Grundinformationen
- CAS
499-20-7- Standard-SMILES
N#C[C@@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)c1ccc(O)cc1- InChIKey
NVLTYOJHPBMILU-YOVYLDAJSA-N- Summenformel
- C14H17NO7
- Durchschnittliche Molmasse
- 311,29 g/mol
- Monoisotopische Masse
- 311,10050188
Überblick
(S)-4-hydroxymandelonitrile beta-D-glucoside is a beta-D-glucoside consisting of (S)-prunasin carrying a hydroxy substituent at position 4 on the phenyl ring. It is a nitrile, a beta-D-glucoside, a cyanogenic glycoside and a monosaccharide derivative. It is functionally related to a (S)-prunasin.
Namen und Bezeichner
- Bevorzugter Name
- Dhurrin
- IUPAC
- (2S)-2-(4-hydroxyphenyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
- Lokaler Name
- (S)-(β-D-Glucopyranosyloxy)(4-hydroxyphenyl)acetonitril
- Englischer Name
- DHURRIN
- Summenformel
- C14H17NO7
- Molmasse
- 311.29
Namen und Synonyme
Dhurrin499-20-7P5999IY65C(S)-4-Hydroxymandelonitrile beta-D-glucoside(2S)-2-(4-hydroxyphenyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile(2S)-(beta-D-glucopyranosyloxy)(4-hydroxyphenyl)acetonitrileCHEBI:27826DTXSID90198142(alphaS)-alpha-(beta-D-glucopyranosyloxy)-4-hydroxybenzeneacetonitrile(S)-p-Hydroxymandelnitrile-beta-D-glucopyranoside(2S)-2-(4-hydroxyphenyl)-2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyacetonitrileRefChem:132456
Weitere Namen anzeigen
C05143DHURRIN(RG)CYANOGLUCOSIDEDHURRIN USP/EP/BPDhurrin >=95% (HPLC)Highly unstable in solutionP-HYDROXYMANDELONITRILE-B-D-GLUCOSIDE4-HYDROXYMANDELONITRILE-BETA-D-GLUCOSIDEP-HYDROXYMANDELONITRILE-BETA-D-GLUCOSIDE
DTXCID20120633207-878-6(S)-(beta-D-Glucopyranosyloxy)(4-hydroxyphenyl)acetonitrileC14H17NO7MFCD18632527UNII-P5999IY65CEINECS 207-878-6DHURRIN [MI]
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,9
- Polarare Oberfläche (TPSA)
- 143 Ų
- H-Brücken-Donoren
- 5
- H-Brücken-Akzeptoren
- 8
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 22
- Formalladung
- 0
- Komplexität
- 403
Experimentelle und physikochemische Eigenschaften
SpringerMaterials PropertiesChemical shift
Physikochemische Eigenschaften
- Schmelzpunkt
- 200 °C · 200°C (dec.)
- Siedepunkt
- 586.7 · 586.7±50.0 °C(Predicted)
- Dichte
- 1.56 · 1.56±0.1 g/cm3(Predicted)
- storage temp.
- room temp
- pka
- 9.19 · 9.19±0.26(Predicted)
- Aggregatzustand
- powder or crystals
- Farbe
- white to light brown
- 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-/m1/s1
- InChIKey
- NVLTYOJHPBMILU-YOVYLDAJSA-N
- SMILES
- OC[C@H]1O[C@@H](O[C@H](C#N)c2ccc(O)cc2)[C@H](O)[C@@H](O)[C@@H]1O || OC[C@H]1O[C@@H](O[C@H](C#N)c2ccc(O)cc2)[C@H](O)[C@@H](O)[C@@H]1O
- LogP
- -1.65 · -1.650 (est)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 1 notifications to the ECHA C&L Inventory.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Sicherheitsdaten
- wgk
- 3
- risk_code
- 22
- hazard_code
- Xn
- safety_code
- 22-45
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Acute Tox. 4 Oral
Chemie und Industrie
Anwendungen
VerwendenDhurrin is a cyanogenic glucoside produced by sorghum and is considered a natural defense compound producing hydrogen cyanide to deter animal herbivores.
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