SMB00173
Prunasin
Synonym(s):
D-Mandelonitrile β-D-glucoside
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About This Item
Empirical Formula (Hill Notation):
C14H17NO6
CAS Number:
Molecular Weight:
295.29
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
12352205
EC Number:
202-738-0
MDL number:
InChI key
ZKSZEJFBGODIJW-UHFFFAOYSA-N
InChI
1S/C14H17NO6/c15-6-9(8-4-2-1-3-5-8)20-14-13(19)12(18)11(17)10(7-16)21-14/h1-5,9-14,16-19H,7H2
SMILES string
OCC1OC(OC(C#N)c2ccccc2)C(O)C(O)C1O
Quality Level
form
solid
application(s)
metabolomics
vitamins, nutraceuticals, and natural products
Related Categories
General description
Natural product derived from plant source.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 3 Oral - Repr. 1B
Storage Class
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Jandirk Sendker et al.
Phytochemistry, 70(3), 388-393 (2009-02-07)
The cyanogenic glucoside-related compound prunasinamide, (2R)-beta-d-glucopyranosyloxyacetamide, has been detected in dried, but not in fresh leaves of the prunasin-containing species Olinia ventosa, Prunus laurocerasus, Pteridium aquilinium and Holocalyx balansae. Experiments with leaves of O. ventosa indicated a connection between amide
Y Mizushina et al.
Journal of biochemistry, 126(2), 430-436 (1999-07-29)
A DNA polymerase beta (pol. beta) inhibitor has been isolated independently from two organisms; a red perilla, Perilla frutescens, and a mugwort, Artemisia vulgaris. These molecules were determined by spectroscopic analyses to be the cyanogenic glucoside, D-mandelonitrile-beta-D-glucoside, prunasin. The compound
J Christensen et al.
Organic letters, 3(14), 2193-2195 (2001-07-07)
[structure: see text] Leaves of the edible passion fruit plant, Passiflora edulis, contain benzylic beta-D-allopyranosides 1 and 2, representatives of a rare class of natural glycosides with D-allose as the only sugar constituent. The glycoside 1 is the first known
Roslyn M Gleadow et al.
Phytochemistry, 63(6), 699-704 (2003-07-05)
Cyanogenesis (i.e. the evolution of HCN from damaged plant tissue) requires the presence of two biochemical pathways, one controlling synthesis of the cyanogenic glycoside and the other controlling the production of a specific degradative beta-glucosidase. The sole cyanogenic glycoside in
Rebecca E Miller et al.
Phytochemistry, 67(1), 43-51 (2005-11-26)
The cyanogenic diglycoside lucumin ((R)-mandelonitrile-beta-D-primeveroside) and monoglucoside prunasin ((R)-mandelonitrile-beta-D-glucoside) were isolated from the foliage of the rare Australian rainforest tree species Clerodendrum grayi (Lamiaceae). This is the first reported isolation of the diglycoside lucumin from vegetative tissue (foliage), and the
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