DL-Sulforaphane supplier | CasNO.4478-93-7

Name
DL-SULFORAPHANE
EINECS
CAS No. 4478-93-7
Article Data27
CAS DataBase
Density 1.17 g/cm³
Solubility DMSO: 40 mg/mL, soluble
Melting Point
Formula C₆H₁₁NOS₂
Boiling Point 368.2 °C at 760 mmHg
Molecular Weight 177.291
Flash Point 176.5 °C
Transport Information
Appearance Light yellow liquid
Safety 23-24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Sulforaphane;4-Methylsulfinylbutyl isothiocyanate;Sulforaphan (6CI);Isothiocyanicacid, 4-(methylsulfinyl)butyl ester (8CI);
PSA 80.73000
LogP 2.11360

Synthetic route

: 4430-36-8
erucin

: 4478-93-7
D,L-sulforaphane

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 0.5h;	100%
With dihydrogen peroxide In methanol	100%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at -5℃; for 3h;	95%

: 463-71-8
thiophosgene

: 84104-30-3
(+/-)-1-amino-4-(methylsulfinyl)butane

: 4478-93-7
D,L-sulforaphane

Conditions

Conditions	Yield
With sodium hydroxide In chloroform; water for 1h;	85.7%
With sodium hydroxide In chloroform for 0.583333h;	57%
With sodium hydroxide In chloroform at 20℃; for 1h;	52%
With sodium hydrogencarbonate In dichloromethane

: 75-15-0
carbon disulfide

: 84104-30-3
(+/-)-1-amino-4-(methylsulfinyl)butane

: 4478-93-7
D,L-sulforaphane

Conditions

Conditions	Yield
Stage #1: carbon disulfide; (+/-)-1-amino-4-(methylsulfinyl)butane With triethylamine In ethanol at 20℃; for 0.5h; Inert atmosphere; Stage #2: With dmap; di-tert-butyl dicarbonate In ethanol at 0 - 20℃; for 2.25h;	79%

: 2799-72-6
3-Chloropropyl isothiocyanate

: 15590-23-5
sodium methylsulfinylmethanide

: 4478-93-7
D,L-sulforaphane

Conditions

Conditions	Yield
In tetrahydrofuran at -30℃; for 3h; Solvent; Temperature;	64.7%

: 4-methylsulfinylbutyl glucosinolate

A: 2280-44-6
D-Glucose

B: 4478-93-7
D,L-sulforaphane

Conditions

Conditions	Yield
With myrosinase; buffer pH = 6.5 at 37℃;

methyl-<4-amino-butyl>-sulfoxide: methyl-<4-amino-butyl>-sulfoxide

: 4478-93-7
D,L-sulforaphane

: sulforaphane cysteine

A: 52-90-4
L-Cysteine

B: 4478-93-7
D,L-sulforaphane

Conditions

Conditions	Yield
In water; dimethyl sulfoxide at 37℃; pH=7.4; Kinetics; Product distribution; Further Variations:; pH-values;

: C11H20N2O5S3

A: 4478-93-7
D,L-sulforaphane

B: N-acetyl-L-cysteine

Conditions

Conditions	Yield
In water; dimethyl sulfoxide at 37℃; pH=7.4; Kinetics; Product distribution; Further Variations:; pH-values;

: (11R,16S)-16-amino-11-((carboxymethyl)carbamoyl)-13-oxo-8-methylsulfinyl-2,9-dithia-7,12-diazaheptadecan-17-oic acid

A: 4478-93-7
D,L-sulforaphane

B: 70-18-8
GLUTATHIONE

Conditions

Conditions	Yield
In water; dimethyl sulfoxide at 37℃; pH=7.4; Kinetics; Product distribution; Further Variations:; pH-values;

: 4-methylsulfinylbutyl glucosinolate

: 4478-93-7
D,L-sulforaphane

Conditions

Conditions	Yield
With phosphate buffer; myrosinase at 37℃; pH=6.5;

