Structure via PubChem · Public domain (PubChem)
(R)-amygdalin
Sign in to saveAlso known as D-mandelonitrile-beta-D-glucosido-6-beta-D-glucoside, D-(-)-mandelonitrile-beta-D-gentiobioside, D-amygdalin, (2R)-2-phenyl-2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylol-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-acetonitrile, (2R)-2-phenyl-2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-acetonitrile, (2R)-2-phenyl-2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-ethanenitrile, (2R)-2-phenyl-2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-acetonitrile
Amygdalin (from Ancient Greek: '''' 'almond') is a naturally occurring chemical compound found in many plants, most notably in the seeds (kernels, pips or stones) of apricots, bitter almonds, apples, peaches, cherries and plums, and in the roots of manioc.
OverviewAI-generated
(R)-amygdalin is a chemical compound with the formula C₂₀H₂₇NO₁₁. Its mass is listed as 457.158411, while its weight is recorded as 457.4. The substance has a charge of 0, an xlogp value of -2.7, and a tpsa of 202. It contains 7 hydrogen bond donors and 12 hydrogen bond acceptors.
The compound is identified by the NCI Thesaurus ID C28801 and the PubChem CID 656516. Its canonical SMILES string is C1=CC=C(C=C1)C(C#N)OC2C(C(C(C(O2)COC3C(C(C(C(O3)CO)O)O)O)O)O, and its isomeric SMILES is OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](O[C@@H](C#N)C3=CC=CC=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O. The InChIKey for (R)-amygdalin is XUCIJNAGGSZNQT-JHSLDZJXSA-N.
There are 11 PubMed entries associated with the query for (R)-amygdalin. Additionally, the compound is referenced by 316 other encyclopedia articles.
Synthesized by Vinony from 17 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Chemical data
- Formula
- C20H27NO11
- Molecular weight
- 457.4 g/mol
- IUPAC name
- (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]oxymethyl]oxan-2-yl]oxyacetonitrile
- SMILES
- C1=CC=C(C=C1)[C@H](C#N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)O
- InChIKey
- XUCIJNAGGSZNQT-JHSLDZJXSA-N
- XLogP
- -2.7
- Polar surface area
- 202 Ų
- H-bond donors
- 7
- H-bond acceptors
- 12
- Formal charge
- 0
via PubChem
Research
11 papers- Tissue Level Compartmentation of (R)-Amygdalin and Amygdalin Hydrolase Prevents Large-Scale Cyanogenesis in Undamaged Prunus Seeds.Plant physiology · 1994
- Temporal and spatial expression of amygdalin hydrolase and (R)-(+)-mandelonitrile lyase in black cherry seeds.Plant physiology · 1995
- Problems and Pitfalls in the Analysis of Amygdalin and Its Epimer.Journal of agricultural and food chemistry · 2015
- Tissue and Subcellular Localization of Enzymes Catabolizing (R)-Amygdalin in Mature Prunus serotina Seeds.Plant physiology · 1992
- Utilization of Amygdalin during Seedling Development of Prunus serotina.Plant physiology · 1994
via PubMed
~13 min read
Encyclopedic overview
10 sectionsContents
- Sources
- Chemistry
- Laetrile
- History of laetrile
- Early usage
- Subsequent results
- Advocacy and legality of laetrile
- See also
- References
- External links
{{Chembox |Verifiedfields = changed |Watchedfields = changed |verifiedrevid = 477175041 |ImageFile = Amygdalin structure.svg |ImageClass = skin-invert-image |ImageFile2 = Amygdalin-from-xtal-3D-balls.png |ImageClass2 = bg-transparent |ImageSize2 = 220px |IUPACName = (2R)-[β-D-Glucopyranosyl-(1→6)-β-D-glucopyranosyloxy]phenylacetonitrile |SystematicName = (2R)-Phenyl{[(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 |Section1= |Section2= |Section3= |Section8= }}
Amygdalin (from Ancient Greek: '''' 'almond') is a naturally occurring chemical compound found in many plants, most notably in the seeds (kernels, pips or stones) of apricots, bitter almonds, apples, peaches, cherries and plums, and in the roots of manioc.
Excerpted from Wikipedia’s “(R)-amygdalin” article, available under the CC BY-SA 4.0 licence.