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85440

Sigma-Aldrich

(−)-Sinigrin hydrate

≥99.0% (TLC)

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About This Item

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

biological source

plant (Brassica nigra)

Quality Level

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

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

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

InChI key

IUBVMJHASFBYGW-WBMBWNLZSA-M

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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

Signal Word

Warning

Hazard Statements

Hazard Classifications

Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A.J. MacLeod et al.
Phytochemistry, 25, 1047-1047 (1986)
Cong Cong et al.
International journal of molecular medicine, 48(2) (2021-07-20)
The present study investigated the function of sinigrin in angiotensin II (Ang II)‑induced renal damage. The results demonstrated that systolic blood pressure (SBP) and diastolic blood pressure (DBP) were increased in Ang II‑challenged rats, and sinigrin treatment inhibited their increase. The levels of blood
Richard A Lankau
Proceedings of the National Academy of Sciences of the United States of America, 109(28), 11240-11245 (2012-06-27)
Although reciprocal evolutionary responses between interacting species are a driving force behind the diversity of life, pairwise coevolution between plant competitors has received less attention than other species interactions and has been considered relatively less important in explaining ecological patterns.
Jóska Gerendás et al.
Journal of agricultural and food chemistry, 57(9), 3837-3844 (2009-03-25)
Food derived from Brassica species is rich in glucosinolates. Hydrolysis of these compounds by myrosinase yields isothiocyanates and other breakdown products, which due to their pungency represent the primary purpose of Indian mustard cultivation. Strong interactive effects of S (0.0
Derek Andersson et al.
Phytochemistry, 70(11-12), 1345-1354 (2009-08-26)
Myrosinases (EC 3.2.1.147) are beta-thioglucoside glucosidases present in Brassicaceae plants. These enzymes serve to protect plants against pathogens and insect pests by initiating breakdown of the secondary metabolites glucosinolates into toxic products. Several forms of myrosinases are present in plants

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