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Category: cosmetic agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Food Chemicals Codex Listed: | No |
| Soluble in: |
| | water, 2.688e+005 mg/L @ 25 °C (est) |
Organoleptic Properties:
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| Odor and/or flavor descriptions from others (if found). |
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Cosmetic Information:
Suppliers:
Safety Information:
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
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Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | cosmetic agents |
| Recommendation for prunasin usage levels up to: | | | not for fragrance use.
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| 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 |
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 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
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 |
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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