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1,3-dithiolane

Chemical Structure

General Material Information

Preferred name 1,3-dithiolane
Trivial Name 1,3-Dithiolane
Short Description 1,3-dithiacyclopentane
Formula C3 H6 S2
CAS Number 4829-04-3
FDA UNII 341G58G6YL
Nikkaji Number J91.134H
Beilstein Number 102455
MDL MFCD00041425
xLogP3-AA 1.40 (est)
Bio Activity Summary External link
NMR Predictor External link
Synonyms
  • 1,3-dithiacyclopentane
  • 1,3-Dithiacyclopentane
  • Dithiolane
  • NSC 193357

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Literature & References

1,3-dithiolane
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):20970
Pubchem (sid):134984355
Publications by PubMed
Design, synthesis, and antimelanogenic effects of (2-substituted phenyl-1,3-dithiolan-4-yl)methanol derivatives.
Indium-Catalyzed Reductive Dithioacetalization of Carboxylic Acids with Dithiols: Scope, Limitations, and Application to Oxidative Desulfurization.
Development and comparison of HPLC and MEKC methods for the analysis of cyclic sulfur mustard degradation products.
Synthesis of ferrocenyl-substituted 1,3-dithiolanes via [3 + 2]-cycloadditions of ferrocenyl hetaryl thioketones with thiocarbonyl S-methanides.
Diradical reaction mechanisms in [3 + 2]-cycloadditions of hetaryl thioketones with alkyl- or trimethylsilyl-substituted diazomethanes.
Development of a dynamic headspace gas chromatography-mass spectrometry method for on-site analysis of sulfur mustard degradation products in sediments.
Selective arylthiolane deprotection by singlet oxygen: a promising tool for sensors and prodrugs.
Cross-dehydrogenative coupling of azoles with α-C(sp3)-H of ethers and thioethers under metal-free conditions: functionalization of H-N azoles via C-H activation.
Synthesis of pyrrolidine-fused 1,3-dithiolane oligomers by the cycloaddition of polycyclic dithiolethiones to maleimides and evaluation as mercury(II) indicators.
Molecular mechanisms of (R,R)ZX-5 on NO synthesis and its anti-angiogenic effect.
1-Oxo-1,3-dithiolanes--synthesis and stereochemistry.
Cationic cyclization of 2-alkenyl-1,3-dithiolanes: diastereoselective synthesis of trans-decalins.
Structural requirements of (E)-6-benzylidene-4a-methyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one derivatives as novel melanogenesis inhibitors.
Lead detoxification activities and ADMET hepatotoxicities of a class of novel 5-(1-carbonyl-L-amino-acid)-2,2-dimethyl-[1,3]dithiolane-4-carboxylic acids.
The mechanism of (R,R) ZX-5 on increasing NO release.
A bimetallic aluminum(salen) complex for the synthesis of 1,3-oxathiolane-2-thiones and 1,3-dithiolane-2-thiones.
Diastereoselective formal total synthesis of (+/-)-triptolide via a novel cationic cyclization of 2-alkenyl-1,3-dithiolane.
Novel Cr(III) dinuclear complexes supported by salicyloylhydrazono dithiolane and dithiane ligands: synthesis, stability, crystal structures and magnetic properties.
Headspace-trap gas chromatography-mass spectrometry for determination of sulphur mustard and related compounds in soil.
Trace determination of sulphur mustard and related compounds in water by headspace-trap gas chromatography-mass spectrometry.
Synthesis, DNA intercalation and 3D QSAR analysis of cis-2,4,5-trisubstituted-1,3-dithiolanes as a novel class of antitumor agents.
1,3-Dioxolane-based ligands as rigid analogues of naftopidil: structure-affinity/activity relationships at alpha1 and 5-HT1A receptors.
Synthesis and magnetic properties of new mono- and binuclear iron complexes with salicyloylhydrazono dithiolane ligand.
Comparative molecular dynamics simulations of the potent synthetic classical cannabinoid ligand AMG3 in solution and at binding site of the CB1 and CB2 receptors.
Nucleophilic additions to alkylidene bis(sulfoxides): stereoelectronic effects in vinyl sulfoxides.
