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Sinigrin information


Sinigrin
Names
IUPAC name
(Z)-N-[1-(β-D-glucopyranosylsulfanyl)but-3-en-1-ylidene]hydroxylamine-O-sulfonic acid
Systematic IUPAC name
(Z)-N-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}but-3-en-1-ylidene)hydroxylamine-O-sulfonic acid
Other names
Allyl glucosinolate; 2-Propenyl glucosinolate; (1Z)-N-(Sulfooxy)but-3-enimidoyl 1-thio-β-D-glucopyranoside
Identifiers
CAS Number
  • Sinigrin: 534-69-0 checkY
  • K+ salt: 3952-98-5 checkY
3D model (JSmol)
  • Sinigrin: Interactive image
  • K+ salt: Interactive image
ChEBI
  • Sinigrin: CHEBI:79317 checkY
ChemSpider
  • Sinigrin: 4588961 checkY
  • K+ salt: 4576678 checkY
PubChem CID
  • Sinigrin: 5486549
  • K+ salt: 23684362
UNII
  • K+ salt: 50UM64RMBJ
InChI
  • InChI=1S/C10H17NO9S2/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)/b11-6-/t5-,7-,8+,9-,10+/m1/s1 checkY
    Key: PHZOWSSBXJXFOR-GLVDENFASA-N checkY
  • K+ salt: InChI=1S/C10H17NO9S2.K/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);/q;+1/p-1/b11-6-;/t5-,7-,8+,9-,10+;/m1./s1
    Key: QKFAFSGJTMHRRY-FVDOMRANSA-M
SMILES
  • Sinigrin: C=CC/C(=N/OS(=O)(=O)O)/S[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
  • K+ salt: C=CC/C(=N/OS(=O)(=O)[O-])/S[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O.[K+]
Properties
Chemical formula
C10H17NO9S2
Molar mass 359.36 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Sinigrin or allyl glucosinolate is a glucosinolate that belongs to the family of glucosides found in some plants of the family Brassicaceae such as Brussels sprouts, broccoli, and the seeds of black mustard (Brassica nigra). Whenever sinigrin-containing plant tissue is crushed or otherwise damaged, the enzyme myrosinase degrades sinigrin to a mustard oil (allyl isothiocyanate), which is responsible for the pungent taste of mustard and horseradish.[1] Seeds of white mustard, Sinapis alba, give a less pungent mustard because this species contains a different glucosinolate, sinalbin.

  1. ^ Richard, H. "Arômes alimentaires" (PDF) (in French). Archived from the original (PDF) on 2007-02-14.

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Sinigrin

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Sinigrin or allyl glucosinolate is a glucosinolate that belongs to the family of glucosides found in some plants of the family Brassicaceae such as Brussels...

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Glucosinolate

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glucosinolates and their isothiocyanate products: Allylglucosinolate (sinigrin) is the precursor of allyl isothiocyanate Benzylglucosinolate (glucotropaeolin)...

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Brussels sprout

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van Doorn identified the chemicals that make Brussels sprouts bitter: sinigrin and progoitrin. This enabled Dutch seed companies to cross-breed archived...

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Mustard oil

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chemical reaction between the enzyme myrosinase and a glucosinolate known as sinigrin from the seeds of black mustard (Brassica nigra) or brown Indian mustard...

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Horseradish

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aroma. When cut or grated, enzymes from within the plant cells digest sinigrin (a glucosinolate) to produce allyl isothiocyanate (mustard oil), which...

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Wasabi

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including those resulting from the hydrolysis of thioglucosides, including sinigrin and other glucosinolates, into glucose and methylthioalkyl isothiocyanates:...

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Allyl isothiocyanate

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the enzyme myrosinase is released and acts on a glucosinolate known as sinigrin to give allyl isothiocyanate. This serves the plant as a defense against...

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Glucoside

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taste; their principal occurrence is in mustard and Tropaeolum seeds. Sinigrin, or the potassium salt of inyronic acid not only occurs in mustard seed...

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Brassicaceae

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Glucocapparin Glucoraphanin Gluconasturtiin Glucotropaeolin Progoitrin Sinigrin Sinalbin Isothiocyanates (ITC, mustard oils) Sulforaphane (SFN) Raphanin...