: 55021-77-7
4-(methylthio)-1-butylamine

: 4478-93-7
D,L-sulforaphane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 12.5 mmol / sodium hydroxide / CHCl3 2: 100 percent / m-chloroperbenzoic acid / CH2Cl2 / 0.5 h View Scheme
Multi-step reaction with 2 steps 1: 64 percent / aq. H2O2; H2SO4; i-PrOH / methanol / 2 h / 20 °C 2: 57 percent / aq. NaOH / CHCl3 / 0.58 h View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid; dihydrogen peroxide / methanol; water; isopropyl alcohol / 3 h / 20 °C 2: sodium hydroxide / chloroform / 1 h / 20 °C View Scheme

: 52096-68-1
2-<2-(Methylthio)butyl>-1H-isoindole-1,3(2H)-dione

: 4478-93-7
D,L-sulforaphane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 21.1 mmol / hydrazine monohydrate; hydrogen chloride / ethanol / 2 h / 75 °C 2: 12.5 mmol / sodium hydroxide / CHCl3 3: 100 percent / m-chloroperbenzoic acid / CH2Cl2 / 0.5 h View Scheme
Multi-step reaction with 3 steps 1.1: hydrazine hydrate / methanol / 70 °C 2.1: triethylamine / tetrahydrofuran / 0 - 20 °C 2.2: 0.5 h / 0 - 20 °C 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.08 h / -10 - 0 °C View Scheme
Multi-step reaction with 3 steps 1: hydrazine hydrate / ethanol / 3 h / Reflux 2: sodium hydroxide / dichloromethane / 3.5 h / 0 - 20 °C / Inert atmosphere 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: acetic acid; dihydrogen peroxide 2: hydrazine hydrate / ethanol / Reflux 3: sodium hydrogencarbonate / dichloromethane View Scheme

: 59121-24-3
4-(methylthio)butyronitrile

: 4478-93-7
D,L-sulforaphane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 63 percent / BH3 / tetrahydrofuran / 20 °C 2: 64 percent / aq. H2O2; H2SO4; i-PrOH / methanol / 2 h / 20 °C 3: 57 percent / aq. NaOH / CHCl3 / 0.58 h View Scheme
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / diethyl ether / 0.5 h / Reflux 2: sulfuric acid; dihydrogen peroxide / methanol; water; isopropyl alcohol / 3 h / 20 °C 3: sodium hydroxide / chloroform / 1 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: lithium aluminium tetrahydride / diethyl ether / 3 h / Inert atmosphere; Reflux 2.1: dihydrogen peroxide / 2,2,2-trifluoroethanol / 1.33 h / 0 - 20 °C / Inert atmosphere 3.1: triethylamine / ethanol / 0.5 h / 20 °C / Inert atmosphere 3.2: 2.25 h / 0 - 20 °C View Scheme

: 463-71-8
thiophosgene

: 4478-93-7
D,L-sulforaphane

Conditions

Conditions	Yield
Stage #1: 4-(methylthio)-1-butylamine With dihydrogen peroxide In water; acetone at 50℃; Stage #2: thiophosgene With sodium hydroxide In dichloromethane; water; acetone for 0.5h;

: 21414-41-5
4-(methylsulfinyl)butyl-glucosinolate

: 4478-93-7
D,L-sulforaphane

Conditions

Conditions	Yield
With myrosinase; water

: 1350472-27-3
tert-butyl [4-(methylsulfanyl)butyl]carbamate

: 4478-93-7
D,L-sulforaphane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogenchloride / dichloromethane / 2 h / 20 °C 2.1: triethylamine / tetrahydrofuran / 1.5 h / 0 - 20 °C 2.2: 0.5 h / 0 - 20 °C 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.42 h / 0 °C View Scheme
Multi-step reaction with 3 steps 1: hydrogenchloride / dichloromethane / 2 h / 20 °C 2: triethylamine / dichloromethane / 12 h / 0 - 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.42 h / 0 °C View Scheme

: 4-(methylsulfanyl)butan-1-amine hydrochloride

: 4478-93-7
D,L-sulforaphane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine / tetrahydrofuran / 1.5 h / 0 - 20 °C 1.2: 0.5 h / 0 - 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.42 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 12 h / 0 - 20 °C 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.42 h / 0 °C View Scheme

