505-79-3

Basic information

• Product Name: 3-(Methylthio)propyl isothiocyanate
• Synonyms: 1-isothiocyanato-3-(methylthio)-Propane;Propane, 1-isothiocyanato-3-(methylthio)-;3-(METHYLTHIO)PROPYL ISOTHIOCYANATE 98&;METHYLTHIOPROPYLISOTHIOCYANATE;Isothiocyanic Acid 3-(Methylthio)propyl Ester;IBERVERIN(RG);(3-isothiocyanatopropyl)(Methyl)sulfane;FEMA 3312
• CAS NO: 505-79-3
• Molecular Formula: C5H9NS2
• Molecular Weight: 147.26
• EINECS: 208-020-3
• Product Categories: Miscellaneous Natural Products;thioester Flavor;Alphabetical Listings;Flavors and Fragrances;M-N
• Mol File: 505-79-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 254 °C(lit.)
• Flash Point: >230 °F
• Appearance: colorless to yellow clear liquid
• Density: 1.102 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0451mmHg at 25°C
• Refractive Index: n20/D 1.564(lit.)
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: 3-(Methylthio)propyl isothiocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(Methylthio)propyl isothiocyanate(505-79-3)
• EPA Substance Registry System: 3-(Methylthio)propyl isothiocyanate(505-79-3)

Safety Data

• Hazard Codes: Xi
• Statements: 23/24/25-36/38
• Safety Statements: 26-36
• RIDADR: 2810
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 505-79-3(Hazardous Substances Data)

Usage

Description

3-Methylthiopropyl isothiocyanate has a characteristic radish odor. May be prepared from 3-methylthiopropylamine and CSCl2.

Chemical Properties

Different sources of media describe the Chemical Properties of 505-79-3 differently. You can refer to the following data:
1. 3-Methylthiopropyl isothiocyanate has a characteristic radish, irritating odor
2. Colorless liquid

Occurrence

Reported found in the hydrolysates of crucifer seeds and Lesquerella seed meal, in Iberis sempervirens seeds, in cabbage, kohlrabi, horseradish, Japanese horseradish, cauliflower and radish

Uses

Iberverin is an inducer of phase II detoxification enzymes.

Preparation

From 3-methylthiopropylamine and CSCl2.

Aroma threshold values

Detection: 5 ppb. Aroma characteristics at 0.1%: musty, radish, rooty, metallic, vegetative, sulfurous cabbage, horseradish with green mustard nuances

Taste threshold values

Taste characteristics at 5 ppm: rooty radish, sulfurous, earthy vegetative and metallic, horseradish with a methional nuance

InChI:InChI=1/C5H9NS2/c1-8-4-2-3-6-5-7/h2-4H2,1H3

Synthetic route

thiophosgene (463-71-8) + 3-methylthio-1-propanamine (4104-45-4) → iberverin (505-79-3)

Conditions	Yield
With sodium hydroxide In chloroform at 20℃; for 1h;	72%
With sodium hydroxide; chloroform
With chloroform; sodium hydrogencarbonate

3-(methylthio)propyl thiocyanate (86702-84-3) → iberverin (505-79-3)

Conditions	Yield
With tetrabutylammomium bromide; N,N-dimethyl-formamide In water for 1h; Reflux;	32.9 g

iberverin (505-79-3) + 3-chlorobenzhydrazide (1673-47-8) → 1-(3-chlorobenzoyl)-4-[(3-methylthio)propyl]thiosemicarbazide

Conditions	Yield
at 110℃; for 0.0833333h;	89%

2-[(2-aminoethyl)thio]-N,N-dimethylethanamine (82308-38-1) + iberverin (505-79-3) → 1-[2-((2-(dimethylamino)ethyl)thio)ethyl]-3-[3-(methyl-thio)propyl]thiourea

Conditions	Yield
In acetonitrile at 20℃; for 3h;	86.5%

iberverin (505-79-3) + 3-chlorophenylacetic acid hydrazide (66464-86-6) → 1-[(3-chlorophenyl)acetyl]-4-[(3-methylthio)propyl]thiosemicarbazide

Conditions	Yield
at 110℃; for 0.0833333h;	84%

ethanol (64-17-5) + iberverin (505-79-3) → N-3-(methylthio)propyl O-ethyl thiocarbamate (89855-25-4)

Conditions	Yield
for 50h; Heating;	82%

propan-1-ol (71-23-8) + iberverin (505-79-3) → N-3-(methylthio)propyl O-propyl thiocarbamate

Conditions	Yield
for 50h; Heating;	79%

iberverin (505-79-3) + N-(2-aminoethyl)-3β-hydroxy-11-oxo-olean-12-en-30-amide (912541-99-2) → N-(2-{3-[3-(methylthio)propyl]thioureido}ethyl)glycyrrhetinamide (1334318-86-3)

Conditions	Yield
In tetrahydrofuran at 20℃; for 20h;	73%
In tetrahydrofuran at 20℃;	73%

