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.
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.