2-methyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanenitrile

• ChemBase ID: 153535
• Molecular Formular: C10H17NO6
• Molecular Mass: 247.24508
• Monoisotopic Mass: 247.10558727
• SMILES: CC(C)(C#N)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](OC(C#N)(C)C)[C@@H]([C@H]([C@@H]1O)O)O
• 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
• InChIKey: QLTCHMYAEJEXBT-ZEBDFXRSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanenitrile
• IUPAC Traditional name: linamarin
• Synonyms: 2-(β-D-Glucopyranosyloxy)-2-methyl-propanenitrile; Phaseolunatin; Linamarin; α-Hydroxyisobutyronitrile β-D-glucopyranoside; α-Hydroxyisobutyronitrile β-D-glucose; 2-(β-D-Glucopyranosyloxy)-2-methylpropionitrile; Linamarin; α-Hydroxyisobutyronitrile β-D-glucopyranoside; Linamarin; α-Hydroxyisobutyronitrile β-D-glucopyranoside

Database IDs

• CAS Number: 554-35-8
• MDL Number: MFCD00036209
• PubChem SID: 162247674
• PubChem CID: 11128

CALCULATED PROPERTIES

• Acid pKa: 12.208436
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.7519505
• LogD (pH = 7.4): -1.7519572
• Log P: -1.7519504
• Molar Refractivity: 54.9457 cm^3
• Polarizability: 22.366673 Å^3
• Polar Surface Area: 123.17 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 142-143°C
• Optical Rotation: [α]/D -25.5±1.5°, c = 1 in H2O

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Acid Sensitive
• RTECS: TZ4850000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/22-36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H332-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥97%; ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C10H17NO6

DETAILS

Sigma Aldrich - 68264

Biochem/physiol Actions
Linamarin is a cyanogenic glucoside found in the leaves and roots of plants such as cassava, lima beans, and flax. Upon exposure to enzymes and gut flora in the human intestine, linamarin and its methylated relative lotaustralin can decompose to the toxic chemical hydrogen cyanide
Application
Linamarin, a cyanogenic glucose substrate, is used together with β-glucosidase, linamarase, to produce cyanide in vivo as a potential anticancer strategy.

Toronto Research Chemicals - L466000

Can be found in the seed skins and embryos of flax.