Glucoraphanin

Glucoraphanin is a glucosinolate found in broccoli,[1] cauliflower,[2] and mustard.[3]

Glucoraphanin

Potassium salt of glucoraphanin
Names
IUPAC name 1-S-[(1E)-5-(methylsulfinyl)-N-(sulfonatooxy)pentanimidoyl]-1-thio-β-D-glucopyranose
Other names Glucorafanin; 4-Methylsulfinylbutyl glucosinolate
Identifiers
CAS Number	21414-41-5 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:79311 Y
ChemSpider	570930
PubChem CID	656556
CompTox Dashboard (EPA)	DTXSID90894071
InChI InChI=1S/C12H23NO10S3/c1-25(18)5-3-2-4-8(13-23-26(19,20)21)24-12-11(17)10(16)9(15)7(6-14)22-12/h7,9-12,14-17H,2-6H2,1H3,(H,19,20,21)/p-1/t7-,9-,10+,11-,12+,25?/m1/s1 Key: GMMLNKINDDUDCF-SISVVIKZSA-M InChI=1/C12H23NO10S3/c1-25(18)5-3-2-4-8(13-23-26(19,20)21)24-12-11(17)10(16)9(15)7(6-14)22-12/h7,9-12,14-17H,2-6H2,1H3,(H,19,20,21)/p-1/t7-,9-,10+,11-,12+,25?/m1/s1 Key: GMMLNKINDDUDCF-XQSZSTCOBC
SMILES [O-]S(=O)(=O)ON=C(S[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)CCCCS(=O)C
Properties
Chemical formula	C12H23NO10S3
Molar mass	437.49 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

Glucoraphanin is converted to sulforaphane by the enzyme myrosinase[4]. In plants, sulforaphane deters insect predators and acts as a selective antibiotic.[5] In humans, sulforaphane has been studied for its potential effects in neurodegenerative[6] and cardiovascular diseases.[7]

Due to the potential health benefits, a variety of broccoli has been bred to contain two to three times more glucoraphanin than standard broccoli.[8]

Romanesco broccoli has been found to contain ten times more glucoraphanin than typical broccoli varieties.[9] Frostara, Black Tuscany and red cabbage also contain much higher levels of glucoraphanin than broccoli.[9]