Glucoraphanin information

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, Sulforaphane glucosinolate
Identifiers
CAS Number	21414-41-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:79311 ;
ChemSpider	570930;
PubChem CID	656556;
UNII	Q86A197713 ;
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 a glucosinolate found in broccoli,^[1]^[2] mustard and other cruciferous vegetables.^[3]^[4]

Glucoraphanin is converted to sulforaphane by the enzyme myrosinase.^[5] In plants, sulforaphane deters insect predators and acts as a selective antibiotic.^[6]

^ James, D.; Devaraj, S.; Bellur, P.; Lakkanna, S.; Vicini, J.; Boddupalli, S. (2012). "Novel concepts of broccoli sulforaphanes and disease: Induction of phase II antioxidant and detoxification enzymes by enhanced-glucoraphanin broccoli". Nutrition Reviews. 70 (11): 654–65. doi:10.1111/j.1753-4887.2012.00532.x. PMID 23110644.
^ Jeffery, E. H.; Brown, A. F.; Kurilich, A. C.; Keck, A. S.; Matusheski, N.; Klein, B. P.; Juvik, J. A. (2003). "Variation in content of bioactive components in broccoli". Journal of Food Composition and Analysis. 16 (3): 323–330. doi:10.1016/S0889-1575(03)00045-0.
^ Cite error: The named reference lpi was invoked but never defined (see the help page).
^ Oh, K.; SangOk, K.; Rak, C. (2015). "Sinigrin content of different parts of Dolsan leaf mustard". Korean Journal of Food Preservation. 22 (4): 553–558. doi:10.11002/kjfp.2015.22.4.553.
^ Cuomo, Valentina; Luciano, Fernando B.; Meca, Giuseppe; Ritieni, Alberto; Mañes, Jordi (26 November 2014). "Bioaccessibility of glucoraphanin from broccoli using an gastrointestinal digestion model". CyTA - Journal of Food. 13 (3): 361–365. doi:10.1080/19476337.2014.984337. S2CID 96578211.
^ Fahey, Jed W.; Holtzclaw, W. David; Wehage, Scott L.; Wade, Kristina L.; Stephenson, Katherine K.; Talalay, Paul; Mukhopadhyay, Partha (2 November 2015). "Sulforaphane Bioavailability from Glucoraphanin-Rich Broccoli: Control by Active Endogenous Myrosinase". PLOS ONE. 10 (11): e0140963. Bibcode:2015PLoSO..1040963F. doi:10.1371/journal.pone.0140963. PMC 4629881. PMID 26524341.

[1] James, D.; Devaraj, S.; Bellur, P.; Lakkanna, S.; Vicini, J.; Boddupalli, S. (2012). "Novel concepts of broccoli sulforaphanes and disease: Induction of phase II antioxidant and detoxification enzymes by enhanced-glucoraphanin broccoli". Nutrition Reviews. 70 (11): 654–65. doi:10.1111/j.1753-4887.2012.00532.x. PMID 23110644.

[2] Jeffery, E. H.; Brown, A. F.; Kurilich, A. C.; Keck, A. S.; Matusheski, N.; Klein, B. P.; Juvik, J. A. (2003). "Variation in content of bioactive components in broccoli". Journal of Food Composition and Analysis. 16 (3): 323–330. doi:10.1016/S0889-1575(03)00045-0.

[lpi-3] Cite error: The named reference lpi was invoked but never defined (see the help page).

[4] Oh, K.; SangOk, K.; Rak, C. (2015). "Sinigrin content of different parts of Dolsan leaf mustard". Korean Journal of Food Preservation. 22 (4): 553–558. doi:10.11002/kjfp.2015.22.4.553.

[5] Cuomo, Valentina; Luciano, Fernando B.; Meca, Giuseppe; Ritieni, Alberto; Mañes, Jordi (26 November 2014). "Bioaccessibility of glucoraphanin from broccoli using an gastrointestinal digestion model". CyTA - Journal of Food. 13 (3): 361–365. doi:10.1080/19476337.2014.984337. S2CID 96578211.

[6] Fahey, Jed W.; Holtzclaw, W. David; Wehage, Scott L.; Wade, Kristina L.; Stephenson, Katherine K.; Talalay, Paul; Mukhopadhyay, Partha (2 November 2015). "Sulforaphane Bioavailability from Glucoraphanin-Rich Broccoli: Control by Active Endogenous Myrosinase". PLOS ONE. 10 (11): e0140963. Bibcode:2015PLoSO..1040963F. doi:10.1371/journal.pone.0140963. PMC 4629881. PMID 26524341.

Glucoraphanin information

and 24 Related for: Glucoraphanin information

Glucoraphanin

Sulforaphane

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Broccoli

Kale

Dietary fiber

Glucosinolate

Brassicaceae

Isothiocyanate

Capsaicin

Monsanto

Black radish

Secondary metabolite

List of phytochemicals in food

Polyphenol

Phytochemical

Saponin

Betalain

Phytosterol

Naturally occurring phenols

Arame

Brassica rupestris

Phytosteroid

Erucin

Names
Potassium salt of glucoraphanin
IUPAC name 1-S-[(1E)-5-(methylsulfinyl)-N-(sulfonatooxy)pentanimidoyl]-1-thio-β-D-glucopyranose
Other names Glucorafanin; 4-Methylsulfinylbutyl glucosinolate, Sulforaphane glucosinolate
Identifiers
CAS Number	21414-41-5^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:79311^Y
ChemSpider	570930
PubChem CID	656556
UNII	Q86A197713^Y
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