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Linamarin

CAS No.:
554-35-8
Catalog Number:
AG00D7WX
Molecular Formula:
C10H17NO6
Molecular Weight:
247.2451
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥98%
1 week
United States
$91
- +
5mg
≥98%
1 week
United States
$126
- +
10mg
≥98%
1 week
United States
$179
- +
25mg
≥98%
1 week
United States
$318
- +
Product Description
Catalog Number:
AG00D7WX
Chemical Name:
Linamarin
CAS Number:
554-35-8
Molecular Formula:
C10H17NO6
Molecular Weight:
247.2451
MDL Number:
MFCD00036209
IUPAC Name:
2-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropanenitrile
InChI:
InChI=1S/C10H17NO6/c1-10(2,4-11)17-9-8(15)7(14)6(13)5(3-12)16-9/h5-9,12-15H,3H2,1-2H3/t5-,6-,7+,8-,9+/m1/s1
InChI Key:
QLTCHMYAEJEXBT-ZEBDFXRSSA-N
SMILES:
OC[C@H]1O[C@@H](OC(C#N)(C)C)[C@@H]([C@H]([C@@H]1O)O)O
UNII:
H3V9RP3WLO
Properties
Complexity:
311  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Defined Bond Stereocenter Count:
0
Exact Mass:
247.106g/mol
Formal Charge:
0
Heavy Atom Count:
17  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
247.247g/mol
Monoisotopic Mass:
247.106g/mol
Rotatable Bond Count:
3  
Topological Polar Surface Area:
123A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.8  
Literature
Title Journal
Biosynthesis of rhodiocyanosides in Lotus japonicus: rhodiocyanoside A is synthesized from (Z)-2-methylbutanaloxime via 2-methyl-2-butenenitrile. Phytochemistry 20120501
Rubber (Hevea brasiliensis) seed oil toxicity effect and Linamarin compound analysis. Lipids in health and disease 20120101
Toxicity and delivery methods for the linamarase/linamarin/glucose oxidase system, when used against human glioma tumors implanted in the brain of nude rats. Cancer letters 20111226
Transcriptome sequencing of Hevea brasiliensis for development of microsatellite markers and construction of a genetic linkage map. DNA research : an international journal for rapid publication of reports on genes and genomes 20111201
Characterization and expression profile of two UDP-glucosyltransferases, UGT85K4 and UGT85K5, catalyzing the last step in cyanogenic glucoside biosynthesis in cassava. The Plant journal : for cell and molecular biology 20111001
Cyanogenic glucosides in the biological warfare between plants and insects: the Burnet moth-Birdsfoot trefoil model system. Phytochemistry 20110901
A survey of total hydrocyanic acid content in ready-to-eat cassava-based chips obtained in the Australian market in 2008. Journal of food protection 20110601
Konzo: from poverty, cassava, and cyanogen intake to toxico-nutritional neurological disease. PLoS neglected tropical diseases 20110601
Therapy mediated by mitophagy abrogates tumor progression. Autophagy 20110501
Convergent evolution in biosynthesis of cyanogenic defence compounds in plants and insects. Nature communications 20110401
On the biomarkers and mechanisms of konzo, a distinct upper motor neuron disease associated with food (cassava) cyanogenic exposure. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20110301
Strategies for elimination of cyanogens from cassava for reducing toxicity and improving food safety. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20110301
Neurological disorders associated with cassava diet: a review of putative etiological mechanisms. Metabolic brain disease 20110301
Biosynthesis of the cyanogenic glucosides linamarin and lotaustralin in cassava: isolation, biochemical characterization, and expression pattern of CYP71E7, the oxime-metabolizing cytochrome P450 enzyme. Plant physiology 20110101
Transgenic biofortification of the starchy staple cassava (Manihot esculenta) generates a novel sink for protein. PloS one 20110101
Medicinal plants used as antitumor agents in Brazil: an ethnobotanical approach. Evidence-based complementary and alternative medicine : eCAM 20110101
Moisture-pressure combination treatments for cyanide reduction in grated cassava. Journal of food science 20110101
A genome scan for quantitative trait loci affecting cyanogenic potential of cassava root in an outbred population. BMC genomics 20110101
Overexpression of hydroxynitrile lyase in cassava roots elevates protein and free amino acids while reducing residual cyanogen levels. PloS one 20110101
Study of the effects of hydrogen cyanide exposure in Cassava workers. Indian journal of occupational and environmental medicine 20110101
Cassava: an appraisal of its phytochemistry and its biotechnological prospects. Phytochemistry 20101201
Tri-trophic level impact of host plant linamarin and lotaustralin on Tetranychus urticae and its predator Phytoseiulus persimilis. Journal of chemical ecology 20101201
Research into mercury exposure and health education in subsistence fish-eating communities of the Amazon basin: potential effects on public health policy. International journal of environmental research and public health 20100901
Naturally occurring food toxins. Toxins 20100901
Genetic screening identifies cyanogenesis-deficient mutants of Lotus japonicus and reveals enzymatic specificity in hydroxynitrile glucoside metabolism. The Plant cell 20100501
Constituents and secondary metabolite natural products in fresh and deteriorated cassava roots. Phytochemistry 20100401
The adenovirus-mediated linamarase/linamarin suicide system: a potential strategy for the treatment of hepatocellular carcinoma. Cancer letters 20100328
