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CAS Number: 554-35-8Picture of molecule3D/inchi
Nikkaji Web:J6.462I
Beilstein Number:0019237
XlogP3:-1.80 (est)
Molecular Weight:247.24769000
Formula:C10 H17 N O6
NMR Predictor:Predict (works with chrome, Edge 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
Soluble in:
 water, 5.649e+005 mg/L @ 25 °C (est)
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
Cosmetic Information:
None found
BOC Sciences
For experimental / research use only.
Santa Cruz Biotechnology
For experimental / research use only.
Linamarin ≥97%
Sigma-Aldrich: Sigma
For experimental / research use only.
a-Hydroxyisobutyronitrile β-D-glucopyranoside ≥98.0% (HPLC)
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
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
Safety in Use Information:
natural substances and extractives
Recommendation for linamarin usage levels up to:
 not for fragrance use.
Recommendation for linamarin flavor usage levels up to:
 not for flavor use.
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :11128
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
RTECS:TZ4850000 for cas# 554-35-8
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):11128
Pubchem (cas):554-35-8
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
KEGG (GenomeNet):C01594
HMDB (The Human Metabolome Database):HMDB33699
VCF-Online:VCF Volatile Compounds in Food
Potential Blenders and core components note
None Found
Potential Uses:
None Found
Occurrence (nature, food, other):note
 linum usitatissimum
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 manihot utilissimus
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 phaseolus lunatus
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 trifolium repens
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1-cyano-1-methylethyl beta-D-glucoside
 propanenitrile, 2-(beta-D-glucopyranosyloxy)-2-methyl-


PubMed:From malt to wheat beer: A comprehensive multi-toxin screening, transfer assessment and its influence on basic fermentation parameters.
PubMed:Honeybees Tolerate Cyanogenic Glucosides from Clover Nectar and Flowers.
PubMed:Spatial separation of the cyanogenic β-glucosidase ZfBGD2 and cyanogenic glucosides in the haemolymph ofZygaenalarvae facilitates cyanide release.
PubMed:Effects of acetone cyanohydrin, a derivative of cassava, on motor activity and kidney and liver function in Wistar rats.
PubMed:Cyanogen Metabolism in Cassava Roots: Impact on Protein Synthesis and Root Development.
PubMed:Secoisolariciresinol Diglucoside and Cyanogenic Glycosides in Gluten-free Bread Fortified with Flaxseed Meal.
PubMed:In vitro assessment of the genotoxic and cytotoxic effects of boiled juice (tucupi) from Manihot esculenta Crantz roots.
PubMed:Differential phenotypic and genetic expression of defence compounds in a plant-herbivore interaction along elevation.
PubMed:Resilience of cassava (Manihot esculenta Crantz) to salinity: implications for food security in low-lying regions.
PubMed:The protective effect of two commercial formats of Ginkgo biloba on motor alterations induced by cassava juice (Manihot esculenta Crantz) in Wistar rats.
PubMed:Harvesting the biosynthetic machineries that cultivate a variety of indispensable plant natural products.
PubMed:Contribution of hippocampal area CA1 to acetone cyanohydrin-induced loss of motor coordination in rats.
PubMed:Lotus japonicus flowers are defended by a cyanogenic β-glucosidase with highly restricted expression to essential reproductive organs.
PubMed:A recycling pathway for cyanogenic glycosides evidenced by the comparative metabolic profiling in three cyanogenic plant species.
PubMed:Synthesis and Characterization of Hapten-Protein Conjugates for Antibody Production against Cyanogenic Glycosides.
PubMed:Dirigent Protein-Mediated Lignan and Cyanogenic Glucoside Formation in Flax Seed: Integrated Omics and MALDI Mass Spectrometry Imaging.
PubMed:Analysis of different strategies adapted by two cassava cultivars in response to drought stress: ensuring survival or continuing growth.
PubMed:Motor impairments induced by microinjection of linamarin in the dorsal hippocampus of Wistar rats.
PubMed:Quantitation of multiple mycotoxins and cyanogenic glucosides in cassava samples from Tanzania and Rwanda by an LC-MS/MS-based multi-toxin method.
PubMed:A standardized extract of Ginkgo biloba prevents locomotion impairment induced by cassava juice in Wistar rats.
PubMed:Chemical defense balanced by sequestration and de novo biosynthesis in a lepidopteran specialist.
PubMed:[Determination method of linamarin in cassava products and beans by ultra high performance liquid chromatography with tandem mass spectrometry].
