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Merck

85440

(−)-Sinigrin hydrate

≥99.0% (TLC)

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About This Item

Empirical Formula (Hill Notation):
C10H16KNO9S2 · xH2O
CAS Number:
3952-98-5
Molecular Weight:
397.46 (anhydrous basis)
NACRES:
NA.25
PubChem Substance ID:
57653046
UNSPSC Code:
12352201
MDL number:
MFCD00149447

Key Documents

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InChI

1S/C10H17NO9S2.K.H2O/c1-2-3-6(11-20-22(16,17)18)21-10-9(15)8(14)7(13)5(4-12)19-10;;/h2,5,7-10,12-15H,1,3-4H2,(H,16,17,18);;1H2/q;+1;/p-1/b11-6+;;/t5-,7-,8+,9-,10+;;/m1../s1

SMILES string

[K+].[H]O[H].OC[C@H]1O[C@@H](S\C(CC=C)=N\OS([O-])(=O)=O)[C@H](O)[C@@H](O)[C@@H]1O

InChI key

IUBVMJHASFBYGW-WBMBWNLZSA-M

biological source

plant (Brassica nigra)

assay

≥99.0% (TLC)

form

powder or crystals

optical activity

[α]20/D −17±1°, c = 1% in H2O

technique(s)

thin layer chromatography (TLC): suitable

color

white to faint beige

mp

128 (dec.) (lit.)

cation traces

K: 8.4-10.8

storage temp.

room temp

Quality Level

100

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Related Categories

Application

Sinigrin, a glucosinolate, is used as a systrate to identify, differentiate and characterize myrosinase(s)/thioglucoside glucohydrolase(s)/thioglucosidase(s). Sinigrin is used as a reference material in procedures for the isolation and identification of glucosinolates.

Biochem/physiol Actions

A β-D-thioglucopyranoside occurring in black mustard seeds and horseradish root. Substrate for thioglucosidase.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317

Hazard Classifications

Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

85440-VAR: + 85440-BULK: + 85440-1G: + 85440-100MG: + 85440-250MG:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG9090
BCCG2025
BCCF5121
BCCC2884
BCCC2885

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A.J. MacLeod et al.
Phytochemistry, 25, 1047-1047 (1986)
Vanessa Rungapamestry et al.
The British journal of nutrition, 99(4), 773-781 (2007-10-31)
Isothiocyanates have been implicated in the cancer-protective effects of brassica vegetables. When cabbage is consumed, sinigrin is hydrolysed by plant or microbial myrosinase partly to allyl isothiocyanate (AITC), which is mainly excreted as N-acetylcysteine conjugates (NAC) of AITC in urine.
Kari Jørgensen et al.
The Journal of experimental biology, 210(Pt 14), 2563-2573 (2007-07-03)
In nature, moths encounter nutritious and toxic substances in plants, and thus have to discriminate between a diversity of tastants. Whereas olfactory learning allowing memory of nutritious plants is well demonstrated, little is known about learning and memory of toxic
Richard A Lankau et al.
The American naturalist, 171(2), 150-161 (2008-01-17)
Plants interact with many different species throughout their life cycle. Recent work has shown that the ecological effects of multispecies interactions are often not predictable from studies of the component pairwise interactions. Little is known about how multispecies interactions affect
Kody A Belliveau et al.
Natural product research, 24(1), 24-33 (2009-12-17)
A simple procedure for extracting and purifying sinigrin from Oriental mustard (Brassica juncea) meal using cold water was developed. Subsequently, the chemical degradation of sinigrin due to enzymatic activity was monitored using (1)H NMR spectroscopy over the course of 30
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