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SMB00173

Sigma-Aldrich

Prunasin

≥90% (LC/MS-ELSD)

Synonym(s):

D-Mandelonitrile β-D-glucoside

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About This Item

Empirical Formula (Hill Notation):
C14H17NO6
CAS Number:
99-18-3
Molecular Weight:
295.29
EC Number:
202-738-0
MDL number:
MFCD00049232
UNSPSC Code:
12352205
PubChem Substance ID:
329824839
NACRES:
NA.25

Assay

≥90% (LC/MS-ELSD)

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

OCC1OC(OC(C#N)c2ccccc2)C(O)C(O)C1O

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

InChI key

ZKSZEJFBGODIJW-UHFFFAOYSA-N

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General description

Natural product derived from plant source.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H360

Precautionary Statements

P201 - P301 + P310 + P330

Hazard Classifications

Acute Tox. 3 Oral - Repr. 1B

Storage Class Code

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

Certificates of Analysis (COA)

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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
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
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
V Berenguer-Navarro et al.
Journal of agricultural and food chemistry, 50(24), 6960-6963 (2002-11-14)
The determination of cyanogenic compounds in plants is often performed by HPLC. However, in this analysis, interferences due to compounds in the matrix, such as tannins and other pigments, are encountered, especially in roots and leaves. A new method is
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