Basic information
- 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- Molecular formula
- C14H17NO7
- Average molar mass
- 311.29 g/mol
- Monoisotopic mass
- 311.10050188
Overview
(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.
Names & identifiers
- Preferred name
- Dhurrin
- IUPAC
- (2S)-2-(4-hydroxyphenyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
- English name
- DHURRIN
- Molecular formula
- C14H17NO7
- Molecular weight
- 311.29
Names & synonyms
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
Show more names
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]
Properties
Computed structural properties
- XLogP
- -0.9
- Topological polar surface area
- 143 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 4
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 403
Experimental & physicochemical properties
SpringerMaterials PropertiesChemical shift
Physicochemical properties
- Melting point
- 200 °C · 200°C (dec.)
- alpha
- 20 · D20 -65° (alc)
- Boiling point
- 586.7 · 586.7±50.0 °C(Predicted)
- Density
- 1.56 · 1.56±0.1 g/cm3(Predicted)
- storage temp.
- room temp
- pka
- 9.19 · 9.19±0.26(Predicted)
- form
- powder or crystals
- color
- 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
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
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.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- 3
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 22-45
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P264-P270-P301+P312-P330-P501
Chemistry & industry
Applications
UsesDhurrin is a cyanogenic glucoside produced by sorghum and is considered a natural defense compound producing hydrogen cyanide to deter animal herbivores.
Suppliers42 total
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
銘瑞集團有限公司17318633522 · [email protected]
上海纯优生物科技有限公司18302135232 18302135232 · [email protected]
成都埃法生物科技有限公司028-028-85142057 19983342022 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
武汉众志诚生物技术有限公司13628624121 13628604890 · [email protected]
成都普睿法药物研发有限公司82633860 18982077548 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
梯希爱（上海）化工贸易有限公司021-61109150 · [email protected]
成都普思生物科技股份有限公司028-85370565-229 18080489829 · [email protected]
Related reactions
2 records
Compound notes
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