Record Information |
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Version |
1.0 |
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Update Date |
1/22/2018 11:54:54 AM |
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Metabolite ID | PAMDB120484 |
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Identification |
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Name: |
taxiphyllin |
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Description: | A β-D-glucoside consisting of (R)-prunasin carrying a hydroxy substituent at position 4 on the phenyl ring. |
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Structure |
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Synonyms: | - (R)-4-Hydroxymandelonitrile beta-D-glucoside
- (R)-alpha-(β-D-glucopyranosyloxy)-4-hydroxybenzeneacetonitrile
- (R)-p-hydroxymandelonitrile-D-glucopyranoside
- Taxiphyllin
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Chemical Formula: |
C14H17NO7 |
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Average Molecular Weight: |
311.291 |
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Monoisotopic Molecular
Weight: |
311.1005 |
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InChI Key: |
NVLTYOJHPBMILU-GMDXDWKASA-N |
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InChI: | InChI=1S/C14H17NO7/c15-5-9(7-1-3-8(17)4-2-7)21-14-13(20)12(19)11(18)10(6-16)22-14/h1-4,9-14,16-20H,6H2/t9-,10+,11+,12-,13+,14+/m0/s1 |
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CAS
number: |
21401-21-8 |
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IUPAC Name: | (2R)-(β-D-glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile |
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Traditional IUPAC Name: |
dhurrin |
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SMILES: | C(C(C1(C=CC(=CC=1)O))OC2(OC(C(C(C2O)O)O)CO))#N |
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Chemical Taxonomy |
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Taxonomy Description | This compound belongs to the class of chemical entities known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. |
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Kingdom |
Chemical entities |
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Super Class | Organic compounds |
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Class |
Organic oxygen compounds |
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Sub Class | Organooxygen compounds |
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Direct Parent |
Cyanogenic glycosides |
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Alternative Parents |
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Substituents |
- Cyanogenic glycoside
- Hexose monosaccharide
- O-glycosyl compound
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Monocyclic benzene moiety
- Monosaccharide
- Oxane
- Benzenoid
- Secondary alcohol
- Polyol
- Oxacycle
- Nitrile
- Carbonitrile
- Acetal
- Organoheterocyclic compound
- Organonitrogen compound
- Hydrocarbon derivative
- Alcohol
- Organopnictogen compound
- Organic nitrogen compound
- Primary alcohol
- Aromatic heteromonocyclic compound
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Molecular Framework |
Aromatic heteromonocyclic compounds |
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External Descriptors |
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Physical Properties |
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State: |
Not Available |
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Charge: | 0 |
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Melting point: |
176 °C |
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Experimental Properties: |
Property | Value | Reference |
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Melting Point | 176 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties |
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Biological Properties |
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Cellular Locations: |
Not Available |
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Reactions: | |
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Pathways: |
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Spectra |
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Spectra: |
Spectrum Type | Description | Splash Key | |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0w29-0922000000-4323039c23c09ae7d5b6 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ue9-0900000000-20291a7cc72858475773 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ff0-2900000000-d9b8829840517b5ef00a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03dj-1927000000-2051e5cb0bd7423a8dad | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-2910000000-abc72215556e260df8c0 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0007-8900000000-11bb86435bb0e9209de4 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0w29-0922000000-4323039c23c09ae7d5b6 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ue9-0900000000-20291a7cc72858475773 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ff0-2900000000-d9b8829840517b5ef00a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03dj-1927000000-2051e5cb0bd7423a8dad | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-2910000000-abc72215556e260df8c0 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0007-8900000000-11bb86435bb0e9209de4 | View in MoNA |
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References |
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References: |
- Petruccioli M, Brimer L, Cicalini AR, Pulci V, Federici F (1999)Production and properties of the linamarase and amygdalase activities of Penicillium aurantiogriseum P35. Bioscience, biotechnology, and biochemistry 63, Pubmed: 10380623
- Calderón AI, Terreaux C, Gupta MP, Hostettmann K, Schenk KJ (2003)Taxiphyllin from Henriettella fascicularis. Acta crystallographica. Section C, Crystal structure communications 59, Pubmed: 12711800
- Rosen MA, Farnden KJ, Conn EE (1975)Stereochemical aspects of the biosynthesis of the epimeric cyanogenic glucosides dhurrin and taxiphyllin. The Journal of biological chemistry 250, Pubmed: 1194256
- Nahrstedt A, Kant JD, Hösel W (1984)Aspects on the Biosynthesis of the Cyanogenic Glucoside Triglochinin in Triglochin maritima1. Planta medica 50, Pubmed: 17340339
- Cutler AJ, Hösel W, Sternberg M, Conn EE (1981)The in vitro biosynthesis of taxiphyllin and the channeling of intermediates in Triglochin maritima. The Journal of biological chemistry 256, Pubmed: 7012151
- Oueslati MH, Ben Jannet H, Mighri Z, Chriaa J, Abreu PM (2006)Phytochemical constituents from Salsola tetrandra. Journal of natural products 69, Pubmed: 16989538
- Hösel W, Nahrstedt A (1980)In vitro biosynthesis of the cyanogenic glucoside taxiphyllin in Triglochin maritima. Archives of biochemistry and biophysics 203, Pubmed: 7458352
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Synthesis Reference: |
Not Available |
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Material Safety Data Sheet (MSDS) |
Not Available |
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Links |
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External Links: |
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