Efficient cleavage of the N-O bond of 3,6-dihydro-1,2-oxazines mediated by some alpha-hetero substituted carbonyl compounds in mild conditions.
Dinuclear Cp* cobalt complexes of the 1,2,4,5-benzenetetrathiolate bischelating ligand.
Combined 3D QSAR and molecular docking studies to reveal novel cannabinoid ligands with optimum binding activity.
Stereoelectronic effects in cyclic sulfoxides, sulfones, and sulfilimines: application of the Perlin effect to conformational analysis.
Intramolecular thia-anti-Michael addition of a sulfur anion to enones: a regiospecific approach to multisubstituted thiophene derivatives.
General strategy for the syntheses of corynanthe, tacaman, and oxindole alkaloids.
Reaction of the acetals with TESOTf-base combination; speculation of the intermediates and efficient mixed acetal formation.
Very strong ferromagnetic interaction in a new binuclear mu-methoxo-bridged Mn(III) complex: synthesis, crystal structure, magnetic properties, and DFT calculations.
Heteroatom-substituted expanded radialenes: one-pot synthesis and characterization of expanded 1,3-dithiolane[n]radialenes.
gem-Difluorination of 2,2-diaryl-1,3-dithiolanes by Selectfluor and pyridinium polyhydrogen fluoride.
Alpha-keto amide peptides: a synthetic strategy to resin-bound peptide isosteres for protease inhibitor screening on solid support.
A computational study of the cycloaddition of thiobenzophenone S-methylide to thiobenzophenone.
A new approach to the chemical synthesis of keto-proteins.
Highly diastereoselective 1,3-dipolar cycloaddition reactions of trans-2-methylene-1,3-dithiolane 1,3-dioxide with 3-oxidopyridinium and 3-oxidopyrylium betaines: a route to the tropane skeleton.
Relationship between nitric oxide production and choroidal blood flow.
Thioformaldehyde S-methylide and thioacetone S-methylide: an ab initio MO study of structure and cycloaddition reactivity.
Mechanisms controlling cell cycle arrest and induction of apoptosis after 12-lipoxygenase inhibition in prostate cancer cells.
Discovery and design of retinoic acid receptor and retinoid X receptor class- and subtype-selective synthetic analogs of all-trans-retinoic acid and 9-cis-retinoic acid.
C-H activation with elemental sulfur: synthesis of cyclic thioureas from formaldehyde aminals and S8.
Dynamic NMR studies of a potential chiroptical switch based on dithiocarbamate-iminodithiolane interconversion.
Dithiolane analogs of lignans inhibit interferon-gamma and lipopolysaccharide-induced nitric oxide production in macrophages.
Differential membrane fluidization by active and inactive cannabinoid analogues.
Palladium-catalyzed cyclization reactions of 2-vinylthiiranes with heterocumulenes. Regioselective and enantioselective formation of thiazolidine, oxathiolane, and dithiolane derivatives.
Eicosanoid regulation of angiogenesis: role of endothelial arachidonate 12-lipoxygenase.
Synthesis of 1,3-dithianes and 1,3-dithiolanes. Baker's yeast reduction and lipase-catalyzed resolution for synthesis of enantiopure derivatives.
Structure elucidation and conformational properties of synthetic cannabinoids (-)-2-(6a,7,10,10a-tetrahydro-6,6,9-trimethyl-1-hydroxy-6H-dibe nzo [b,d]pyranyl)-2-hexyl-1,3-dithiolane and its methylated analog.
Pharmacophoric requirements for cannabinoid side chains: multiple bond and C1'-substituted delta 8-tetrahydrocannabinols.
Apoptosis in the absence of cytochrome c accumulation in the cytosol.
Synthesis and evaluation of novel rhodacyanine dyes that exhibit antitumor activity.
Requirement for epidermal growth factor receptor tyrosine kinase and for 12-lipoxygenase activity in the expression of 12-lipoxygenase in human epidermoid carcinoma cells.
Critical role of arachidonate lipoxygenases in regulating apoptosis.
EGF-receptor tyrosine kinase and 12-lipoxygenase activity regulate expression of 12-lipoxygenase in human tumor cells.
Hepatotoxicity of diisopropyl ester of malonic acid and chloromalonic acids, disinfection by-products of the fungicide isoprothiolane.
