prunus serotina and Override Species Interactions between P. serotina and Quercus petraea.
PubMed: General and Stereocontrolled Approach to the Chemical Synthesis of Naturally Occurring Cyanogenic Glucosides.
PubMed: Transition of phenolics and cyanogenic glycosides from apricot and cherry fruit kernels into liqueur.
PubMed: α-Glucosidase Inhibitors from Vauquelinia corymbosa.
PubMed: A recycling pathway for cyanogenic glycosides evidenced by the comparative metabolic profiling in three cyanogenic plant species.
PubMed: Concurrent quantification and comparative pharmacokinetic analysis of bioactive compounds in the Herba Ephedrae-Semen Armeniacae Amarum herb pair.
PubMed: Severe cyanide poisoning from an alternative medicine treatment with amygdalin and apricot kernels in a 4-year-old child.
PubMed: Lignans and aromatic glycosides from Piper wallichii and their antithrombotic activities.
PubMed: Taxiphyllin 6'-O-gallate, actinidioionoside 6'-O-gallate and myricetrin 2″-O-sulfate from the leaves of Syzygium samarangense and their biological activities.
PubMed: [Qualitative and quantitative analysis of amygdalin and its metabolite prunasin in plasma by ultra-high performance liquid chromatography-tandem quadrupole time of flight mass spectrometry and ultra-high performance liquid chromatography-tandem triple quadrupole mass spectrometry].
PubMed: Identification and characterization of CYP79D16 and CYP71AN24 catalyzing the first and second steps in L-phenylalanine-derived cyanogenic glycoside biosynthesis in the Japanese apricot, Prunus mume Sieb. et Zucc.
PubMed: In Silico Investigation of Cytochrome P450 2C9 in relation to Aging Using Traditional Chinese Medicine.
PubMed: Quantitative analysis of amygdalin and prunasin in Prunus serotina Ehrh. using (1) H-NMR spectroscopy.
PubMed: Amygdalin analogues inhibit IFN-γ signalling and reduce the inflammatory response in human epidermal keratinocytes.
PubMed: Reports on the distribution of aromatic cyanogenic glycosides in Australian tropical rainforest tree species of the Lauraceae and Sapindaceae.
PubMed: Amygdalin inhibits renal fibrosis in chronic kidney disease.
PubMed: Prunasin hydrolases during fruit development in sweet and bitter almonds.
PubMed: Neuroprotective activity of galloylated cyanogenic glucosides and hydrolysable tannins isolated from leaves of Phyllagathis rotundifolia.
PubMed: Phenylalanine derived cyanogenic diglucosides from Eucalyptus camphora and their abundances in relation to ontogeny and tissue type.
PubMed: A set of two diastereomers of cyanogenic glycosides from Passiflora quadrangularis.
PubMed: A new flavonoid and other constituents from Centaurea nicaeensis All. var. walliana M.
PubMed: Characterisation of galloylated cyanogenic glucosides and hydrolysable tannins from leaves of Phyllagathis rotundifolia by LC-ESI-MS/MS.
PubMed: [Effect of processing on metabolism of amygdalin from bitter almond in rat].
PubMed: Metabolites of amygdalin under simulated human digestive fluids.
PubMed: Tissue and cellular localization of individual beta-glycosidases using a substrate-specific sugar reducing assay.
PubMed: Generation of primary amide glucosides from cyanogenic glucosides.
PubMed: A new ferulic acid ester and other constituents from Dracocephalum peregrinum.
PubMed: Inhibitory effect of amygdalin on lipopolysaccharide-inducible TNF-alpha and IL-1beta mRNA expression and carrageenan-induced rat arthritis.
PubMed: Analysis of cyanogens with resorcinol and picrate.
PubMed: A pseudo-beta-glucosidase in Arabidopsis thaliana: correction by site-directed mutagenesis, heterologous expression, purification, and characterization.
PubMed: Heterocyclic compounds from Chrysanthemum coronarium L. and their inhibitory activity on hACAT-1, hACAT-2, and LDL-oxidation.
PubMed: Frequency and distribution of cyanogenic glycosides in Eucalyptus L'Hérit.
PubMed: Two new maltol glycosides and cyanogenic glycosides from Elsholtzia rugulosa Hemsl.
PubMed: Larvae of the fall webworm, Hyphantria cunea, inhibit cyanogenesis in Prunus serotina.
PubMed: Bitterness in almonds.
PubMed: Purification and characterization of UDP-glucose : curcumin glucoside 1,6-glucosyltransferase from Catharanthus roseus cell suspension cultures.
PubMed: Ontogenetic and temporal trajectories of chemical defence in a cyanogenic eucalypt.