PubMed:Variation in cyanogenic glycosides across populations of wild lima beans (Phaseolus lunatus) has no apparent effect on bruchid beetle performance.
PubMed:The evolutionary appearance of non-cyanogenic hydroxynitrile glucosides in the Lotus genus is accompanied by the substrate specialization of paralogous β-glucosidases resulting from a crucial amino acid substitution.
PubMed:Transcriptional regulation of de novo biosynthesis of cyanogenic glucosides throughout the life-cycle of the burnet moth Zygaena filipendulae (Lepidoptera).
PubMed:Ultraperformance liquid chromatography tandem mass spectrometry determination of cyanogenic glucosides in Trifolium species.
PubMed:Memory deficits associated with sublethal cyanide poisoning relative to cyanate toxicity in rodents.
PubMed:Sequestration, tissue distribution and developmental transmission of cyanogenic glucosides in a specialist insect herbivore.
PubMed:In vitro degradation of poly (D, L-lactide-co-glycolide) nanoparticles loaded with linamarin.
PubMed:[Evaluation of an analytical method for cyanogenic compounds in bean paste and its application for surveillance of real samples].
PubMed:Male-to-female transfer of 5-hydroxytryptophan glucoside during mating in Zygaena filipendulae (Lepidoptera).
PubMed:[Chemical constituents from the linseed meal].
PubMed:Neurotoxic effect of linamarin in rats associated with cassava (Manihot esculenta Crantz) consumption.
PubMed:Antioxidative polyphenols from Nigerian mistletoe Loranthus micranthus (Linn.) parasitizing on Hevea brasiliensis.
PubMed:Light affects in vitro organogenesis ofLinum usitatissimumL. and its cyanogenic potential.
PubMed:Screening for Bacillus subtilis group isolates that degrade cyanogens at pH 4.5-5.0.
PubMed:Rubber (Hevea brasiliensis) seed oil toxicity effect and Linamarin compound analysis.
PubMed:Biosynthesis of rhodiocyanosides in Lotus japonicus: rhodiocyanoside A is synthesized from (Z)-2-methylbutanaloxime via 2-methyl-2-butenenitrile.
PubMed:Toxicity and delivery methods for the linamarase/linamarin/glucose oxidase system, when used against human glioma tumors implanted in the brain of nude rats.
PubMed:Overexpression of hydroxynitrile lyase in cassava roots elevates protein and free amino acids while reducing residual cyanogen levels.
PubMed:Characterization and expression profile of two UDP-glucosyltransferases, UGT85K4 and UGT85K5, catalyzing the last step in cyanogenic glucoside biosynthesis in cassava.
PubMed:A survey of total hydrocyanic acid content in ready-to-eat cassava-based chips obtained in the Australian market in 2008.
PubMed:Moisture-pressure combination treatments for cyanide reduction in grated cassava.
PubMed:Convergent evolution in biosynthesis of cyanogenic defence compounds in plants and insects.
PubMed:Cyanogenic glucosides in the biological warfare between plants and insects: the Burnet moth-Birdsfoot trefoil model system.
PubMed:Neurological disorders associated with cassava diet: a review of putative etiological mechanisms.
PubMed:Therapy mediated by mitophagy abrogates tumor progression.
PubMed:Strategies for elimination of cyanogens from cassava for reducing toxicity and improving food safety.
PubMed:Biosynthesis of the cyanogenic glucosides linamarin and lotaustralin in cassava: isolation, biochemical characterization, and expression pattern of CYP71E7, the oxime-metabolizing cytochrome P450 enzyme.
PubMed:Tri-trophic level impact of host plant linamarin and lotaustralin on Tetranychus urticae and its predator Phytoseiulus persimilis.
PubMed:Cassava: an appraisal of its phytochemistry and its biotechnological prospects.
PubMed:On the biomarkers and mechanisms of konzo, a distinct upper motor neuron disease associated with food (cassava) cyanogenic exposure.
PubMed:Genetic screening identifies cyanogenesis-deficient mutants of Lotus japonicus and reveals enzymatic specificity in hydroxynitrile glucoside metabolism.
PubMed:The retail market for fresh cassava root tubers in the European Union (EU): the case of Copenhagen, Denmark--a chemical food safety issue?
PubMed:Constituents and secondary metabolite natural products in fresh and deteriorated cassava roots.
PubMed:An efficient treatment for detoxification process of cassava starch by plant cell wall-degrading enzymes.
PubMed:The targets of acetone cyanohydrin neurotoxicity in the rat are not the ones expected in an animal model of konzo.
PubMed:A straightforward method for the colorimetric detection of endogenous biological cyanide.
