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  • Purity: 99%
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Keywords

DL-Sulforaphane 4478-93-7 DL-Sulforaphane

Quick Details

  • Appearance:white powder
  • Application:chemicals industry
  • PackAge:25KG/Drum
  • ProductionCapacity:5|Metric Ton|Month
  • Storage:2-8°C
  • Transportation:By air /Sea/ coruier

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DL-Sulforaphane Basic information
Product Name: DL-Sulforaphane
Synonyms: sulforafan;sulforaphan;DL-Sulforaphane 4478-93-7;Sulforaphane Racemate;D,L-Sulforaphane - CAS 4478-93-7 - Calbiochem;sulforaphane;R-SULFORAPHANE;R,S-SULFORAPHANE
CAS: 4478-93-7
MF: C6H11NOS2
MW: 177.29
EINECS: 200-001-8
Product Categories: Aliphatics;Antitumour;Sulphur Derivatives;Miscellaneous Natural Products;All Inhibitors;Inhibitors;Sulfur & Selenium Compounds
Mol File: 4478-93-7.mol
DL-Sulforaphane Structure
 
DL-Sulforaphane Chemical Properties
Boiling point  125-135°C
density  1.17±0.1 g/cm3(Predicted)
storage temp.  -20°C
solubility  DMSO: 40 mg/mL, soluble
form  liquid
color  slightly yellow
Stability: Light Sensitive
CAS DataBase Reference 4478-93-7(CAS DataBase Reference)
 
Safety Information
Safety Statements  23-24/25
WGK Germany  3
HS Code  29309090
MSDS Information
Provider Language
SigmaAldrich English
 
DL-Sulforaphane Usage And Synthesis
Description Sulforaphane(SFN)(1-isothiocyanato-4-methylsulfinylbutane) is a compound within the isothiocyanate group of organosulfur compounds and mainly found in cruciferous vegetables. It is produced when the enzyme myrosinase transforms glucoraphanin,a prodrug or storage form of SFN,into SFN upon damage to the plant (such as from chewing),which allows the two compounds to mix and react. Glucoraphanin is one of a few molecules known as isothiocyanates,existing alongside Sinigrin (metabolized into allylisothiocyanate).SFN promotes detoxification,prevents and combats cancer,lowers cholesterol,improves diabetes,can boost the immune system, is antiviral, antibacterial, and antifungal, combats inflammation,protect skin,eyes,kidneys, and brain, and restores its cognitive function. Deep insight in several studies has reported that dietary intake of cruciferous vegetables has a direct association in the decline in the incidence of various tumors such as prostate,cervical,ovarian,and lung cancer. It improves the liver function,attenuates pain,improves hair growth,promotes bone formation, and prevents muscle damage.SFN treatment reducesDNA damage and mutation rate when cancer-causing chemicals bind DNA.Although an ideal dosage is not known, the dietary addition of 0.1-0.5mg/kg SFN to rats has been noted to be bioactive. This is an estimated human dose of 7-34mg for a 1501b person; 9-45mg for a 2001b person; 11-57mg for a 250lb person.
Chemical Properties SFN[Sulforaphane;DL-Sulforaphane] in liquid form is slightly yellow in color,with a molecular weight about 177.28g/mol. SFN has an average melting point of 74.6℃,although it may range between 58.6°C and 91.2°C and its molecular formula is C6H11NOS2. It is soluble in DMSO, methanol, or water-like solvents.
SFN exists in food in its food-bound form known as Glucoraphanin. It is present in a wide range of vegetables such as cabbage, cauliflower, bok choy, kale, chinese broccoli, mustard, turnip, radish, and watercress.
Uses

LNCaP prostate cancer cells were treated with DL-Sulforaphane to study the effect on androgen receptor. Effects on malathion toxicity was studied in rats by treating them with DL-Sulforaphane.

Uses Potent, selective inducer of phase II detoxification enzymes with anticarcinogenic properties. Occurs naturally in broccoli. It was found to inhibit chemically induced mammary tumor formation in rats. Antitumor agent
LNCaP prostate cancer cells were treated with DL-Sulforaphane to study the effect on androgen receptor. Effects on malathion toxicity was studied in rats by treating them with DL-Sulforaphane.
Nrf2 activation of the antioxidant response element (ARE) is central to cytoprotective gene expression against oxidative and/or electrophilic stress.
Unless activated by inflammatory, environmental, or oxidative stressors, Nrf2 is sequestered in the cytoplasm by its repressor, Keap1.
Because of its protective capabilities, small molecules that activate Nrf2 signaling are being examined as potential anti-cancer or anti-inflammatory agents.
Sulforaphane is an isothiocyanate derived from cruciferous vegetables, including broccoli, that potently induces chemopreventative enzymes via Keap1-Nrf2 signaling and ARE-driven gene expression.
At 15 μM, sulforaphane inhibits class I and II HDAC activity and suppresses tumor growth by inducing cell cycle arrest and apoptosis selectively in various cancerous prostate epithelial cells without affecting normal cells.
Differential effects of sulforaphane on histone deacetylases, cell cycle arrest and apoptosis in normal prostate cells versus hyperplastic and cancerous prostate cells
Definition ChEBI: An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.
General Description