: (R,S)S-glucoraphanin

: 4478-93-7
D,L-sulforaphane

Conditions

Conditions	Yield
With myrosinase In aq. phosphate buffer pH=7.2; Enzymatic reaction;

: 1-[5-(methylsulfinyl)-N-(sulfonatooxy)pentanimidoyl]-1-thio-β-D-glucopyranose

: 4478-93-7
D,L-sulforaphane

Conditions

Conditions	Yield
With ascorbic acid at 38℃; for 0.5h; pH=7.5; Reagent/catalyst; Enzymatic reaction;	120.16 μmol

: S-methyltetrahydrothiophenium fluoroborate

: 4478-93-7
D,L-sulforaphane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium azide / N,N-dimethyl-formamide / 16 h / 60 °C / Green chemistry 2.1: triphenylphosphine / diethyl ether / 3 h / 20 °C / Green chemistry 2.2: 1 h / 20 °C / Green chemistry 3.1: dihydrogen peroxide; acetic acid / 1 h / 20 °C / Green chemistry View Scheme
Multi-step reaction with 3 steps 1.1: sodium azide / N,N-dimethyl-formamide / 16 h / 60 °C 2.1: triphenylphosphine / diethyl ether / 3 h / 20 °C 2.2: 1 h / 20 °C 3.1: dihydrogen peroxide; acetic acid / 1 h / 20 °C View Scheme

: 57775-01-6
1-azido-(4-methylsulfenyl)butane

: 4478-93-7
D,L-sulforaphane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triphenylphosphine / diethyl ether / 3 h / 20 °C / Green chemistry 1.2: 1 h / 20 °C / Green chemistry 2.1: dihydrogen peroxide; acetic acid / 1 h / 20 °C / Green chemistry View Scheme

: 20582-85-8
4-(methylthio)-1-butanol

: 4478-93-7
D,L-sulforaphane

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / 1 h / -10 - 20 °C 2.1: sodium azide; tetrabutylammomium bromide / acetone; water / 6 h / Reflux; Inert atmosphere 3.1: triphenylphosphine / toluene / 4 h / 0 - 20 °C / Inert atmosphere 3.2: 24 h / 20 °C 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / -5 °C View Scheme

: 4-methylthio-1-butyl methanesulfonate

: 4478-93-7
D,L-sulforaphane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium azide; tetrabutylammomium bromide / acetone; water / 6 h / Reflux; Inert atmosphere 2.1: triphenylphosphine / toluene / 4 h / 0 - 20 °C / Inert atmosphere 2.2: 24 h / 20 °C 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / -5 °C View Scheme

: 163956-72-7
N-(4-methanesulfinyl-butyl)-phthalimide

: 4478-93-7
D,L-sulforaphane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrazine hydrate / ethanol / Reflux 2: sodium hydrogencarbonate / dichloromethane View Scheme

: 51-67-2
tyrosamine

: 4478-93-7
D,L-sulforaphane

: C14H22N2O2S2

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 10h; Inert atmosphere;	98.62%

: 84104-30-3
(+/-)-1-amino-4-(methylsulfinyl)butane

: 4478-93-7
D,L-sulforaphane

: N,N’-di-(4-methylsulfinylbutyl)thiourea

Conditions

Conditions	Yield
In dichloromethane for 1h; Reflux;	97%

: 109-01-3
1-methyl-piperazine

: 4478-93-7
D,L-sulforaphane

: 75-09-2
dichloromethane

: 1356472-66-6
4-methyl-N-(4-(methylsulfinyl)-butyl)piperazine-1-carbothioamide

Conditions

Conditions	Yield
In dichloromethane for 1h; Reflux;	97%

...Expand

: 110-91-8
morpholine

: 4478-93-7
D,L-sulforaphane

: 1356346-82-1
N-(4-(methylsulfinyl)butyl)-morpholine-4-carbothioamide

Conditions

Conditions	Yield
In dichloromethane for 1h; Reflux;	95%

: 50541-93-0
4-amino-1-benzylpiperidine

: 4478-93-7
D,L-sulforaphane

: 1356346-85-4
1-(1-benzyl-piperidin-4-yl)-3-4-(methylsulfinyl)butyl thiourea

Conditions

Conditions	Yield
In dichloromethane for 1h; Reflux;	93%

: 4478-93-7
D,L-sulforaphane

: 6258-60-2
p-methoxybenzylmercaptan

: 4-methoxybenzyl (4-(methylsulfinyl)butyl)carbamodithioate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water at 20℃; Inert atmosphere;	91.9%