Meso-2,3-dimercaptosuccinic acid mono-N-alkylamides: syntheses and biological activity as novel in vivo cadmium mobilizing agents.
Synthesis of [4,5-Bis(hydroxymethyl)-1,3-dithiolan-2-yl]nucleosides as Potential Inhibitors of HIV(1).
Plasmalogens and their oxidative degradation products in low and high density lipoprotein.
12(S)-HETE is a mitogenic factor for microvascular endothelial cells: its potential role in angiogenesis.
Enhanced endothelial cell retraction mediated by 12(S)-HETE: a proposed mechanism for the role of platelets in tumor cell metastasis.
Spectroscopic quantitation of organic isothiocyanates by cyclocondensation with vicinal dithiols.
[Studies on metabolism of fungicide benzoic acid, 1,3-dithiolan-2-ylidenehydrazide in vitro].
[Studies on metabolism of a fungicide yekuling in rat].
Metabolism of 7-(1,3-dithiolan-2-ylmethyl)-1,3-dimethylxanthine by rat liver microsomes. Diastereoselective metabolism of the 1,3-dithiolane ring.
Stereoselective S-oxygenation of 2-aryl-1,3-dithiolanes by the flavin-containing and cytochrome P-450 monooxygenases.
Enantioselective S-oxygenation of 2-aryl-1,3-dithiolanes by rabbit lung enzyme preparations.
Enantioselective S-oxygenation of para-methoxyphenyl-1,3-dithiolane by various tissue preparations: effect of estradiol.
2,3-Dithioerythritol, a possible new arsenic antidote.
Immunohistochemical study of arachidonate 12-lipoxygenase in porcine tissues.
[In vitro transformation of Syrian hamster embryo cells by four chemicals].
[Studies on toxicokinetics of 14C-Yekuling in rats after intratracheal injection].
Potential anticonvulsants. 11. Synthesis and anticonvulsant activity of spiro[1,3-dioxolane-2,3'-indolin]-2'-ones and structural analogues.
[An experimental study on the embryotoxicity and teratogenicity of a new fungicide "Yu-7802" (BHD) in mice].
[Studies on the carcinogenicity of a new fungicide, 2-benzoyl-hydrazono-1,3-dithiolane (BHD), in rats].
Potent cephalosporinase inhibitors: 7 beta-[2-(1, 3-dithiolan-2-ylidene) acetamido] cephalosporins and related compounds.
Occupational effect of phosfolan insecticide on spraymen during field exposure.
[Cyclic ketals. 10. Oxidation behavior of 2-substituted 1,3-dithiolane and 1,3-dithane].
[Thermal decomposition of cysteine, cystine, N-acetylcysteine, 4-thiazolidinecarboxylic acid and cysteine methyl ester in soy bean oil (authors transl)].
[Hydrolytic stability of various 1,3-dioxolane, 1,3-oxathiolane and 1,3-dithiolane derivatives].

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
HMDB (The Human Metabolome Database):Search
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 106.21082305908
Boiling Point 175 to 176°C @ 760 mm Hg
Vapor Pressure 1.573 mmHg @ 25 °C
Flash Point TCC Value 63.6 °C TCC
logP (o/w) 0.555 est
Solubility
alcohol Yes
water, 4063 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Sulfurous
sweet, sulfurous, onion, onion cooked onion
General comment At 0.10 % in dipropylene glycol. sweet sulfurous onion
Flavor Type: Sulfurous
sweet, sulfurous, ripe, onion
General comment Sweet sulfurous ripe onion

Potential Uses

Applications
Odor purposes Chocolate, Coffee
Flavoring purposes Garlic, Meat
Other purposes Gravies

Safety Information

Safety information

Preferred SDS: View
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50 900 mg/kg
European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 17, Pg. 235, 1982.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
information only not used for fragrances or flavors
Recommendation for 1,3-dithiolane usage levels up to:
not for fragrance use.
Recommendation for 1,3-dithiolane flavor usage levels up to:
not for flavor use.

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :20970
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
1,3-dithiolane
Chemidplus:0004829043
RTECS:JP0511000 for cas# 4829-04-3