An isothiocyanate isolated from broccoli that acts as a potent inducer of phase II detoxifying enzymes in mouse tissues and murine hepatoma cells in culture. It has been shown to be an effective agent in prevention of chemically-induced mammary tumors in rats. It also inhibits the phase I cytochrome P450 isoenzymes 2E1 and IA2 which have been associated with the activation of carcinogens. The induction of phase II enzymes is mediated by mitogen-activated protein kinase (MAPK) pathway.

Biological Activity Selective inducer of phase II detoxification enzymes with anticarcinogenic properties. Organosulfur compound found in cruciferous vegetables, including broccoli.
Sulforaphane is an anti-cancer, anti-microbial and anti-diabetic compound found in cruciferous vegetables. It induces the production of detoxifying enzymes such as quinone reductase and glutathione S-transferase that cause xenobiotic transformation. Sulforaphane also increases the transcription of tumor suppressor proteins and inhibits histone deacetylases. It modulates inflammatory responses by suppressing the LPS-mediated expression of iNOS, COX-2, IL-1β and TNF-α.
Biochem/physiol Actions Selective inducer of phase II detoxification enzymes with anticarcinogenic properties. Organosulfur compound found in cruciferous vegetables, including broccoli.
Anticancer Research It is an isothiocyanate compound found in cruciferous vegetables like broccoli,Brussels sprouts, and cabbages. It induces phase II drug metabolism enzymes ofxenobiotic transformation and enhances the transcription of tumor suppressionproteins. It promotes cytotoxicity in p53-deleted colon cancer cells by mitochondriaandlysosome-dependent cell death. Due to the effect of sulforaphane, Bax is alsobeing increased in the presence of inhibition of JNK-induced Bcl-2 followed bymitochondrial cytochrome-C release and activation of apoptosis. Self-renewal Wnt/β-catenin signaling pathway is downregulated by sulforaphane in breast cancer stemcells. It has been reported to inhibit the activity of histone deacetylase (HDAC) andto reduce the number of polyps in Apcmin/+ mouse by inhibiting AKT and ERKsignaling and protein expression of COX-2 and cyclin-D1. Sulforaphane alsoinhibits the growth of SW620 cells by inducing apoptosis (Clarke et al. 2008). Inhuman colon cancer cells (HT-29), sulforaphane showed increased dose-dependentluciferase activity of AP-1, induced JAK activity, and inhibited NF-κB luciferaseactivation induced by LPS. It is also reported to inhibit cellular proliferation and toinduce apoptosis. In HepG2 human hepatoma cells, sulforaphane significantlyinduces the expression of the Nrf-2 protein and activation of ARE-mediatedtranscription, delays Nrf-2 degradation by inhibition of Keap1, and activates theexpression of transcription of the antioxidant HO-1 enzyme. This activation of thetranscription is partially modulated by the signaling pathway of p38 MAPK, whilep38 MAPK phosphorylates Nrf-2 and improves the binding between the proteinsNrf-2 and Keap1. In the PC-3 cells of human prostate cancer, sulforaphanesuppresses the expression regulated by NF-κB and NF-κB signaling pathway by theIκBα and IKK pathways (Wang et al. 2012).
Sulforaphane strongly inhibits the expression of TNFα, IL-1β, COX-2, and iNOSand the expression of mRNA stimulated by LPS in the primary peritonealmacrophages of wild-type mouse. The expression of HO-1 is also increasedsignificantly. The anti-inflammatory effects have been mitigated in the primaryperitoneal macrophages of Nrf2 ( / ), and therefore the anti-inflammatory activityis mainly exerted by the Nrf2 pathway in mouse peritoneal macrophages.Sulforaphane induces detoxification enzymes metabolizing drugs via phase I(modification), phase II (conjugation), and phase III (further modification andexcretion) and also increases the expression of genes that detoxify directly theexogenous carcinogenic toxins, endogenous ROS, and the genes which can recognizeand repair damaged proteins (Wang et al. 2012).
 
