DL-Goitrin
PubChem CID
3034683
Structure
Molecular Formula
Synonyms
- DL-Goitrin
- Goitrin
- 13190-34-6
- 2-Oxazolidinethione, 5-ethenyl-
- 5-Vinyloxazolidine-2-thione
Molecular Weight
129.18 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2005-03-27
- Modify:2025-01-18
Description
5-ethenyl-1,3-oxazolidine-2-thione is a member of the class of oxazolidines that is 1,3-oxazolidine substituted by sulfanylidene and ethenyl groups at positions 2 and 5, respectively. It is a member of oxazolidines and an olefinic compound.
DL-Goitrin has been reported in Isatis tinctoria with data available.
See also: (S)-5-Vinyloxazolidine-2-thione (annotation moved to).
Chemical Structure Depiction
5-ethenyl-1,3-oxazolidine-2-thione
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
InChI=1S/C5H7NOS/c1-2-4-3-6-5(8)7-4/h2,4H,1,3H2,(H,6,8)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
UZQVYLOFLQICCT-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
C=CC1CNC(=S)O1
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C5H7NOS
Computed by PubChem 2.2 (PubChem release 2021.10.14)
500-12-9 (L)
- 5-vinyl-2-thiooxazolidone
- 5-vinyloxazolidin-2-thione
- 5-vinyloxazolidine-2-thione
- epigoitrin
- goitrin
- goitrin, (+-)-isomer
- goitrin, (R)-isomer
- goitrin, (S)-isomer
- DL-Goitrin
- Goitrin
- 13190-34-6
- 2-Oxazolidinethione, 5-ethenyl-
- 5-Vinyloxazolidine-2-thione
- 5-ethenyl-1,3-oxazolidine-2-thione
- 5-Ethenyl-2-oxazolidinethione
- 5-Vinyl-2-oxazolidinethione
- 5-vinylthiooxazolidone
- (+/-)-goitrin
- 5-vinyloxazolidinethione
- 5-vinyl-2-thiooxazolidone
- 5-vinyl-2-thiooxazolidinone
- O8KVD7J2P5
- 5-vinyl-2-oxazolidine-2-thione
- ( -)-Goitrin
- (+-)-Goitrin
- EINECS 236-145-3
- UNII-O8KVD7J2P5
- (plusmn)-goitrin
- (R,S)-Goitrin
- 2-Oxazolidinethione, 5-vinyl-, DL-
- DL-Goitrin (Standard)
- GOITRIN, DL-
- 5-Vinyloxazolidone-2-thione
- 5-vinyl-oxazolidine-2-thione
- SCHEMBL340219
- CHEMBL508652
- GOITRIN, (+/-)-
- GTPL12495
- HY-N5056R
- DTXSID10274235
- CHEBI:183227
- HY-N5056
- 5-vinyl-4,5-dihydrooxazol-2-thiol
- MFCD00015467
- s3251
- AKOS025402176
- 2-OXAZOLIDINETHIONE, 5-VINYL-
- 5-Vinyl-1,3-oxazolidine-2-thione #
- AC-6038
- 13997-13-2
- DA-53671
- LS-13042
- CS-0032210
- NS00052048
- J-006081
- Q5577929
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
129.18 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
129.02483502 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
129.02483502 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
53.4 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
8
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
124
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)
Solid; [Merck Index]
Large prisms from ether
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 804
50 °C
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 804
Stable in alkali, but not in acid.
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 804
pKa = 10.5
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 804
Biological Agents -> Plant Toxins
NIST Number
136081
Library
Main library
Total Peaks
57
m/z Top Peak
129
m/z 2nd Highest
68
m/z 3rd Highest
39
Thumbnail
NIST Number
196284
Library
Main library
Total Peaks
71
m/z Top Peak
129
m/z 2nd Highest
68
m/z 3rd Highest
57
Thumbnail
Accession ID
Authors
Tobias Schulze, Martin Krauss, Helmholtz Centre for Environmental Research GmbH - UFZ, Leipzig, Germany
Instrument
LTQ Orbitrap XL Thermo Scientific
Instrument Type
LC-ESI-ITFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
10% (nominal)
Fragmentation Mode
HCD
Column Name
Kinetex Evo C18 2.6 um 50x2.1 mm, Phenomenex
Retention Time
1.217 min
Precursor m/z
130.0321
Precursor Adduct
[M+H]+
Top 5 Peaks
130.032 999
70.0649 403
License
CC0
Accession ID
Authors
Tobias Schulze, Martin Krauss, Helmholtz Centre for Environmental Research GmbH - UFZ, Leipzig, Germany
Instrument
LTQ Orbitrap XL Thermo Scientific
Instrument Type
LC-ESI-ITFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
15% (nominal)
Fragmentation Mode
HCD
Column Name
Kinetex Evo C18 2.6 um 50x2.1 mm, Phenomenex
Retention Time
1.217 min
Precursor m/z
130.0321
Precursor Adduct
[M+H]+
Top 5 Peaks
130.032 999
70.0648 526
License
CC0
Accession ID
Authors
EPA CCTE and Agilent Technologies
Instrument Type
ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
20
Precursor m/z
128.0175581
Precursor Adduct
[M-H]-
Top 5 Peaks
57.975693 999
71.991343 136
License
CC BY
Accession ID
Authors
EPA CCTE and Agilent Technologies
Instrument Type
ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
40
Precursor m/z
128.0175581
Precursor Adduct
[M-H]-
Top 5 Peaks
57.975693 999
71.991343 50
License
CC BY
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Stereo Count
Same Isotope Count
Same Parent, Connectivity Count
Same Parent, Stereo Count
Same Parent, Isotope Count
Similar Compounds (2D)
Similar Conformers (3D)
Same Count
(S)-5-Vinyloxazolidine-2-thione (annotation moved to)
Goitrin, (DL);13190-34-6
Antithyroid Agents
Agents that are used to treat hyperthyroidism by reducing the excessive production of thyroid hormones. (See all compounds classified as Antithyroid Agents.)