PubMed: Vicianin hydrolase is a novel cyanogenic beta-glycosidase specific to beta-vicianoside (6-O-alpha-L-arabinopyranosyl-beta-D-glucopyranoside) in seeds of Vicia angustifolia.
PubMed: Amygdalin induces apoptosis through regulation of Bax and Bcl-2 expressions in human DU145 and LNCaP prostate cancer cells.
PubMed: Absorption of toxic beta-glucosides produced by plants and their effect on tissue trehalases from insects.
PubMed: Purification and characterization of an intracellular beta-glucosidase from the methylotrophic yeast Pichia pastoris.
PubMed: An HPLC/MS method for identifying major constituents in the hypocholesterolemic extracts of Chinese medicine formula 'Xue-Fu-Zhu-Yu decoction'.
PubMed: Cyanogenic glycosides from the rare Australian endemic rainforest tree Clerodendrum grayi (Lamiaceae).
PubMed: Two new dammarane triterpenoids from Kageneckia angustifolia D. Don.
PubMed: Kinetics of the natural evolution of hydrogen cyanide in plants in neotropical Pteridium arachnoideum and its ecological significance.
PubMed: Cyanogenic glucosides in grapevine: polymorphism, identification and developmental patterns.
PubMed: The role of carboxyl, guanidine and imidazole groups in catalysis by a midgut trehalase purified from an insect larvae.
PubMed: Kinetic analysis of hexose transport to determine the mechanism of amygdalin and prunasin absorption in the intestine.
PubMed: Cyanogenic Eucalyptus nobilis is polymorphic for both prunasin and specific beta-glucosidases.
PubMed: Purification and characterization of vanilla bean (Vanilla planifolia Andrews) beta-D-glucosidase.
PubMed: Temporal and spatial variation in cyanogenic glycosides in Eucalyptus cladocalyx.
PubMed: Anti-tumor promoting effect of glycosides from Prunus persica seeds.
PubMed: Purification and characterization of three beta-glycosidases from midgut of the sugar cane borer, Diatraea saccharalis.
PubMed: Chromatographic determination of cyanoglycosides prunasin and amygdalin in plant extracts using a porous graphitic carbon column.
PubMed: A new acylated triterpene from the roots of Chaenomeles japonica.
PubMed: Cyanogenic allosides and glucosides from Passiflora edulis and Carica papaya.
PubMed: Investigation of the microheterogeneity and aglycone specificity-conferring residues of black cherry prunasin hydrolases.
PubMed: Cyanogenesis in glucosinolate-producing plants: Carica papaya and Carica quercifolia.
PubMed: Cucurbitacin F in seeds of Kageneckia angustifolia (Rosaceae).
PubMed: Pharmaco-toxicological study of Kageneckia oblonga, Rosaceae.
PubMed: Relationship between cyanogenic compounds in kernels, leaves, and roots of sweet and bitter kernelled almonds.
PubMed: New cyanogenic and alkyl glycoside constituents from Phyllagathis rotundifolia.
PubMed: DNA polymerase beta mediates protection of mammalian cells against ganciclovir-induced cytotoxicity and DNA breakage.
PubMed: Vicianin, prunasin, and beta-cyanoalanine in common vetch seed as sources of urinary thiocyanate in the rat.
PubMed: Characterization of sucrose uptake system in cassava (Manihot esculenta Crantz).
PubMed: Natural glycosides containing allopyranose from the passion fruit plant and circular dichroism of benzaldehyde cyanohydrin glycosides.
PubMed: Analysis of cyanogenic glycosides by micellar capillary electrophoresis.
PubMed: Degradation of cyanogenic glycosides by Lactobacillus plantarum strains from spontaneous cassava fermentation and other microorganisms.
PubMed: The cyanogenic glucoside, prunasin (D-mandelonitrile-beta-D-glucoside), is a novel inhibitor of DNA polymerase beta.
PubMed: Production and properties of the linamarase and amygdalase activities of Penicillium aurantiogriseum P35.
PubMed: Beta-glycosidase (amygdalase and linamarase) from Endomyces fibuliger (LU677): formation and crude enzyme properties.
PubMed: Amygdalin degradation by Mucor circinelloides and Penicillium aurantiogriseum: mechanisms of hydrolysis.
PubMed: Isolation of An Aroma Precursor of Benzaldehyde from Tea Leaves (Camellia sinensis var. sinensis cv. Yabukita).
PubMed: Facile Synthesis of Cyanogen Glycosides (R)-Prunasin, Linamarin and (S)-Heterodendrin.
PubMed: Isolation and characterization of an enzyme with beta-glucosidase and beta-fucosidase activities from Dalbergia cochinchinensis Pierre.
PubMed: Two-step hydrolysis of amygdalin in molds.
PubMed: Small-intestinal transfer mechanism of prunasin, the primary metabolite of the cyanogenic glycoside amygdalin.
