21414-41-5 Usage
Description
Glucoraphanin is a glucosinolate found in broccoli, cauliflower, and mustard. Glucoraphanin is converted to sulforaphane by the enzyme myrosinase. In plants, sulforaphane deters insect predators and acts as a selective antibiotic. In humans, sulforaphane has been studied for its potential affects in neurodegenerative and cardiovascular diseases. Due to the potential health benefits, a variety of broccoli has been bred to contain two to three times more glucoraphanin than standard broccoli.
Discovery
In the early 1990’s, scientists at Johns Hopkins University (JHU) identified a compound derived from broccoli called glucoraphanin [2]. Glucoraphanin acts as part of the plant’s defense system. In fact, once converted to its bioactive form, sulforaphane, it is responsible for the characteristic sulfur smell/taste of broccoli. Glucoraphanin belongs to a category of compounds called glucosinolates, which are naturally found in cruciferous vegetables –with broccoli being the king of glucoraphanin. It is converted into sulforaphane by an enzyme found in broccoli called myrosinase or, if this enzyme is deactivated through the cooking process, the body's gut microflora will perform the conversion.
Glucoraphanin in broccoli
Glucoraphanin is a powerful and long-lasting antioxidant, found primarily in broccoli. However, the amount varies tremendously from one broccoli plant to another with no way for consumers to tell how much glucoraphanin is in the broccoli they buy. It has also been shown that this phytonutrient is present in much higher concentrations in the broccoli seeds and 3-day old broccoli sprouts. Brassica created TrueBroc? glucoraphanin from broccoli seeds in order to provide consumers with a concentrated source of glucoraphanin that contains consistent and meaningful levels. Glucoraphanin belongs to a category of compounds called glucosinolates which are naturally found in cruciferous vegetables. Glucosinolates are enzymatically converted into isothiocyanates, which are active in the body. This enzymatic conversion is performed by myrosinase, which is also found naturally in cruciferous vegetables.
Bioavailability studies indicate that glucoraphanin can be absorbed intact, but when eaten within broccoli it is primarily converted to sulforaphane during chewing, which is then absorbed in the upper intestine. Intact glucoraphanin can also be converted to sulforaphane by gut microflora (Holst & Williamson, 2004)
Definition
ChEBI: A thia-glucosinolic acid that is glucoerucin in which the sulfur atom of the methyl thioether group has been oxidised to the corresponding sulfoxide.
Check Digit Verification of cas no
The CAS Registry Mumber 21414-41-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,1,4,1 and 4 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 21414-41:
(7*2)+(6*1)+(5*4)+(4*1)+(3*4)+(2*4)+(1*1)=65
65 % 10 = 5
So 21414-41-5 is a valid CAS Registry Number.
InChI: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
21414-41-5Relevant articles and documents
Cytotoxic and antioxidant activity of 4-methylthio-3-butenyl isothiocyanate from Raphanus sativus L. (Kaiware Daikon) sprouts
Papi, Alessio,Orlandi, Marina,Bartolini, Giovanna,Barillari, Jessica,Iori, Renato,Paolini, Moreno,Ferroni, Fiammetta,Fumo, Maria Grazia,Pedulli, Gian Franco,Valgimigli, Luca
experimental part, p. 875 - 883 (2009/05/08)
There is high current interest in the chemopreventive potential of Brassica vegetables (cruciferae), particularly due to their content in glucosinolates (GL), which upon myrosinase hydrolysis release the corresponding isythiocyanates (ITC). Some ITCs, such as sulforaphane (SFN) from broccoli (Brassica oleacea italica), have been found to possess anticancer activity through induction of apoptosis in selected cell lines, as well as indirect antioxidant activity through induction of phase II detoxifying enzymes. Japanese daikon (Raphanus sativus L.) is possibly the vegetable with the highest per capita consumption within the Brassicaceae family. Thanks to a recently improved gram scale production process, it was possible to prepare sufficient amounts of the GL glucoraphasatin (GRH) as well as the corresponding ITC 4-methylthio-3-butenyl isothiocyanate (GRH-ITC) from its sprouts. This paper reports a study on the cytotoxic and apoptotic activities of GRH-ITC compared with the oxidized counterpart 4-methylsulfinyl-3-butenyl isothiocyanate (GRE-ITC) on three human colon carcinoma cell lines (LoVo, HCT-116, and HT-29) together with a detailed kinetic investigation of the direct antioxidant/radical scavenging ability of GRH and GRH-ITC. Both GRH-ITC and GRE-ITC reduced cell proliferation in a dose-dependent manner and induced apoptosis in the three cancer cell lines. The compounds significantly (p -1 s-1, respectively (at 298 K in methanol), whereas the corresponding value measured here for the reference antioxidant α-tocopherol was 425 ± 40 M-1 s-1. GRH reacted with H2O2 and tert-butyl hydroperoxide in water (pH 7.4) at 37°C, with rate constants of 1.9 ± 0.3 × 10-2 and 9.5 ± 0.3 × 10-4 M -1 s-1 (paralleling recently developed synthetic antioxidants) being quantitatively (>97%) converted to GRE. It is demonstrated that GRH-ITC has interesting antioxidant/radical scavenging properties, associated with a selective cytotoxic/apoptotic activity toward three human colon carcinoma cell lines, and very limited toxicity on normal human T-lymphocytes.