DL-Sulforaphane Preparation Products And Raw materials

 

Details:

 

DL-Sulforaphane Basic information
Product Name: DL-Sulforaphane
Synonyms: sulforafan;sulforaphan;DL-Sulforaphane 4478-93-7;Sulforaphane Racemate;D,L-Sulforaphane - CAS 4478-93-7 - Calbiochem;sulforaphane;R-SULFORAPHANE;R,S-SULFORAPHANE
CAS: 4478-93-7
MF: C6H11NOS2
MW: 177.29
EINECS: 200-001-8
Product Categories: Aliphatics;Antitumour;Sulphur Derivatives;Miscellaneous Natural Products;All Inhibitors;Inhibitors;Sulfur & Selenium Compounds
Mol File: 4478-93-7.mol
DL-Sulforaphane Structure
 
DL-Sulforaphane Chemical Properties
Boiling point  125-135°C
density  1.17±0.1 g/cm3(Predicted)
storage temp.  -20°C
solubility  DMSO: 40 mg/mL, soluble
form  liquid
color  slightly yellow
Stability: Light Sensitive
CAS DataBase Reference 4478-93-7(CAS DataBase Reference)
 
Safety Information
Safety Statements  23-24/25
WGK Germany  3
HS Code  29309090
MSDS Information
Provider Language
SigmaAldrich English
 
DL-Sulforaphane Usage And Synthesis
Description Sulforaphane(SFN)(1-isothiocyanato-4-methylsulfinylbutane) is a compound within the isothiocyanate group of organosulfur compounds and mainly found in cruciferous vegetables. It is produced when the enzyme myrosinase transforms glucoraphanin,a prodrug or storage form of SFN,into SFN upon damage to the plant (such as from chewing),which allows the two compounds to mix and react. Glucoraphanin is one of a few molecules known as isothiocyanates,existing alongside Sinigrin (metabolized into allylisothiocyanate).SFN promotes detoxification,prevents and combats cancer,lowers cholesterol,improves diabetes,can boost the immune system, is antiviral, antibacterial, and antifungal, combats inflammation,protect skin,eyes,kidneys, and brain, and restores its cognitive function. Deep insight in several studies has reported that dietary intake of cruciferous vegetables has a direct association in the decline in the incidence of various tumors such as prostate,cervical,ovarian,and lung cancer. It improves the liver function,attenuates pain,improves hair growth,promotes bone formation, and prevents muscle damage.SFN treatment reducesDNA damage and mutation rate when cancer-causing chemicals bind DNA.Although an ideal dosage is not known, the dietary addition of 0.1-0.5mg/kg SFN to rats has been noted to be bioactive. This is an estimated human dose of 7-34mg for a 1501b person; 9-45mg for a 2001b person; 11-57mg for a 250lb person.
Chemical Properties SFN[Sulforaphane;DL-Sulforaphane] in liquid form is slightly yellow in color,with a molecular weight about 177.28g/mol. SFN has an average melting point of 74.6℃,although it may range between 58.6°C and 91.2°C and its molecular formula is C6H11NOS2. It is soluble in DMSO, methanol, or water-like solvents.
SFN exists in food in its food-bound form known as Glucoraphanin. It is present in a wide range of vegetables such as cabbage, cauliflower, bok choy, kale, chinese broccoli, mustard, turnip, radish, and watercress.
Uses

LNCaP prostate cancer cells were treated with DL-Sulforaphane to study the effect on androgen receptor. Effects on malathion toxicity was studied in rats by treating them with DL-Sulforaphane.

Uses Potent, selective inducer of phase II detoxification enzymes with anticarcinogenic properties. Occurs naturally in broccoli. It was found to inhibit chemically induced mammary tumor formation in rats. Antitumor agent
LNCaP prostate cancer cells were treated with DL-Sulforaphane to study the effect on androgen receptor. Effects on malathion toxicity was studied in rats by treating them with DL-Sulforaphane.
Nrf2 activation of the antioxidant response element (ARE) is central to cytoprotective gene expression against oxidative and/or electrophilic stress.
Unless activated by inflammatory, environmental, or oxidative stressors, Nrf2 is sequestered in the cytoplasm by its repressor, Keap1.
Because of its protective capabilities, small molecules that activate Nrf2 signaling are being examined as potential anti-cancer or anti-inflammatory agents.
Sulforaphane is an isothiocyanate derived from cruciferous vegetables, including broccoli, that potently induces chemopreventative enzymes via Keap1-Nrf2 signaling and ARE-driven gene expression.
At 15 μM, sulforaphane inhibits class I and II HDAC activity and suppresses tumor growth by inducing cell cycle arrest and apoptosis selectively in various cancerous prostate epithelial cells without affecting normal cells.
Differential effects of sulforaphane on histone deacetylases, cell cycle arrest and apoptosis in normal prostate cells versus hyperplastic and cancerous prostate cells
Definition ChEBI: An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.
General Description