3(5)-amino-1,2,4-triazole (61-82-5) + iberverin (505-79-3) → 5-amino-N-(3-(methylthio)propyl)-1H-1,2,4-triazole-1-carbothioamide

Conditions	Yield
In acetonitrile for 8h;	68%

2-((pyridine-2-yl)methylthio)benzenamine (19980-53-1) + iberverin (505-79-3) → 1-[3-(methylthio)propyl]-3-[2-((pyridin-2-ylmethyl)-thio)-phenyl]thiourea

Conditions	Yield
In acetonitrile at 20℃; for 3h;	63.3%

2-[(2-aminoethyl)thiomethyl]pyridine (38585-75-0) + iberverin (505-79-3) → 1-[3-(methylthio)propyl]-3-[2-((pyridin-2-ylmethyl)-thio)-ethyl]thiourea

Conditions	Yield
In acetonitrile at 20℃; for 3h;	60.2%

iberverin (505-79-3) + o-aminophenyl tert-butyl sulfide (51942-41-7) → 1-[2-(tert-butylthio)phenyl]-3-[3-(methylthio)propyl]-thiourea

Conditions	Yield
In acetonitrile at 20℃; for 3h;	58.3%

iberverin (505-79-3) + 3-trifluoromethylaniline (98-16-8) → 1-[3-(methylsulfanyl)propyl]-3-[3-(trifluoromethyl)phenyl]thiourea

Conditions	Yield
In acetonitrile at 20℃; for 12h;	45%

4-Chloro-3-nitroaniline (635-22-3) + iberverin (505-79-3) → 1-(4-chloro-3-nitrophenyl)-3-[3-(methylsulfanyl)propyl]thiourea

Conditions	Yield
In acetonitrile at 20℃; for 12h;	35%

methanol (67-56-1) + iberverin (505-79-3) → N-3-(methylthio)propyl O-methyl thiocarbamate

Conditions	Yield
for 50h; Heating;	31%

iberverin (505-79-3) → (3-methylsulfanyl-propyl)-thiourea (37791-18-7)

Conditions	Yield
With ethanol; ammonia; water
With methanol; ethanol; ammonia

iberverin (505-79-3) + 4-allyl-3-thiosemicarbazide (3766-55-0) → C9H18N4S3 (17702-10-2)

iberverin (505-79-3) → iberin (505-44-2, 37791-20-1, 84104-27-8) + (S)-1-isothiocyanato-3-(methylsulfinyl)propane

Conditions	Yield
In ethanol at 27℃; for 40h; Mortierella isabellina ATCC 42613; Yield given. Title compound not separated from byproducts;
In ethanol at 27℃; for 48h; Product distribution; Helminthosporium species NRRL 4771; other isothiocyanatoalkyl methyl sulfides; var. fungi;
In ethanol at 27℃; for 48h; Helminthosporium species NRRL 4671; Yield given. Title compound not separated from byproducts;

iberverin (505-79-3) + water (7732-18-5) + N-butylamine (109-73-9) → N-butyl-N'-<3-methylsulfanyl-propyl>-thiourea

Conditions	Yield
at 25℃; Rate constant; Loesung vom pH 10.2;

iberverin (505-79-3) + water (7732-18-5) → sodium-

Conditions	Yield
at 25℃; Rate constant; Loesung vom pH 11.2;

(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)‐2‐ethyl‐3,4,10‐trihydroxy‐13‐{(2R,4R,5S,6S)‐5‐hydroxy‐4‐methoxy‐4,6‐dimethyl-tetrahydropyran‐2‐yloxy}‐11‐{(2S,3R,4S,6R)‐3‐hydroxy‐6‐methyl‐4‐methylamino-tetrahydropyran‐2‐yloxy}‐3,5,6,8,10,12,14‐heptamethyl‐1‐oxa‐6‐azacyclopentadecan‐15‐one (172617-84-4) + iberverin (505-79-3) → 2'-O,3'-N-(carbonimidoyl)-3'-N-demethyl-N'-[3-(methylthio)propyl]-9a-methyl-9a-aza-9a-homoerythromycin A (1192304-51-0)

Conditions	Yield
Stage #1: (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)‐2‐ethyl‐3,4,10‐trihydroxy‐13‐{(2R,4R,5S,6S)‐5‐hydroxy‐4‐methoxy‐4,6‐dimethyl-tetrahydropyran‐2‐yloxy}‐11‐{(2S,3R,4S,6R)‐3‐hydroxy‐6‐methyl‐4‐methylamino-tetrahydropyran‐2‐yloxy}‐3,5,6,8,10,12,14‐heptamethyl‐1‐oxa‐6‐azacyclopentadecan‐15‐one; iberverin With triethylamine In acetonitrile at 60℃; for 2h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 60℃;
Stage #1: (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)‐2‐ethyl‐3,4,10‐trihydroxy‐13‐{(2R,4R,5S,6S)‐5‐hydroxy‐4‐methoxy‐4,6‐dimethyl-tetrahydropyran‐2‐yloxy}‐11‐{(2S,3R,4S,6R)‐3‐hydroxy‐6‐methyl‐4‐methylamino-tetrahydropyran‐2‐yloxy}‐3,5,6,8,10,12,14‐heptamethyl‐1‐oxa‐6‐azacyclopentadecan‐15‐one; iberverin In acetonitrile at 60℃; for 1h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 60℃;