PubMed:In vitro degradation of linamarin by microorganisms isolated from cassava wastewater treatment lagoons.
PubMed:The adenovirus-mediated linamarase/linamarin suicide system: a potential strategy for the treatment of hepatocellular carcinoma.
PubMed:The leaf, inner bark and latex cyanide potential of Hevea brasiliensis: evidence for involvement of cyanogenic glucosides in rubber yield.
PubMed:Autophagy induction as an efficient strategy to eradicate tumors.
PubMed:Leaching of cyanogenic glucosides and cyanide from white clover green manure.
PubMed:The beta-glucosidases responsible for bioactivation of hydroxynitrile glucosides in Lotus japonicus.
PubMed:Glioma regression in vitro and in vivo by a suicide combined treatment.
PubMed:[The killing effect and bystander effect of linamarase/linamarin suicide gene system on human hepatocellular carcinoma cell line HepG2 in vitro].
PubMed:Transgenic approaches for cyanogen reduction in cassava.
PubMed:Intimate roles for cyanogenic glucosides in the life cycle of Zygaena filipendulae (Lepidoptera, Zygaenidae).
PubMed:Cytotoxicity of purified cassava linamarin to a selected cancer cell lines.
PubMed:Linamarase activities in Bacillus spp. responsible for thermophilic aerobic digestion of agricultural wastes for animal nutrition.
PubMed:The cyanogenic glucoside composition of Zygaena filipendulae (Lepidoptera: Zygaenidae) as effected by feeding on wild-type and transgenic lotus populations with variable cyanogenic glucoside profiles.
PubMed:Over-expression of hydroxynitrile lyase in transgenic cassava roots accelerates cyanogenesis and food detoxification.
PubMed:The Unitarian Hypothesis for the aetiology of diabetes mellitus.
PubMed:Therapeutic protein transduction of mammalian cells and mice by nucleic acid-free lentiviral nanoparticles.
PubMed:Purification and characterization of an intracellular beta-glucosidase from the methylotrophic yeast Pichia pastoris.
PubMed:Cassava plants with a depleted cyanogenic glucoside content in leaves and tubers. Distribution of cyanogenic glucosides, their site of synthesis and transport, and blockage of the biosynthesis by RNA interference technology.
PubMed:Engineering cyanogen synthesis and turnover in cassava (Manihot esculenta).
PubMed:A geminivirus-induced gene silencing system for gene function validation in cassava.
PubMed:Neurochemical and behavioural correlates in cassava-induced neurotoxicity in rats.
PubMed:[The canine model in the gene therapy of glioblastoma].
PubMed:Biosynthesis of the nitrile glucosides rhodiocyanoside A and D and the cyanogenic glucosides lotaustralin and linamarin in Lotus japonicus.
PubMed:Cassava cyanogens and fish mercury are high but safely consumed in the diet of native Amazonians.
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:Cyanogenic potential in cassava and its influence on a generalist insect herbivore Cyrtomenus bergi (Hemiptera: Cydnidae).
PubMed:Generation of cyanogen-free transgenic cassava.
PubMed:New aspects in pathogenesis of konzo: neural cell damage directly caused by linamarin contained in cassava (Manihot esculenta Crantz).
PubMed:Fish are central in the diet of Amazonian riparians: should we worry about their mercury concentrations?
PubMed:Linamarase expression in cassava cultivars with roots of low- and high-cyanide content.
PubMed:Cyanide bystander effect of the linamarase/linamarin killer-suicide gene therapy system.
PubMed:Loss of residual cyanogens in a cassava food during short-term storage.
PubMed:Antibody-guided enzyme therapy of cancer producing cyanide results in necrosis of targeted cells.
PubMed:Effect of yam (Dioscorea cayenensis) and dasheen (Colocassia esculenta) extracts on the kidney of streptozotocin-induced diabetic rats.
PubMed:Characterization of sucrose uptake system in cassava (Manihot esculenta Crantz).
PubMed:High cassava production and low dietary cyanide exposure in mid-west Nigeria.
PubMed:Identification of essential active-site residues in the cyanogenic beta-glucosidase (linamarase) from cassava (Manihot esculenta Crantz) by site-directed mutagenesis.
PubMed:New chemiluminescence assay for linamarin.
PubMed:Low dietary cyanogen exposure from frequent consumption of potentially toxic cassava in Malawi.
PubMed:Cloning, expression, characterization, and nucleophile identification of family 3, Aspergillus niger beta-glucosidase.