The retail market for fresh cassava root tubers in the European Union (EU): the case of Copenhagen, Denmark--a chemical food safety issue? Journal of the science of food and agriculture 20100130
The targets of acetone cyanohydrin neurotoxicity in the rat are not the ones expected in an animal model of konzo. Neurotoxicology and teratology 20100101
An efficient treatment for detoxification process of cassava starch by plant cell wall-degrading enzymes. Journal of bioscience and bioengineering 20100101
Biosynthesis of 2-hydroxyisobutyric acid (2-HIBA) from renewable carbon. Microbial cell factories 20100101
A straightforward method for the colorimetric detection of endogenous biological cyanide. Analytical chemistry 20091115
Cyanogenesis of wild lima bean (Phaseolus lunatus L.) is an efficient direct defence in nature. PloS one 20090101
454 pyrosequencing based transcriptome analysis of Zygaena filipendulae with focus on genes involved in biosynthesis of cyanogenic glucosides. BMC genomics 20090101
Autophagy induction as an efficient strategy to eradicate tumors. Autophagy 20081001
The beta-glucosidases responsible for bioactivation of hydroxynitrile glucosides in Lotus japonicus. Plant physiology 20080701
Leaching of cyanogenic glucosides and cyanide from white clover green manure. Chemosphere 20080601
[The killing effect and bystander effect of linamarase/linamarin suicide gene system on human hepatocellular carcinoma cell line HepG2 in vitro]. Xi bao yu fen zi mian yi xue za zhi = Chinese journal of cellular and molecular immunology 20080301
Glioma regression in vitro and in vivo by a suicide combined treatment. Molecular cancer research : MCR 20080301
Intimate roles for cyanogenic glucosides in the life cycle of Zygaena filipendulae (Lepidoptera, Zygaenidae). Insect biochemistry and molecular biology 20071101
Cytotoxicity of purified cassava linamarin to a selected cancer cell lines. Bioprocess and biosystems engineering 20070701
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. Insect biochemistry and molecular biology 20070101
Linamarase activities in Bacillus spp. responsible for thermophilic aerobic digestion of agricultural wastes for animal nutrition. Waste management (New York, N.Y.) 20070101
Transgenic approaches for cyanogen reduction in cassava. Journal of AOAC International 20070101
Sequencing analysis of 20,000 full-length cDNA clones from cassava reveals lineage specific expansions in gene families related to stress response. BMC plant biology 20070101
The Unitarian Hypothesis for the aetiology of diabetes mellitus. Medical hypotheses 20060101
Purification and characterization of an intracellular beta-glucosidase from the methylotrophic yeast Pichia pastoris. Biochemistry. Biokhimiia 20051201
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. Plant physiology 20050901
A geminivirus-induced gene silencing system for gene function validation in cassava. Plant molecular biology 20041101
Engineering cyanogen synthesis and turnover in cassava (Manihot esculenta). Plant molecular biology 20041101
Biosynthesis of the nitrile glucosides rhodiocyanoside A and D and the cyanogenic glucosides lotaustralin and linamarin in Lotus japonicus. Plant physiology 20040501
Cassava cyanogens and fish mercury are high but safely consumed in the diet of native Amazonians. Ecotoxicology and environmental safety 20040301
Raman spectroscopic analysis of cyanogenic glucosides in plants: development of a flow injection surface-enhanced Raman scatter (FI-SERS) method for determination of cyanide. Applied spectroscopy 20040201
Over-expression of hydroxynitrile lyase in transgenic cassava roots accelerates cyanogenesis and food detoxification. Plant biotechnology journal 20040101
Cyanogenic potential in cassava and its influence on a generalist insect herbivore Cyrtomenus bergi (Hemiptera: Cydnidae). Journal of economic entomology 20031201
New aspects in pathogenesis of konzo: neural cell damage directly caused by linamarin contained in cassava (Manihot esculenta Crantz). The British journal of nutrition 20030801
Fish are central in the diet of Amazonian riparians: should we worry about their mercury concentrations? Environmental research 20030701
Generation of cyanogen-free transgenic cassava. Planta 20030701
[The canine model in the gene therapy of glioblastoma]. Anales de la Real Academia Nacional de Medicina 20030101
Linamarase expression in cassava cultivars with roots of low- and high-cyanide content. Plant physiology 20020801
Loss of residual cyanogens in a cassava food during short-term storage. International journal of food sciences and nutrition 20020701
Cyanide bystander effect of the linamarase/linamarin killer-suicide gene therapy system. The journal of gene medicine 20020101
Effect of yam (Dioscorea cayenensis) and dasheen (Colocassia esculenta) extracts on the kidney of streptozotocin-induced diabetic rats. International journal of food sciences and nutrition 20010901
High cassava production and low dietary cyanide exposure in mid-west Nigeria. Public health nutrition 20010201
Identification of essential active-site residues in the cyanogenic beta-glucosidase (linamarase) from cassava (Manihot esculenta Crantz) by site-directed mutagenesis. The Biochemical journal 20010115
Properties