: 4478-93-7
D,L-sulforaphane

: 6258-66-8
(4-chlorophenyl)methanethiol

: p-chlorobenzyl N-[4-(methylsulfinyl)butyl]carbamodithioate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water at 20℃; Inert atmosphere;	91.8%

: 4478-93-7
D,L-sulforaphane

: 7149-10-2
vanillylamine hydrochloride

: C14H22N2O3S2

Conditions

Conditions	Yield
Stage #1: vanillylamine hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: D,L-sulforaphane In N,N-dimethyl-formamide at 20℃; for 10h;	89%

: 4478-93-7
D,L-sulforaphane

: C8H17NO2S

: C14H28N2O3S3

Conditions

Conditions	Yield
With dmap In dichloromethane at 20℃; for 10h; Inert atmosphere;	88.7%

: 4478-93-7
D,L-sulforaphane

: 75-08-1
ethanethiol

: ethyl (4-(methylsulfinyl)butyl)carbamodithioate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water at 20℃; for 5h;	87.5%
With sodium hydrogencarbonate In ethanol; water at 20℃; Inert atmosphere;	87.5%

: 64-17-5
ethanol

: 4478-93-7
D,L-sulforaphane

: 1356472-67-7
O-ethyl 4-(methylsulfinyl)butylcarbamothioate

Conditions

Conditions	Yield
Reflux; Inert atmosphere;	84%

: 4478-93-7
D,L-sulforaphane

: 106-45-6
para-thiocresol

: p-tolyl (4-(methylsulfinyl)butyl)carbamodithioate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water at 20℃; Inert atmosphere;	83.3%

: 4410-99-5
2-mercaptophenylethane

: 4478-93-7
D,L-sulforaphane

: phenethyl (4-(methylsulfinyl)butyl)carbamodithioate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water at 20℃; Inert atmosphere;	81.1%

: 4478-93-7
D,L-sulforaphane

: L-lysine-[(13)C6(15)N2] hydrochloride

: N6-({[3-(methylsulfinyl)butyl]amino}carbonothioyl)[(13)C6(15)N2]lysine

Conditions

Conditions	Yield
Stage #1: L-lysine-[(13)C6(15)N2] hydrochloride With copper(II) carbonate; sodium hydroxide In water at 100℃; for 0.333333h; Stage #2: D,L-sulforaphane In 1,4-dioxane; water at 20℃; for 4h; Stage #3: With sodium sulfide In 1,4-dioxane; water at 20℃; for 0.166667h;	81%

: 4478-93-7
D,L-sulforaphane

: 10016-20-3
alpha cyclodextrin

: 1498229-87-0
sulforaphane-cyclodextrin complex

Conditions

Conditions	Yield
Stage #1: alpha cyclodextrin In water at 55℃; Inert atmosphere; Cooling with ice; Stage #2: D,L-sulforaphane In water at 20℃; for 16h;	78.5%

: 4478-93-7
D,L-sulforaphane

: 3-(perfluorophenyl)-1,4,2-dioxazole-5-one

: C13H11F5N2O2S2

Conditions

Conditions	Yield
With carbonyl(5,10,15,20-tetraphenylporphyrinato)ruthenium(II) In toluene at 20℃; for 4h;	76%

: 513-53-1
1-methyl-1-propanethiol

: 4478-93-7
D,L-sulforaphane

: sec-butyl (4-(methylsulfinyl)butyl)carbamodithioate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water at 20℃; Inert atmosphere;	75%

