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

• ChemBase编号: 106097
• 分子式: C20H27NO11
• 平均质量: 457.42848
• 单一同位素质量: 457.15841069
• SMILES: c1ccc(cc1)C(C#N)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC(c3ccccc3)C#N)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C20H27NO11/c21-6-10(9-4-2-1-3-5-9)30-20-18(28)16(26)14(24)12(32-20)8-29-19-17(27)15(25)13(23)11(7-22)31-19/h1-5,10-20,22-28H,7-8H2/t10?,11-,12-,13-,14-,15+,16+,17-,18-,19-,20-/m1/s1
• InChIKey: XUCIJNAGGSZNQT-SWRVSKMJSA-N

名称和登记号

名称

• IUPAC标准名: 2-phenyl-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile
• IUPAC传统名: amygdalin
• 别名: D-扁桃腈-β-龙胆二糖苷; D-扁桃腈6-O-β-D-葡糖基-β-D-葡萄糖苷; D-杏仁腈β-龙胆二糖苷; 扁桃苷; 苦杏仁苷; D-苦杏苷; 扁桃苷; D-Mandelonitrile β-gentiobioside; D-Mandelonitrile 6-O-β-D-glucosido-β-D-glucoside; D-Mandelonitrile-β-gentiobioside; Amygdalin; Laetrile; D-Amygdalin; Amygdalin; D-Mandelonitrile 6-O-β-D-glucosido-β-D-glucoside, D-Mandelonitrile β-gentiobioside; D-AMYGLADIN

登记号

• CAS号: 29883-15-6
• EC号: 249-925-3
• MDL号: MFCD00006598
• Beilstein号: 66856
• PubChem SID: 162087187; 24846528; 24891046
• PubChem CID: 34751

理论计算性质

• Acid pKa: 11.9090805
• 质子受体: 12
• 质子供体: 7
• LogD (pH = 5.5): -2.587887
• LogD (pH = 7.4): -2.5879002
• Log P: -2.5878868
• 摩尔折射率: 102.5097 cm^3
• 极化性: 41.94759 Å^3
• 极化表面积: 202.32 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: H2O: soluble0.1 g/mL, clear to very faintly turbid, colorless (hot)
• 熔点: 210-215 °C; 223-226 °C(lit.)
• 比旋光度: [α]20/D -39±2°, c = 2% in H2O; [α]22/D -38°, c = 1.2 in H2O

安全信息

• 保存条件: Room Temperature (15-30°C)
• RTECS编号: OO8450000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22; R:22
• 安全公开号: 26-36/37/39-45; S:20-46-36/37/39
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

产品相关信息

• 纯度: ≥97.0% (HPLC); ≥99%
• 痕量阳离子: Ca: ≤30 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤300 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• 痕量阴离子: chloride (Cl-): ≤50 mg/kg; sulfate (SO42-): ≤300 mg/kg
• 生物来源: from apricot kernels
• 干燥失重: ≤5% loss on drying, 110 °C
• 产品质量级别: PREMIUM
• 产品线: BioXtra
• Empirical Formula (Hill Notation): C20H27NO11

详细说明

Sigma Aldrich - 10050

Biochem/physiol Actions
Cyanogenic glycoside that is a component of bitter almonds and apricot pits. There is no scientific evidence that amygdalin itself is an effective anti-cancer agent. Recent studies using β-glucoside linked to a tumor-associated monoclonal antibody to release cyanide at the tumor cell has shown significant cytotoxicity.
Other Notes
Review: Cyanogenic glycosides1
Application
Amygdalin, a cyanide containing glycoside, may be used as a substrate to identify, differentiate and characterize enzymes such as maltase(s), emulsin(s) and β-glucosidase(s).

Sigma Aldrich - A6005

Biochem/physiol Actions
Cyanogenic glycoside that is a component of bitter almonds and apricot pits. There is no scientific evidence that amygdalin itself is an effective anti-cancer agent. Recent studies using β-glucoside linked to a tumor-associated monoclonal antibody to release cyanide at the tumor cell has shown significant cytotoxicity.
Application
Amygdalin, a cyanide containing glycoside, may be used as a substrate to identify, differentiate and characterize enzymes such as maltase(s), emulsin(s) and β-glucosidase(s).

Sigma Aldrich - A83202

Biochem/physiol Actions
生氰糖苷是苦杏仁与杏核的成分之一。尚无科学证明显示苦杏苷是一种有效的抗癌剂。最近的研究将 β-葡萄糖苷结合到肿瘤相关单克隆抗体，以针对肿瘤细胞释放氰化物，结果表现出显著的细胞毒性。