21414-41-5

Basic information

• Product Name: GLUCORAPHANIN
• Synonyms: GLUCORAPHANIN;4-METHYLSULFINYLBUTYLGLUCOSINOLATE;1-Thio-β-D-glucopyranose 1-[N-(hydroxysulfonyloxy)-5-(methylsulfinyl)pentanimidate];1-Thio-β-D-glucopyranose 1-[N-(hydroxysulfonyloxy)-5-methylsulfinylpentanimidate];N-(Hydroxysulfonyloxy)-5-(methylsulfinyl)pentanimidothioic acid β-D-glucopyranosyl ester;GLUCORAPHANIN POTASSIUM SALT(RG);GLUCORAPHANIN POTASSIUM SALT(P);GLUCORAPHANIN POTASSIUM SALT(SH)
• CAS NO: 21414-41-5
• Molecular Formula: C₁₂H₂₃NO₁₀S₃
• Molecular Weight: 437.51
• Mol File: 21414-41-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.78±0.1 g/cm3 (20 ºC 760 Torr)
• Storage Temp.: 2-8°C
• PKA: -2.93±0.18(Predicted)
• CAS DataBase Reference: GLUCORAPHANIN(CAS DataBase Reference)
• NIST Chemistry Reference: GLUCORAPHANIN(21414-41-5)
• EPA Substance Registry System: GLUCORAPHANIN(21414-41-5)

Safety Data

• Hazardous Substances Data: 21414-41-5(Hazardous Substances Data)

Usage

Description

Glucoraphanin, a glucosinolate predominantly found in cruciferous vegetables such as broccoli, cauliflower, and mustard, is a bioactive compound that holds significant potential for human health. Upon enzymatic conversion by myrosinase, glucoraphanin is transformed into sulforaphane, a compound with demonstrated protective effects against various diseases. GLUCORAPHANIN also serves as a natural defense mechanism in plants, deterring insect predators and acting as a selective antibiotic. Recognizing its potential health benefits, a variety of broccoli has been specifically bred to contain higher concentrations of glucoraphanin.
Definition:
ChEBI defines glucoraphanin as a thia-glucosinolic acid, specifically glucoerucin, in which the sulfur atom of the methyl thioether group has been oxidized to the corresponding sulfoxide.

Uses

Used in the Food Industry:
Glucoraphanin is used as a functional ingredient in the food industry for its potential health-promoting properties. The increased levels of glucoraphanin in specially bred broccoli varieties contribute to the enhanced nutritional value of these vegetables, making them a popular choice for health-conscious consumers.
Used in the Pharmaceutical Industry:
Glucoraphanin is used as a precursor for the production of sulforaphane, which has been extensively studied for its potential effects on neurodegenerative and cardiovascular diseases. The compound's ability to modulate cellular pathways and exhibit protective effects against various disease conditions makes it a promising candidate for pharmaceutical applications.
Used in the Agricultural Industry:
Glucoraphanin serves as a natural insect repellent and selective antibiotic in plants, providing an environmentally friendly approach to pest control and disease management in agriculture. The breeding of broccoli with higher glucoraphanin content not only enhances its nutritional value but also contributes to more sustainable and effective agricultural practices.

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)

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

Upstream product

• 21973-56-8 4-methylsulthiobutyl glucosinolate 

Downstream Products

• 4478-93-7 D,L-sulforaphane 

Relevant articles and documents

Cytotoxic and antioxidant activity of 4-methylthio-3-butenyl isothiocyanate from Raphanus sativus L. (Kaiware Daikon) sprouts

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.