A total of six cows, divided into 3 groups, were fed various amounts of rape cake containing 6 g of goitrin/kg over a period of 7 days. The cows were milked twice a day ... . When rape cake was fed at 0.39, 1.9 and 3.9% resp. of the total feed this resulted in medium goitrin values of 37, 163 and 707 ug/l milk. These values correspond to a transfer of about 0.1% of the original progoitrin content in the feed. 12 h after the last rape feeding the amount of goitrin in the milk was below the detection limit of 7 ppb.
A wide variety of chemicals, drugs, and other xenobiotics affect the second step in thyroid hormone biosynthesis. The stepwise binding of iodide to the tyrosyl residues in thyroglobulin requires oxidation of inorganic iodide (I2) to molecular (reactive) iodine (I2) by the thyroid peroxidase present in the luminal aspect (microvillar membranes) of follicular cells and adjacent colloid. Classes of chemicals that inhibit the organification of thyroglobulin include ... the thionamides (such as ... goitrin)... .
Klaassen, C.D. (ed). Casarett and Doull's Toxicology. The Basic Science of Poisons. 6th ed. New York, NY: McGraw-Hill, 2001., p. 726
Sources/Uses
A thyroid toxin found in the seeds of various Brassica and Cruciferae species; [Merck Index]
Merck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.
An antithyroid cmpd isolated from seeds of different species of Brassica, Cruciferae: Astwood et al., J. Biol. Chem. 181,121 (1949); Greer, J. Am. Chem. Soc., 78, 1260 (1956)
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 804
Goitrin is a potent goitrogen that has been shown to induce glutathione S-transferase (GST) activity and to increase aflatoxin detoxification.
Kelly M et al; Food and Chemical Toxicology 33(2): 129-137 (1995)
goitrin --a naturally occurring compound in cruciferous vegetables and rape--could be easily nitrosated by treatment with nitrite under stomach conditions, yielding with loss of sulfur the N-nitroso- oxazolidone 4. This product has a mutagenicity pattern and potency similar to that of N-nitroso-N-methyl-N'- nitroguanidine (MNNG) in the Ames Salmonella/mammalian microsome test.
Luthy J et al; Experientia 40(5): 452-453 (1984)
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/
Bronstein, A.C., P.L. Currance; Emergency Care for Hazardous Materials Exposure. 2nd ed. St. Louis, MO. Mosby Lifeline. 1994., p. 139
Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
Bronstein, A.C., P.L. Currance; Emergency Care for Hazardous Materials Exposure. 2nd ed. St. Louis, MO. Mosby Lifeline. 1994., p. 139
/LABORATORY ANIMALS: Acute Exposure/ Antithyroid activity of orally administered goitrin was assessed by parallel-line assay in chicks using four indices. The relative potency of goitrin in chicks was estimated to be approximately 0.31 times the potency of PTU in causing enlargement of thyroid gland, 0.06 times in effect on depression in plasma thyroid hormone, and 0.08 times in inhibitory effects on biosynthesis of thyroid hormone in the gland. It might be concluded that thyroid hormone synthesis is not so much suppressed to the degree expected from the enlargement of thyroid gland when goitrin is administered orally to the chick.
Akiba Y et al; Poult Sci 55(2): 716-719 (1976)
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Effects of dietary R-goitrin (200 ppm) ... on GST activity, binding of aflatoxin B1 (AFB1) to DNA, in vivo, and biliary excretion of thiol conjugates of AFB1 in rats were studied. Increases of GST activities (1.9-fold) were accompanied by reductions in AFB1-DNA binding (43%) and increases (1.7-fold) in biliary excretion of AFB1-thiol conjugates in R-goitrin ...groups... . Microsomal aflatoxin 8,9-epoxidase activities were not increased in either treatment group.
