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3952-98-5 | SINIGRIN
CAS No: 3952-98-5 Catalog No: AG003U9V MDL No:MFCD00006616
Product Description
Catalog Number:
AG003U9V
Chemical Name:
SINIGRIN
CAS Number:
3952-98-5
Molecular Formula:
C10H18KNO10S2
Molecular Weight:
415.4789
MDL Number:
MFCD00006616
IUPAC Name:
potassium;[(E)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylbut-3-enylideneamino] sulfate
InChI:
InChI=1S/C10H17NO9S2.K/c1-2-3-6(11-20-22(16,17)18)21-10-9(15)8(14)7(13)5(4-12)19-10;/h2,5,7-10,12-15H,1,3-4H2,(H,16,17,18);/q;+1/p-1/b11-6+;/t5-,7-,8+,9-,10+;/m1./s1
InChI Key:
QKFAFSGJTMHRRY-OCFLFPRFSA-M
SMILES:
C=CC/C(=N\OS(=O)(=O)[O-])/S[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O.O.[K+]
EC Number:
223-545-8
Properties
Complexity:
509
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
2
Defined Atom Stereocenter Count:
5
Defined Bond Stereocenter Count:
1
Exact Mass:
396.99g/mol
Formal Charge:
0
Heavy Atom Count:
23
Hydrogen Bond Acceptor Count:
11
Hydrogen Bond Donor Count:
4
Isotope Atom Count:
0
Molecular Weight:
397.454g/mol
Monoisotopic Mass:
396.99g/mol
Rotatable Bond Count:
7
Topological Polar Surface Area:
203A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
Literature
| Title | Journal |
|---|---|
| Sinigrin attenuates the progression of atherosclerosis in ApoE(-/-) mice fed a high-cholesterol diet potentially by inhibiting VCAM-1 expression. | Chemico-biological interactions 20170625 |
| Comparative study between extraction techniques and column separation for the quantification of sinigrin and total isothiocyanates in mustard seed. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20120715 |
| Inhibition of Listeria monocytogenes on bologna sausages by an antimicrobial film containing mustard extract or sinigrin. | International journal of food microbiology 20120501 |
| Influence of NaCl and NaNO3 on sinigrin hydrolysis by foodborne bacteria. | Journal of food protection 20111201 |
| Protein modeling and active site binding mode interactions of myrosinase-sinigrin in Brassica juncea--an in silico approach. | Journal of molecular graphics & modelling 20110201 |
| Optimization of ultrasonic-stimulated solvent extraction of sinigrin from Indian mustard seed (Brassica Juncea L.) using response surface methodology. | Phytochemical analysis : PCA 20110101 |
| Allyl isothiocyanate-rich mustard seed powder inhibits bladder cancer growth and muscle invasion. | Carcinogenesis 20101201 |
| Multidirectional time-dependent effect of sinigrin and allyl isothiocyanate on metabolic parameters in rats. | Plant foods for human nutrition (Dordrecht, Netherlands) 20100901 |
| Determination of sinigrin in vegetable seeds by online microdialysis sampling coupled to reverse-phase ion-pair liquid chromatography. | Journal of agricultural and food chemistry 20100428 |
| Monitoring the enzymatic degradation of sinigrin from B. juncea meal using (1)H NMR spectroscopy. | Natural product research 20100101 |
| [Determination of sinigrin in semen Thlaspi from Sichuan and Tibet using near infrared diffuse reflectance spectroscopy]. | Guang pu xue yu guang pu fen xi = Guang pu 20091001 |
| Updated glucosinolate profile of Dithyrea wislizenii. | Journal of natural products 20090522 |
| Interactive effects of sulfur and nitrogen supply on the concentration of sinigrin and allyl isothiocyanate in Indian mustard (Brassica juncea L.). | Journal of agricultural and food chemistry 20090513 |
| Myrosinases from root and leaves of Arabidopsis thaliana have different catalytic properties. | Phytochemistry 20090101 |
| Class targeted metabolomics: ESI ion trap screening methods for glucosinolates based on MSn fragmentation. | Phytochemistry 20080501 |
| A chemical trait creates a genetic trade-off between intra- and interspecific competitive ability. | Ecology 20080501 |
| Influence of cooking duration of cabbage and presence of colonic microbiota on the excretion of N-acetylcysteine conjugates of allyl isothiocyanate and bioactivity of phase 2 enzymes in F344 rats. | The British journal of nutrition 20080401 |
| Accumulation of glucosinolates by the cabbage aphid Brevicoryne brassicae as a defense against two coccinellid species. | Journal of chemical ecology 20080301 |
| Community complexity drives patterns of natural selection on a chemical defense of Brassica nigra. | The American naturalist 20080201 |
| The cabbage aphid: a walking mustard oil bomb. | Proceedings. Biological sciences 20070922 |
| Mutual feedbacks maintain both genetic and species diversity in a plant community. | Science (New York, N.Y.) 20070914 |
| Effects of two bitter substances on olfactory conditioning in the moth Heliothis virescens. | The Journal of experimental biology 20070701 |