An isothiocyanate isolated from broccoli that acts as a potent inducer of phase II detoxifying enzymes in mouse tissues and murine hepatoma cells in culture. It has been shown to be an effective agent in prevention of chemically-induced mammary tumors in rats. It also inhibits the phase I cytochrome P450 isoenzymes 2E1 and IA2 which have been associated with the activation of carcinogens. The induction of phase II enzymes is mediated by mitogen-activated protein kinase (MAPK) pathway.

Biological Activity Selective inducer of phase II detoxification enzymes with anticarcinogenic properties. Organosulfur compound found in cruciferous vegetables, including broccoli.
Sulforaphane is an anti-cancer, anti-microbial and anti-diabetic compound found in cruciferous vegetables. It induces the production of detoxifying enzymes such as quinone reductase and glutathione S-transferase that cause xenobiotic transformation. Sulforaphane also increases the transcription of tumor suppressor proteins and inhibits histone deacetylases. It modulates inflammatory responses by suppressing the LPS-mediated expression of iNOS, COX-2, IL-1β and TNF-α.
Biochem/physiol Actions Selective inducer of phase II detoxification enzymes with anticarcinogenic properties. Organosulfur compound found in cruciferous vegetables, including broccoli.
Anticancer Research It is an isothiocyanate compound found in cruciferous vegetables like broccoli,Brussels sprouts, and cabbages. It induces phase II drug metabolism enzymes ofxenobiotic transformation and enhances the transcription of tumor suppressionproteins. It promotes cytotoxicity in p53-deleted colon cancer cells by mitochondriaandlysosome-dependent cell death. Due to the effect of sulforaphane, Bax is alsobeing increased in the presence of inhibition of JNK-induced Bcl-2 followed bymitochondrial cytochrome-C release and activation of apoptosis. Self-renewal Wnt/β-catenin signaling pathway is downregulated by sulforaphane in breast cancer stemcells. It has been reported to inhibit the activity of histone deacetylase (HDAC) andto reduce the number of polyps in Apcmin/+ mouse by inhibiting AKT and ERKsignaling and protein expression of COX-2 and cyclin-D1. Sulforaphane alsoinhibits the growth of SW620 cells by inducing apoptosis (Clarke et al. 2008). Inhuman colon cancer cells (HT-29), sulforaphane showed increased dose-dependentluciferase activity of AP-1, induced JAK activity, and inhibited NF-κB luciferaseactivation induced by LPS. It is also reported to inhibit cellular proliferation and toinduce apoptosis. In HepG2 human hepatoma cells, sulforaphane significantlyinduces the expression of the Nrf-2 protein and activation of ARE-mediatedtranscription, delays Nrf-2 degradation by inhibition of Keap1, and activates theexpression of transcription of the antioxidant HO-1 enzyme. This activation of thetranscription is partially modulated by the signaling pathway of p38 MAPK, whilep38 MAPK phosphorylates Nrf-2 and improves the binding between the proteinsNrf-2 and Keap1. In the PC-3 cells of human prostate cancer, sulforaphanesuppresses the expression regulated by NF-κB and NF-κB signaling pathway by theIκBα and IKK pathways (Wang et al. 2012).
Sulforaphane strongly inhibits the expression of TNFα, IL-1β, COX-2, and iNOSand the expression of mRNA stimulated by LPS in the primary peritonealmacrophages of wild-type mouse. The expression of HO-1 is also increasedsignificantly. The anti-inflammatory effects have been mitigated in the primaryperitoneal macrophages of Nrf2 ( / ), and therefore the anti-inflammatory activityis mainly exerted by the Nrf2 pathway in mouse peritoneal macrophages.Sulforaphane induces detoxification enzymes metabolizing drugs via phase I(modification), phase II (conjugation), and phase III (further modification andexcretion) and also increases the expression of genes that detoxify directly theexogenous carcinogenic toxins, endogenous ROS, and the genes which can recognizeand repair damaged proteins (Wang et al. 2012).
 
DL-Sulforaphane Preparation Products And Raw materials

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