prunasin
benzeneacetonitrile, alpha-(beta-D-glucopyranosyloxy)-,
Identification
| Name | prunasin |
| IUPAC | (2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile |
| CAS Number | 99-19-3 |
| FDA UNII | 14W4BPM5FB |
| Molecular Formula | C14 H17 N O6 |
| Molecular Weight | 295.29169000 |
| Nikkaji Number | J113.483C |
| Beilstein | 0091509 |
Regulatory
Physical Properties
| Food Chemicals Codex Listed | No |
| Soluble in | water, 2.688e+005 mg/L @ 25 °C (est) |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | skin conditioning |
No sensory data available
Safety Information
| 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 | 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. |
No supplier data available
Potential Uses
Natural Occurrence
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
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 2â³-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.