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Glycoside

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contains the prefix thio-, these compounds contain sulfur. Examples include sinigrin, found in black mustard, and sinalbin, found in white mustard. Carbohydrate...

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Rhamphospermum arvense

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I.E.; Morra, M.J. (5 November 2014). "Simultaneous quantification of sinigrin, sinalbin, and anionic glucosinolate hydrolysis products in Brassica juncea...

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Isothiocyanate

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enzyme myrosinase, which acts on glucosinolates to release isothiocyanates. Sinigrin is the precursor to allyl isothiocyanate Glucotropaeolin is the precursor...

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Capsaicin

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Terpenoids Phenolic compounds Glucosinolates Precursor to isothiocyanates Sinigrin Gluconasturtiin Glucoraphanin Aglycone derivatives Isothiocyanates Sulforaphane...

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Dietary fiber

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Terpenoids Phenolic compounds Glucosinolates Precursor to isothiocyanates Sinigrin Gluconasturtiin Glucoraphanin Aglycone derivatives Isothiocyanates Sulforaphane...

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Pieris oleracea

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plant contains the oviposition stimulant sinigrin. Females of this species react very strongly to sinigrin, especially when compared to similar species...

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Polyphenol

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Terpenoids Phenolic compounds Glucosinolates Precursor to isothiocyanates Sinigrin Gluconasturtiin Glucoraphanin Aglycone derivatives Isothiocyanates Sulforaphane...

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Sinalbin

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contrast to mustard from black mustard (Brassica nigra) seeds which contain sinigrin, mustard from white mustard seeds has only a weakly pungent taste. Sinalbin...

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Allelopathy

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temperate forests may be partly due to its excretion of glucosinolates like sinigrin that can interfere with mutualisms between native tree roots and their...

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List of phytochemicals in food

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Alkylresorcinols wholegrain wheat, rye and barley. Piperine black pepper. Sinigrin (the precursor to allyl isothiocyanate) broccoli family, brussels sprouts...

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Saponin

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Terpenoids Phenolic compounds Glucosinolates Precursor to isothiocyanates Sinigrin Gluconasturtiin Glucoraphanin Aglycone derivatives Isothiocyanates Sulforaphane...

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Betalain

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Terpenoids Phenolic compounds Glucosinolates Precursor to isothiocyanates Sinigrin Gluconasturtiin Glucoraphanin Aglycone derivatives Isothiocyanates Sulforaphane...

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Phytochemical

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Terpenoids Phenolic compounds Glucosinolates Precursor to isothiocyanates Sinigrin Gluconasturtiin Glucoraphanin Aglycone derivatives Isothiocyanates Sulforaphane...

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Gluconasturtiin

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vegetables, it is also found in horseradish (Armoracia rusticana) along with sinigrin. Both compounds elicit a pungent taste. The compound was first reported...

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Glucoraphanin

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April 2017. Retrieved 26 June 2022. Oh, K.; SangOk, K.; Rak, C. (2015). "Sinigrin content of different parts of Dolsan leaf mustard". Korean Journal of Food...

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Myrosinase

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280 μmol/min per mg of protein on the substrate, allyl glucosinolate (sinigrin) when in the presence of 500 μM ascorbate. Sulfate, a byproduct of glucosinolate...

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Naturally occurring phenols

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Terpenoids Phenolic compounds Glucosinolates Precursor to isothiocyanates Sinigrin Gluconasturtiin Glucoraphanin Aglycone derivatives Isothiocyanates Sulforaphane...

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Brevicoryne brassicae

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thoracic muscles; the aphids also uptake glucosinolates, particularly sinigrin, from the plants on which they feed, storing the glucosinolates in their...

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Phytosterol

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Terpenoids Phenolic compounds Glucosinolates Precursor to isothiocyanates Sinigrin Gluconasturtiin Glucoraphanin Aglycone derivatives Isothiocyanates Sulforaphane...

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Allyl cyanide

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Food Chem. Vol. 25, No. 6, (1997), 1234-1238 C. Krul et al. Metabolism of sinigrin (2-propenyl glucosinolate) by the human colonic microflora in a dynamic...

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