Structure via PubChem · Public domain (PubChem)
(R)-prunasin
Sign in to saveAlso known as (R)-alpha-(beta-D-glucopyranosyloxy)benzene-acetonitrile, (R)-(beta-D-glucopyranosyloxy)phenylacetonitrile, D-prunasin, prunasin
'(R)-prunasin' is a cyanogenic glycoside related to amygdalin. Chemically, it is the glucoside of (R)-mandelonitrile.
In the Vinony graph
Within Vinony's link graph, (R)-prunasin is referenced by 25 other articles, and connects out to Prunus amygdalus, International Standard Book Number and chemical compound.
It sits within the topics Chembox image size set, Cyanogenic glycosides and ECHA InfoCard ID from Wikidata.
Its subject is documented across 13 Wikipedia language editions.
Chemical data
- Formula
- C14H17NO6
- Molecular weight
- 295.29 g/mol
- IUPAC name
- (2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)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)O)O)O
- InChIKey
- ZKSZEJFBGODIJW-GMDXDWKASA-N
- XLogP
- -0.7
- Polar surface area
- 123 Ų
- H-bond donors
- 4
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
188 papers- Amygdalin, quackery or cure?Phytomedicine : international journal of phytotherapy and phytopharmacology · 2016
- Content and distribution of prunasin in Perilla frutescens.Journal of natural medicines · 2023
- β-Glucosidase activity in almond seeds.Plant physiology and biochemistry : PPB · 2018
- Facile Synthesis of Cyanogen Glycosides (R)-Prunasin, Linamarin and (S)-Heterodendrin.Bioscience, biotechnology, and biochemistry · 1998
- Bitterness in almonds.Plant physiology · 2008
via PubMed
Wikidata facts
- Subclass of
- carbohydrate
- Has part
- carbon
- Mass
- 295.105587
Show 6 more facts
- found in taxon
- Distimake tuberosus
- chemical formula
- C₁₄H₁₇NO₆
- canonical SMILES
- C1=CC=C(C=C1)C(C#N)OC2C(C(C(C(O2)CO)O)O)O
- isomeric SMILES
- C1=CC=C(C=C1)[C@H](C#N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
- subject has role
- enzyme inhibitor
- Commons category
- Prunasin
Sources (2)
via Wikidata · CC0
~6 min read
Encyclopedic overview
10 sectionsContents
- Natural occurrences
- Sambunigrin
- Biosynthesis
- Overview
- Biosynthesis of (''R'')-prunasin
- Biosynthesis of (''R'')-prunasin in ''Prunus dulcis''
- Biosynthesis of (''R'')-prunasin in ''Eucalyptus cladocalyx''
- Metabolic Pathway Interactions
- Toxicity
- References
{{Chembox | ImageFile = Prunasin.svg | ImageSize = 200px | ImageAlt = Chemical structure of prunasin | IUPACName = (R)-(β-D-Glucopyranosyloxy)(phenyl)acetonitrile | SystematicName = (R)-Phenyl{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile | OtherNames = (R)-PrunasinD-PrunasinD-Mandelonitrile-β-D-glucosidePrulaurasin LaurocerasinSambunigrin | Section1 = | Section2 = | Section3 = }}
'(R)-prunasin' is a cyanogenic glycoside related to amygdalin. Chemically, it is the glucoside of (R)-mandelonitrile.
Excerpted from Wikipedia’s “(R)-prunasin” article, available under the CC BY-SA 4.0 licence.