PubMed:Cytochromes P-450 from cassava (Manihot esculenta Crantz) catalyzing the first steps in the biosynthesis of the cyanogenic glucosides linamarin and lotaustralin. Cloning, functional expression in Pichia pastoris, and substrate specificity of the isolated recombinant enzymes.
PubMed:Degradation of cyanogenic glycosides by Lactobacillus plantarum strains from spontaneous cassava fermentation and other microorganisms.
PubMed:Cassava latex as a source of linamarase for determination of linamarin.
PubMed:Simple method for determination of thiocyanate in urine.
PubMed:Metabolic fates in humans of linamarin in cassava flour ingested as stiff porridge.
PubMed:Ankle clonus and thiocyanate, linamarin, and inorganic sulphate excretion in school children in communities with Konzo, Mozambique.
PubMed:Production and properties of the linamarase and amygdalase activities of Penicillium aurantiogriseum P35.
PubMed:Successful use of a plant gene in the treatment of cancer in vivo.
PubMed:Low cyanide exposure from consumption of cassava in Dar es Salaam, Tanzania.
PubMed:Cyanogenesis in cassava. The role of hydroxynitrile lyase in root cyanide production
PubMed:Beta-glycosidase (amygdalase and linamarase) from Endomyces fibuliger (LU677): formation and crude enzyme properties.
PubMed:Geographical and seasonal association between linamarin and cyanide exposure from cassava and the upper motor neurone disease konzo in former Zaire.
PubMed:Facile Synthesis of Cyanogen Glycosides (R)-Prunasin, Linamarin and (S)-Heterodendrin.
PubMed:Konzo associated with war in Mozambique.
PubMed:Linamarin sensors:  interference-based sensing of linamarin using linamarase and peroxidase.
PubMed:Toxic models of upper motor neuron disease.
PubMed:Biosynthesis of cyanohydrin glucosides from unnatural nitriles in intact tissue of Passiflora morifolia and Turnera angustifolia.
PubMed:Isolation and characterization of an enzyme with beta-glucosidase and beta-fucosidase activities from Dalbergia cochinchinensis Pierre.
PubMed:Co-purification from Escherichia coli of a plant beta-glucosidase-glutathione S-transferase fusion protein and the bacterial chaperonin GroEL.
PubMed:Sources of fungal linamarases.
PubMed:Cyanogenic and non-cyanogenic glycosides from Manihot esculenta.
PubMed:The crystal structure of a cyanogenic beta-glucosidase from white clover, a family 1 glycosyl hydrolase.
PubMed:Cyanide detoxification in cassava for food and feed uses.
PubMed:Mechanisms of increased linamarin degradation during solid-substrate fermentation of cassava.
PubMed:The adverse effects of long-term cassava (Manihot esculenta Crantz) consumption.
PubMed:A specific and sensitive method for the determination of linamarin in Urine.
PubMed:Fate in humans of dietary intake of cyanogenic glycosides from roots of sweet cassava consumed in Cuba.
PubMed:Investigation of the active site of the cyanogenic beta-D-glucosidase (linamarase) from Manihot esculenta Crantz (cassava). I. Evidence for an essential carboxylate and a reactive histidine residue in a single catalytic center.
PubMed:Analysis of the cyanogenic glycoside linamarin in urine by isotachophoresis.
PubMed:Blood and hepatic glutathione in linamarin fed rats.
PubMed:Microdiffusion method with solid state detection of cyanogenic glycosides from cassava in human urine.
PubMed:Pathological changes in growing dogs fed on a balanced cassava (Manihot esculenta Crantz) diet.
PubMed:High alpha-linolenic acid flaxseed (Linum usitatissimum): some nutritional properties in humans.
PubMed:Effects of different rates of drying cassava root on its toxicity to broiler chicks.
PubMed:Changes in cassava toxicity during processing into gari and ijapu--two fermented food products.
PubMed:Characterization ofgari andfu-fu preparation procedures in Nigeria.
PubMed:The biosynthesis of cyanogenic glucosides in seedlings of cassava (Manihot esculenta Crantz).
PubMed:The metabolism of a natural product: lessons learned from cyanogenic glycosides.
PubMed:The toxic effects of cassava (manihot esculenta grantz) diets on humans: a review.
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:Purification, characterization, and localization of linamarase in cassava.
PubMed:Cyanoglycoside gynocardin fromAcraea horta (L.) (Lepidoptera: Acraeinae) : Possible implications for evolution of acraeine host choice.
PubMed:Intermediary metabolic changes in rabbits administered linamarin or potassium cyanide.