| Improved hydrophilic interaction chromatography method for the identification and quantification of glucosinolates. | Journal of chromatography. A 20070622 |
| Specialist and generalist herbivores exert opposing selection on a chemical defense. | The New phytologist 20070101 |
| Changes in glucosinolate concentrations, myrosinase activity, and production of metabolites of glucosinolates in cabbage (Brassica oleracea Var. capitata) cooked for different durations. | Journal of agricultural and food chemistry 20061004 |
| Geographic patterns of herbivory and resource allocation to defense, growth, and reproduction in an invasive biennial, Alliaria petiolata. | Oecologia 20060601 |
| Two closely located areas in the suboesophageal ganglion and the tritocerebrum receive projections of gustatory receptor neurons located on the antennae and the proboscis in the moth Heliothis virescens. | The Journal of comparative neurology 20060501 |
| Sensitivity to allyl isothiocyanate, dimethyl trisulfide, sinigrin, and cooked cauliflower consumption. | Appetite 20060501 |
| Comparison of analytical and semi-preparative columns for high-performance liquid chromatography-solid-phase extraction-nuclear magnetic resonance. | Journal of chromatography. A 20060421 |
| Induction of quinone reductase by allylisothiocyanate (AITC) and the N-acetylcysteine conjugate of AITC in Hepa1c1c7 mouse hepatoma cells. | BioFactors (Oxford, England) 20060101 |
| Anti-SARS coronavirus 3C-like protease effects of Isatis indigotica root and plant-derived phenolic compounds. | Antiviral research 20051001 |
| Effects of Brussels sprout juice on the cell cycle and adhesion of human colorectal carcinoma cells (HT29) in vitro. | Journal of agricultural and food chemistry 20050518 |
| Glucosinolates in the subantarctic crucifer Kerguelen cabbage (Pringlea antiscorbutica). | Journal of natural products 20050201 |
| Use of near-infrared spectroscopy for screening the individual and total glucosinolate contents in Indian mustard seed (Brassica juncea L. Czern. & Coss.). | Journal of agricultural and food chemistry 20040602 |
| In vitro digestion of sinigrin and glucotropaeolin by single strains of Bifidobacterium and identification of the digestive products. | Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20040301 |
| Hydrolysis of glucosinolates to isothiocyanates after ingestion of raw or microwaved cabbage by human volunteers. | Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20040101 |
| Colon cancer proliferating desulfosinigrin in wasabi (Wasabia japonica). | Nutrition and cancer 20040101 |
| Evaluation of urinary N-acetyl cysteinyl allyl isothiocyanate as a biomarker for intake and bioactivity of Brussels sprouts. | Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20031201 |
| Uptake and distribution of sinigrin in microspore derived embryos of Brassica napus L. | Journal of plant physiology 20030801 |
| Is induction response negatively correlated with constitutive resistance in black mustard? | Evolution; international journal of organic evolution 20021101 |
| Flavor-active compounds potentially implicated in cooked cauliflower acceptance. | Journal of agricultural and food chemistry 20021023 |
| Direct and simultaneous analysis of sinigrin and allyl isothiocyanate in mustard samples by high-performance liquid chromatography. | Journal of agricultural and food chemistry 20020814 |
| Metabolism of sinigrin (2-propenyl glucosinolate) by the human colonic microflora in a dynamic in vitro large-intestinal model. | Carcinogenesis 20020601 |
| Evaluation of glucoiberin reference material from Iberis amara by spectroscopic fingerprinting. | Journal of natural products 20020401 |
| Spatial organization of the glucosinolate-myrosinase system in brassica specialist aphids is similar to that of the host plant. | Proceedings. Biological sciences 20020122 |
| Effects of Brussels sprouts extracts on hydrogen peroxide-induced DNA strand breaks in human lymphocytes. | Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20011201 |
| Identification of new derivatives of sinigrin and glucotropaeolin produced by the human digestive microflora using 1H NMR spectroscopy analysis of in vitro incubations. | Drug metabolism and disposition: the biological fate of chemicals 20011101 |
| In situ observation of the generation of isothiocyanates from sinigrin in horseradish and wasabi. | Biochimica et biophysica acta 20010815 |
| Direct determination of sinigrin in mustard seed without desulfatation by reversed-phase ion-pair liquid chromatography. | Journal of chromatography. A 20010406 |
| Formation of allyl isothiocyanate from sinigrin in the digestive tract of rats monoassociated with a human colonic strain of Bacteroides thetaiotaomicron. | FEMS microbiology letters 20010401 |
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