: 4478-93-7
D,L-sulforaphane

: 2396-68-1
4-t-butylbenzenethiol

: 4-(tert-butyl)phenyl (4-(methylsulfinyl)butyl)carbamodithioate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water at 20℃; Inert atmosphere;	72.8%

: 4478-93-7
D,L-sulforaphane

: 4498-99-1
4-methylbenzylthiol

: 4-methylbenzyl (4-(methylsulfinyl)butyl)carbamodithioate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water at 20℃; Inert atmosphere;	72.3%

: 4478-93-7
D,L-sulforaphane

: 2935-90-2
Methyl 3-mercaptopropionate

: methyl 3-(((4-(methylsulfinyl)butyl)carbamothioyl)thio)propanoate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water at 20℃; Inert atmosphere;	70.8%

: 4478-93-7
D,L-sulforaphane

: 616-91-1
N-acetylcystein

: N-acetyl-S-{N-[4-(methylsulfinyl)butyl]thiocarbamoyl}-L-cysteine

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water	69.5%
With sodium hydroxide In ethanol; water at 23℃; for 2h; pH=7 - 8;	36%

: 4478-93-7
D,L-sulforaphane

: 504-84-7
erysolin

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at -20 - 20℃; for 3h; Inert atmosphere;	66%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 2h;	60%

: 4478-93-7
D,L-sulforaphane

: C8H19NO2S

: C14H30N2O3S3

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 10h; Inert atmosphere;	64.5%
With triethylamine In dichloromethane at 20℃; for 10h; Inert atmosphere;	64.5%

: 4478-93-7
D,L-sulforaphane

: 17042-24-9
2-mercapto-pentan-3-one

: 3-oxopentan-2-yl (4-(methylsulfinyl)butyl)carbamodithioate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water at 20℃; Inert atmosphere;	63.6%

: 696-63-9
4-Methoxybenzenethiol

: 4478-93-7
D,L-sulforaphane

: 4-methoxyphenyl (4-(methylsulfinyl)butyl)carbamodithioate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water at 20℃; Inert atmosphere;	63.2%

DL-Sulforaphane Specification

The CAS registry number of DL-Sulforaphane is 4478-93-7. The IUPAC name is 1-isothiocyanato-4-methylsulfinylbutane. In addition, the molecular formula is C₆H₁₁NOS₂ and the molecular weight is 177.29. It is also called Butane,1-isothiocyanato-4-(methylsulfinyl)-. What's more, it is a kind of light yellow liquid and belongs to the classes of Sulphur Derivatives; Miscellaneous Natural Products; All Inhibitors; Inhibitors; Sulfur & Selenium Compounds; Antitumour.

Physical properties about this chemical are: (1)ACD/LogP: 0.23; (2)ACD/LogD (pH 5.5): 0.23; (3)ACD/LogD (pH 7.4): 0.23; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 31.61; (7)ACD/KOC (pH 7.4): 31.61; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 5; (10)Polar Surface Area: 80.73 Å²; (11)Index of Refraction: 1.566; (12)Molar Refractivity: 49.16 cm³; (13)Molar Volume: 150.6 cm³; (14)Polarizability: 19.49 ×10^-24cm³; (15)Surface Tension: 46.2 dyne/cm; (16)Density: 1.17 g/cm³; (17)Flash Point: 176.5 °C; (18)Enthalpy of Vaporization: 59.06 kJ/mol; (19)Boiling Point: 368.2 °C at 760 mmHg; (20)Vapour Pressure: 2.75E-05 mmHg at 25°C.

Uses of DL-Sulforaphane: it can be used to treat esophageal cancer, lung and colon cancer, breast cancer, liver cancer and colorectal cancer. And it can indirectly increase the oxidation resistance of animal cell.

When you are using this chemical, please be cautious about it as the following:
During using it, do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer). And you should avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: S=C=N\CCCCS(=O)C
(2)InChI: InChI=1/C6H11NOS2/c1-10(8)5-3-2-4-7-6-9/h2-5H2,1H3
(3)InChIKey: SUVMJBTUFCVSAD-UHFFFAOYAY

Product Name

DL-SULFORAPHANE

Synthetic route

DL-Sulforaphane Specification

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