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

• ChemBase编号: 153535
• 分子式: C10H17NO6
• 平均质量: 247.24508
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 2-methyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanenitrile
• IUPAC传统名: linamarin
• 别名: α-Hydroxyisobutyronitrile β-D-glucopyranoside; 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

登记号

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

理论计算性质

• Acid pKa: 12.208436
• 质子受体: 7
• 质子供体: 4
• LogD (pH = 5.5): -1.7519505
• LogD (pH = 7.4): -1.7519572
• Log P: -1.7519504
• 摩尔折射率: 54.9457 cm^3
• 极化性: 22.366673 Å^3
• 极化表面积: 123.17 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Methanol; Water
• 外观: White Solid
• 熔点: 142-143°C
• 比旋光度: [α]/D -25.5±1.5°, c = 1 in H2O

安全信息

• 保存条件: -20°C Freezer, Under Inert Atmosphere
• 保存注意事项: Acid Sensitive
• RTECS编号: TZ4850000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 20/22-36/37/38
• 安全公开号: 26-36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H315-H319-H332-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: -20°C; 2-8°C

产品相关信息

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

详细说明

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.