PubMed:Metabolism of linamarin in rats.
PubMed:Pattern of enzyme changes in rabbits administered linamarin or potassium cyanide.
PubMed:An analysis of the costs and benefits of the cyanogenic system in Trifolium repens L.
PubMed:Characterization of cyanogenic beta-glucosidase (linamarase) from cassava (Manihot esculenta Crantz).
PubMed:Mobilization and utilization of cyanogenic glycosides: the linustatin pathway.
PubMed:Synthesis of the cyanogenic beta-glucosidase, linamarase, in white clover.
PubMed:Cyanogenesis and the role of cyanogenic compounds in insects.
PubMed:Cyanogenesis-a general phenomenon in the lepidoptera?
PubMed:The Linamarin beta-Glucosidase in Costa Rican Wild Lima Beans (Phaseolus lunatus L.) Is Apoplastic.
PubMed:Purification and properties of beta-D-glucosidase (linamarase) from the butter bean, Phaseolus lunatus.
PubMed:Hevea Linamarase-A Nonspecific beta-Glycosidase.
PubMed:Linamarin and histamine in the defense of adultZygaena filipendulae.
PubMed:Biliary excretion of linamarin in the Wistar rat after a single dose.
PubMed:Comparative metabolism of linamarin and amygdalin in hamsters.
PubMed:Isolation and characterization of two cyanogenic beta-glucosidases from flax seeds.
PubMed:Linamarase and other β-glucosidases are present in the cell walls of Trifolium repens L. leaves.
PubMed:Developmental toxicity of the cyanogenic glycoside linamarin in the golden hamster.
PubMed:Properties of a microsomal enzyme system from Linum usitatissimum (linen flax) which oxidizes valine to acetone cyanohydrin and isoleucine to 2-methylbutanone cyanohydrin.
PubMed:Effect of thiamin status on the metabolism of linamarin in rats.
PubMed:Cuticular cavities: storage chambers for cyanoglucoside-containing defensive secretions in larvae of a Zygaenid moth.
PubMed:Hydrolysis of linamarin by intestinal bacteria.
PubMed:Electrochemical detection of cyanogenic glycosides after enzymatic post-column cleavage.
PubMed:Cyanogenic Glycosides from Triticum monococcum.
PubMed:Spectrophotometric determination of cyanoglucosides in cassava.
PubMed:The inheritance of cyanoglucoside content in Trifolium repens L.
PubMed:Qualitative and quantitative studies on the compounds of the larval defensive secretion of Zygaena trifolii (Esper, 1783) (Insecta, Lepidoptera, Zygaenidae).
PubMed:Cyanide in human disease: a review of clinical and laboratory evidence.
PubMed:Sugar and organic Acid constituents in white clover.
PubMed:Changes of cyanide content and linamarase activity in wounded cassava roots.
PubMed:In vitro characterization of the Ac locus in white clover (Trifolium repens L.).
PubMed:Cyanogenesis in Passifloraceae.
PubMed:[The occurrence of hydrocyanic acid in Cormophytes. 18th. Communication. New observations in leguminosae-Papilionoideae (Galegeae, Genisteae, Loteae, Phaseoleae)].
PubMed:Influence of dose level and methionine intake on the effects of linamarin administration to rats.
PubMed:Cyanogenic glycosides in butterflies: detection and synthesis of linamarin and lotaustralin in the heliconiinae.
PubMed:Isolation of factors in linseed oil meal protective against chronic selenosis in rats.
PubMed:Effect of linamarin on thiocyanate production and thyroid activity in rats.
PubMed:Physiological and biochemical changes associated with linamarin administration to rats.
PubMed:Fate of orally dosed linamarin in the rat.
PubMed:Determination of linamarin in biological tissues.
PubMed:The origin of the glucosidic linkage oxygen of the cyanogenic glucosides, linamarin and lotaustralin.
PubMed:Oximes, nitriles and 2-hydroxynitriles as precursors in the biosynthesis of cyanogenic glucosides.
PubMed:Plasma amino-acids in the Nigerian nutritional ataxic neuropathy.
PubMed:Origin of cyanide in cultures of a psychrophilic basidiomycete.
PubMed:Conversion of alpha-keto-isovaleric acid oxime and isobutyraldoxime to linamarin in flax seedlings.
PubMed:The isolation, properties, and enzymic breakdown of linamarin from cassava.
PubMed:[Linamarin content of healthy and of Colletotrichum lini infected, young flax plants].
PubMed:[Flax tuber linamarin].
PubMed:[Linamarin of lin seed and its determination].
None found
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