PubMed: Cloning, sequencing, and characterization of a membrane-associated Prevotella ruminicola B(1)4 beta-glucosidase with cellodextrinase and cyanoglycosidase activities.
PubMed: Temporal and spatial expression of amygdalin hydrolase and (R)-(+)-mandelonitrile lyase in black cherry seeds.
PubMed: Black cherry poisoning in an Angora goat.
PubMed: Immunocytochemical Localization of Prunasin Hydrolase and Mandelonitrile Lyase in Stems and Leaves of Prunus serotina.
PubMed: Utilization of Amygdalin during Seedling Development of Prunus serotina.
PubMed: Tissue Level Compartmentation of (R)-Amygdalin and Amygdalin Hydrolase Prevents Large-Scale Cyanogenesis in Undamaged Prunus Seeds.
PubMed: Experimental intoxication in rats from a HCN-free extract of Holocalyx glaziovii Taub.: probable participation of the cyanogenic glycoside.
PubMed: Tissue and Subcellular Localization of Enzymes Catabolizing (R)-Amygdalin in Mature Prunus serotina Seeds.
PubMed: Prunus serotina Amygdalin Hydrolase and Prunasin Hydrolase : Purification, N-Terminal Sequencing, and Antibody Production.
PubMed: Exolytic hydrolysis of toxic plant glucosides by guinea pig liver cytosolic beta-glucosidase.
PubMed: Development of the Potential for Cyanogenesis in Maturing Black Cherry (Prunus serotina Ehrh.) Fruits.
PubMed: Continuous spectrophotometric assays for beta-glucosidases acting on the plant glucosides L-picein and prunasin.
PubMed: Pattern of the Cyanide-Potential in Developing Fruits : Implications for Plants Accumulating Cyanogenic Monoglucosides (Phaseolus lunatus) or Cyanogenic Diglucosides in Their Seeds (Linum usitatissimum, Prunus amygdalus).
PubMed: Factors that determine rates of cyanogenesis in bovine ruminal fluid in vitro.
PubMed: Catabolism of Cyanogenic Glycosides by Purified Vicianin Hydrolase from Squirrel's Foot Fern (Davallia Trichomanoides Blume).
PubMed: Behavior, Parasitism, Morphology, and Biochemistry of Criconemella xenoplax and C. ornata on Peach.
PubMed: Cyanogenesis and the role of cyanogenic compounds in insects.
PubMed: Growth and the composition and transport of carbohydrate in compatible and incompatible peach/plum grafts.
PubMed: Isolation and characterization of multiple forms of prunasin hydrolase from black cherry (Prunus serotina Ehrh.) seeds.
PubMed: Purification and properties of beta-D-glucosidase (linamarase) from the butter bean, Phaseolus lunatus.
PubMed: Toxicity of D, L-mandelonitrile-beta-D-glucoside, "prulaurasin" in rat.
PubMed: Intestinal first pass metabolism of amygdalin in the rat in vitro.
PubMed: Comparison of kinetic and molecular properties of two forms of amygdalin hydrolase from black cherry (Prunus serotina Ehrh.) seeds.
PubMed: Comparative metabolism of linamarin and amygdalin in hamsters.
PubMed: On the metabolism of amygdalin. 2. The distribution of beta-glucosidase activity and orally administered amygdalin in rats.
PubMed: Cyanogenesis of Passiflora edulis.
PubMed: [Colon cleansing: a comparative study].
PubMed: Determination of amygdalin and its major metabolite prunasin in plasma and urine by high pressure liquid chromatography.
PubMed: The pharmacokinetics of prunasin, a metabolite of amygdalin.
PubMed: The pharmacokinetics of amygdalin.
PubMed: A rapid and sensitive spectrophotometric assay for prunasin hydrolase activity employing purified mandelonitrile lyase.
PubMed: [The occurrence of hydrocyanic acid in Cormophytes. 18th. Communication. New observations in leguminosae-Papilionoideae (Galegeae, Genisteae, Loteae, Phaseoleae)].
PubMed: Amygdalin (Laetrile) and prunasin beta-glucosidases: distribution in germ-free rat and in human tumor tissue.
PubMed: [Distribution of hydrocyanic Acid in cormophyta: 15.1 new observations on cyanogenesis in Rosaceae].
PubMed: A beta-glucosidase in feline kidney that hydrolyzes amygdalin (laetrile).
PubMed: Screening test for amygdalin in tablets, solutions, powders, and seeds.
PubMed: Oximes, nitriles and 2-hydroxynitriles as precursors in the biosynthesis of cyanogenic glucosides.
PubMed: The enzymic hydrolysis of amygdalin.
PubMed: Biosynthesis of Prunasin, the Cyanogenic Glucoside of Peach.
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