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Environmental fate & pathways

Hydrolysis

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Administrative data

Endpoint:
hydrolysis
Type of information:
experimental study
Adequacy of study:
weight of evidence
Study period:
1969
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
data from handbook or collection of data

Data source

Reference
Reference Type:
publication
Title:
Decomposition of Allyl Isothiocyanate in Aqueous Solution
Author:
Shunro KAWAKISHI and Mitsuo NAMIKI
Year:
1969
Bibliographic source:
Agr. Biol. Chem., Vol. 33, No. 3, p. 452-459, 1969

Materials and methods

Principles of method if other than guideline:
Allyl isothiocyanate was gradually decomposed in aqueous solution to produce a garlic like odor. Details are reported in the publication.
GLP compliance:
not specified

Test material

Reference
Name:
Unnamed
Type:
Constituent
Test material form:
liquid
Specific details on test material used for the study:
Allyl isothiocyanate is gradually decomposed in aqueous solution to produce a garlic like odor. The decomposition of this isothiocyanate is not based on hydrolysis of R-NCS as in the case of p-hydroxybenzyl isothiocyanate, but the addition reaction on -N=C=S.
Four substances formed with the decomposition of the isothiocyanate were isolated, and their chemical constitutions were clarified. Allyl isothiocyanate was decomposed to allyl allyldithiocarbamate, which was degraded to diallyl tetra- and penta-sulfide, and this poly-sulfide was further degraded to paraffin like hydrocarbon and sulfur. Moreover, N,N'-diallylthiourea was produced by the addition reaction of allylamine, formed from the isothiocyanate by action of water, to residual isothiocyanate.

Results and discussion

Transformation products:
yes
Identity of transformation productsopen allclose all
No.:
#1
Reference
Reference substance name:
Unnamed
IUPAC name:
prop-2-enyl carbamodithioate
Identifier:
CAS number
Identity:
50586-78-2
No.:
#2
Reference
Reference substance name:
Unnamed
IUPAC name:
3-(prop-2-enyltetrasulfanyl)prop-1-ene
Identifier:
CAS number
Identity:
2444-49-7
No.:
#3
Reference
Reference substance name:
Unnamed
IUPAC name:
3-(prop-2-enylpentasulfanyl)prop-1-ene
Identifier:
CAS number
Identity:
118686-45-6
No.:
#4
Reference
Reference substance name:
Unnamed
IUPAC name:
1,3-bis(prop-2-enyl)thiourea
Identifier:
CAS number
Identity:
6601-20-3
No.:
#5
Reference
Reference substance name:
Unnamed
Inventory number:
InventoryMultipleMappingImpl [inventoryEntryValue=EC 203-463-9]
IUPAC name:
prop-2-en-1-amine
Identity:
2-Propen-1-amine
Identity:
2-propen-1-amine
CAS number:
107-11-9
Molecular formula:
C3H7N
Molecular weight:
57.094
SMILES notation:
NCC=C
InChl:
InChI=1/C3H7N/c1-2-3-4/h2H,1,3-4H2
No.:
#6
Reference
Reference substance name:
Unnamed
IUPAC name:
n.a.
No.:
#6
Reference
Reference substance name:
Unnamed
Inventory number:
InventoryMultipleMappingImpl [inventoryEntryValue=EC 231-722-6]
IUPAC name:
sulfur
CAS number:
7704-34-9
Molecular formula:
S
Molecular weight:
ca. 32.06
SMILES notation:
S
InChl:
InChI=1/H2S/h1H2
Dissipation half-life of parent compound
Temp.:
37 °C
Remarks on result:
other: the substance is slowly decomposed and its residual amounts were reached to about 25% of the initial state within 10 days.

Applicant's summary and conclusion

Conclusions:
Allyl isothiocyanate is gradually decomposed in aqueous solution to produce a garlic like odor. The decomposition of this isothiocyanate is not based on hydrolysis of R-NCS as in the case of p-hydroxybenzyl isothiocyanate, but the addition reaction on -N=C=S.