Chang Y et al; Carcinogenesis 8(4): 585-590 (1987)
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In male and female rats, R-goitrin treatment increased the relative liver weights; in some of the enlarged livers a high incidence of mitotic figures was observed. R-goitrin treatment increased the relative thyroid weight, more in male rats than in females. The thyroids of R-goitrin treated rats were either hyperplastic or had most follicles filled with pale-staining colloid and rarely follicles with normal, well-stained colloid. At certain doses, R-goitrin increased serum triglycerides, cholesterol, total protein, albumin and calcium, but it decreased serum thyroxine and urea. However, most of these changes in serum chemistry were small. R-goitrin caused a temporary increase in urinary ascorbic acid output in both sexes, but the liver ascorbic acid level was increased only in female rats. The duration of pentobarbital-induced sleep was significantly prolonged by R-goitrin pretreatment only in male rats.
Nishie K et al; Food and Chem Toxicol 20 (3): 279-287 (1982)
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Diets containing 500 g high-glucosinolate rapeseed meal/kg or an equivalent amount of soybean meal as the only protein supplement were fed to layer-type chickens and two broiler strains from 1 to 56 days of age. Additional groups of the former were maintained on the diets until they were 16 and 28 days old. The rapeseed meal produced thyroid hypertrophy in all strains but reduced the growth rate of only one of the broiler strains. The livers of chickens fed on rapeseed meal were enlarged and DNA analysis indicated hyperplasia, but no macroscopic lesions were found. The activities of aspartate transaminase, lactate dehydrogenase and alkaline phosphatase in the plasma were increased by rapeseed meal, suggesting liver damage. In all strains, feeding rapeseed meal increased plasma total protein, albumin and cholesterol and decreased urate. Hyperglycemia accompanied by a decrease in plasma triglycerides occurred in the layer strain. Through its extra-thyroidal toxicity (-)5-vinyl-oxazolidine-2-thione (goitrin) was probably responsible for most of these changes./rapeseed/
Pearson AW et al; Br Poult Sci 24(3): 417-427 (1983)
For more Non-Human Toxicity Excerpts (Complete) data for GOITRIN (10 total), please visit the HSDB record page.
When rape cake was fed /to cows/ at 0.39, 1.9 and 3.9% resp. of the total feed this resulted in medium goitrin values of 37, 163 and 707 micrograms/l milk. These values correspond to a transfer of about 0.1% of the original progoitrin content in the feed. 12 h after the last rape feeding the amount of goitrin in the milk was below the detection limit of 7 ppb.
Bachmann M et al; Z Lebensm Unters Forsch 181 (5): 375-8 (1985)
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=UZQVYLOFLQICCT-UHFFFAOYSA-N
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
- CAS Common ChemistryLICENSEThe data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.https://creativecommons.org/licenses/by-nc/4.0/
- ChemIDplus2-Oxazolidinethione, 5-vinyl-, DL-https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0013997132ChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
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- European Chemicals Agency (ECHA)LICENSEUse of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.https://echa.europa.eu/web/guest/legal-notice5-vinyloxazolidine-2-thionehttps://echa.europa.eu/substance-information/-/substanceinfo/100.032.845
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- Hazardous Substances Data Bank (HSDB)
- ChEBI5-ethenyl-1,3-oxazolidine-2-thionehttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:183227
- LOTUS - the natural products occurrence databaseLICENSEThe code for LOTUS is released under the GNU General Public License v3.0.https://lotus.nprod.net/DL-Goitrinhttps://www.wikidata.org/wiki/Q5577929LOTUS Treehttps://lotus.naturalproducts.net/
- ChEMBLLICENSEAccess to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).http://www.ebi.ac.uk/Information/termsofuse.htmlChEMBL Protein Target Treehttps://www.ebi.ac.uk/chembl/g/#browse/targets
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- Japan Chemical Substance Dictionary (Nikkaji)
- Natural Product Activity and Species Source (NPASS)
- MassBank Europe
- MassBank of North America (MoNA)LICENSEThe content of the MoNA database is licensed under CC BY 4.0.https://mona.fiehnlab.ucdavis.edu/documentation/license
- NIST Mass Spectrometry Data CenterLICENSEData covered by the Standard Reference Data Act of 1968 as amended.https://www.nist.gov/srd/public-law2-Oxazolidinethione, 5-ethenyl-http://www.nist.gov/srd/nist1a.cfm
- SpectraBase5-vinyloxazolidinethionehttps://spectrabase.com/spectrum/EHawQ8zrhaa
- Springer Nature
- Wikidata(+/-)-goitrinhttps://www.wikidata.org/wiki/Q5577929
- Wikipedia
- Wiley
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.htmlAntithyroid Agentshttps://www.ncbi.nlm.nih.gov/mesh/68013956
- NORMAN Suspect List ExchangeLICENSEData: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0https://creativecommons.org/licenses/by/4.0/NORMAN Suspect List Exchange Classificationhttps://www.norman-network.com/nds/SLE/
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 403437919https://pubchem.ncbi.nlm.nih.gov/substance/403437919
CONTENTS