28463-24-3

Basic information

• Product Name: Glucoraphenin
• Synonyms: Glucoraphenin;glucoraphenin(1-)
• CAS NO: 28463-24-3
• Molecular Formula: C₁₂H₂₁NO₁₀S₃
• Molecular Weight: 435.493
• Mol File: 28463-24-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• Refractive Index: 1.682
• PKA: -3.03±0.18(Predicted)
• CAS DataBase Reference: Glucoraphenin(CAS DataBase Reference)
• NIST Chemistry Reference: Glucoraphenin(28463-24-3)
• EPA Substance Registry System: Glucoraphenin(28463-24-3)

Safety Data

• Hazardous Substances Data: 28463-24-3(Hazardous Substances Data)

Usage

Description

Glucoraphenin, also known as sulforaphane glucosinolate, is a natural compound found in cruciferous vegetables such as broccoli, Brussels sprouts, and cauliflower. It is converted into sulforaphane by the enzyme myrosinase when the vegetable is chewed or chopped. Sulforaphane possesses anti-cancer, anti-inflammatory, and antioxidant properties and has been studied for its potential role in preventing certain types of cancer, as well as for its positive effects on heart health and detoxification.

Uses

Used in Cancer Prevention:
Glucoraphenin is used as a cancer-preventive agent for its conversion into sulforaphane, which has been studied for its potential role in preventing certain types of cancer, such as breast, prostate, and bladder cancer.
Used in Anti-Inflammatory Applications:
Glucoraphenin is used as an anti-inflammatory agent due to the anti-inflammatory properties of sulforaphane, which is produced from glucoraphenin.
Used in Antioxidant Applications:
Glucoraphenin is used as an antioxidant agent because of the antioxidant properties of sulforaphane, which is derived from glucoraphenin.
Used in Heart Health:
Glucoraphenin is used to promote heart health due to the positive effects of sulforaphane on heart health, which is produced when glucoraphenin is converted by myrosinase.
Used in Detoxification:
Glucoraphenin is used for detoxification purposes because of the detoxification properties of sulforaphane, which is generated from glucoraphenin.

InChI:InChI=1/C12H21NO11S3/c1-26(19)4-2-3-6(11(18)13-24-27(20,21)22)12(25)10(17)9(16)8(15)7(5-14)23-12/h2,4,6-10,14-17,25H,3,5H2,1H3,(H,13,18)(H,20,21,22)/b4-2+/t6?,7-,8-,9+,10-,12+,26?/m1/s1

Upstream product

• 28463-23-2 glucoraphasatin 

Downstream Products

• 592-95-0 4-methylsulfinyl-3-butenyl isothiocyanate 

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.