(2R)-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: 72917
• 分子式: C20H27NO11
• 平均质量: 457.42848
• 单一同位素质量: 457.15841069
• SMILES: [C@H]1([C@H]([C@@H](O[C@@H]([C@H]1O)CO)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@H](c1ccccc1)C#N)O)O)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](O[C@H](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+/m0/s1
• InChIKey: XUCIJNAGGSZNQT-JHSLDZJXSA-N

名称和登记号

名称

• IUPAC标准名: (2R)-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: vitamin B17; laetrile
• 别名: Amygdaloside; Glucoprunasin; Amygdalin; Amygdalin

登记号

• CAS号: 29883-15-6
• EC号: 249-925-3
• PubChem SID: 162037837
• PubChem CID: 656516; 34751
• CHEBI ID: 17019
• CHEMBL: 461727
• Chemspider ID: 570897
• 医学主题词(MeSH): Amygdalin
• 美国药典/FDA物质标识码: 214UUQ9N0H
• 维基百科标题: Amygdalin

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

• 外观: Powder

安全信息

• 保存条件: -20°C
• RTECS编号: OO8450000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 危险公开号: R:22
• 安全公开号: S:36/37/39
• NFPA704:
  

  0

  1

  0

产品相关信息

• 成盐信息: Free Base
• 分类: Genuine Natural Compounds

详细说明

MP Biomedicals - 05202055

MP Biomedicals Rare Chemical collection

Selleck Chemicals - S2260

Research Area: Cancer
Biological Activity:
Amygdalin is a glycoside initially isolated from the seeds of the tree Prunus dulcis, also known as bitter almonds. The metabolism of amygdalin produces hydrogen cyanide, a potent toxin. Beta-glucosidase, one of the enzymes that catalyzes the release of cyanide from amygdalin, is present in human small intestine and in a variety of common foods. This leads to an unpredictable and potentially lethal toxicity when amygdalin or laetrile is taken orally. Ingestion of purified amygdalin or apricot seeds can cause severe toxicity and death due to cyanide poisoning. Numerous case reports in the medical literature describe serious cyanide poisoning in patients who ingested laetrile as a cancer treatment. [1] 

参考文献

• http://en.wikipedia.org/wiki/Amygdalin