iberverin (505-79-3) + 3'-N-demethyl-6-O-methyl-9a-aza-9a-homoerythromycin A (906452-70-8) → 2'-O,3'-N-(carbonimidoyl)-3'-N-demethyl-N'-[3-(methylthio)propyl]-6-O-methyl-9a-aza-9a-homoerythromycin A (1192304-32-7)

Conditions	Yield
Stage #1: iberverin; 3'-N-demethyl-6-O-methyl-9a-aza-9a-homoerythromycin A With triethylamine In acetonitrile at 60℃; for 2h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 60℃;
Stage #1: iberverin; 3'-N-demethyl-6-O-methyl-9a-aza-9a-homoerythromycin A In acetonitrile at 60℃; for 2h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 60℃;

9-deoxo-9a-aza-9a-demethyl-9a-(3-aminopropyl)-9a-homoerythromycin A (92594-46-2) + iberverin (505-79-3) → C45H86N4O12S2 (905846-69-7)

Conditions	Yield
In dichloromethane at 20℃; for 48h; Combinatorial reaction / High throughput screening (HTS);

iberverin (505-79-3) + 3'-N-demethyl-6-O-methyl-9a-aza-9a-homoerythromycin A (906452-70-8) → C42H77N3O13S2

Conditions	Yield
With triethylamine In acetonitrile at 60℃; for 0.5h;

iberverin (505-79-3) + 3'-N-demethyl-6-O-methyl-9a-aza-9a-homoerythromycin A (906452-70-8) → 2'-deoxy-2'-(S)-S,3'-N-{N'-[3-(methylthio)propyl]carbonimidoyl}-3'-N-demethyl-6-O-methyl-9a-aza-9a-homoerythromycin A

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / acetonitrile / 0.5 h / 60 °C 2: 2-chloro-1-methyl-pyridinium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / -22 - 60 °C View Scheme

iberverin (505-79-3) + 3-chlorobenzhydrazide (1673-47-8) → 5-(3-chlorophenyl)-4-[(3-methylthio)propyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.08 h / 110 °C 2: sodium hydroxide / 2 h / Reflux View Scheme

iberverin (505-79-3) + 3-chlorophenylacetic acid hydrazide (66464-86-6) → 5-(3-chlorobenzyl)-4-[(3-methylthio)propyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.08 h / 110 °C 2: sodium hydroxide / 2 h / Reflux View Scheme

Upstream product

• 463-71-8 thiophosgene 
• 4104-45-4 3-methylthio-1-propanamine 
• 86702-84-3 3-(methylthio)propyl thiocyanate 

Downstream Products

• 505-44-2 iberin 

Relevant articles and documents

Structure-Activity Relationship Study on Isothiocyanates: Comparison of TRPA1-Activating Ability between Allyl Isothiocyanate and Specific Flavor Components of Wasabi, Horseradish, and White Mustard

Allyl isothiocyanate (ITC) (4) is the main pungent component in wasabi, and it generates an acrid sensation by activating TRPA1. The flavor and pungency of ITCs vary depending on the compound. However, the differences in activity to activate TRPA1 between ITCs are not known except for a few compounds. To investigate the effect of carbon chain length and substituents of ITCs, the TRPA1-activiting ability of 16 ITCs was measured. Since most of the ITCs showed nearly equal TRPA1-activiting potency, the ITC moiety is likely the predominant contributor to their TRPA1-activating abilities, and contributions of other functional groups to their activities to activate TRPA1 are comparatively small. (Figure Presented).

BIOTRANSFORMATION OF ORGANIC SULFIDES. PART 7. FORMATION OF CHIRAL ISOTHIOCYANATO SULFOXIDES AND RELATED COMPOUNDS BY MICROBIAL BIOTRANSFORMATION

The fungi Helminthosporium species NRRL 4671 and Mortierella isabellina ATCC 42613 have been used for the biotransformation of a series of isothiocyanatoalkyl methyl sulfides and their synthetic precursors, ω-(methylthio)alkylphthalimides.H. species gave predominantly (S) sulfoxides in all cases; M. isabellina gave (R) isothiocyanatoalkyl methyl sulfoxides, but in the case of two ω-(methylthio)alkylphthalimides substantial conversion of sulfoxide to sulfone resulted in the isolation of the former with predominant (S) configuration.A correction is made of the previously reported configurations of two biotransformation products (Tetrahedron: Asymmetry, 1994, 5, 1129).