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diphenyl disulfide

Chemical Structure

General Material Information

Preferred name diphenyl disulfide
Trivial Name Diphenyl disulfide
Short Description phenyl disulfide
Formula C12 H10 S2
CAS Number 882-33-7
FEMA Number 3225
Flavis Number 12.043
ECHA Number 212-926-4
FDA UNII 7P54H519IJ
Nikkaji Number J2.117B
Beilstein Number 639794
MDL MFCD00003065
COE Number 11757
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 578 phenyl disulfide
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 882-33-7 ; PHENYL DISULFIDE
Synonyms
  • biphenyl disulfide
  • 1,2-diphenyldisulfane
  • 1,1'- disulfanediyldibenzene
  • disulfide diphenyl
  • disulfide, diphenyl
  • 1,1'- dithiodibenzene
  • phenyl disulfide
  • phenyl disulphide
  • phenyl dithiobenzene
  • phenyldisulfanylbenzene
  • phenyldisulfide
  • phenyldithiobenzene
  • Diphenyl disulphide
  • NSC 2689
  • DPDS
  • 1,2-Diphenyldisulfane
  • (Phenyldisulfanyl)benzene
  • 1,1′-Dithiodibenzene

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

phenyldisulfanylbenzene
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:882-33-7
Pubchem (cid):13436
Pubchem (sid):134978939
Publications by US Patents
3,952,024 - Furfurylthioacetone
3,931,166 - Certain 2,5-dimethyl-3-thiopyrazines
3,968,264 - Flavoring agent
Publications by PubMed
Formation pathway of Roussin's red ester (RRE) via the reaction of a {Fe(NO)2}(10) dinitrosyliron complex (DNIC) and thiol: facile synthetic route for synthesizing cysteine-containing DNIC.
Synthesis, guest-binding, and reduction-responsive degradation properties of water-soluble cyclophanes having disulfide moieties.
Inhibition of biofilm formation, quorum sensing and infection in Pseudomonas aeruginosa by natural products-inspired organosulfur compounds.
Deprotonative metalation of aromatic compounds by using an amino-based lithium cuprate.
Sulfur-substituted tetrahedranes.
Synthesis of stable silicon heterocycles by reaction of organic substrates with a chlorosilylene [PhC(NtBu)2SiCl].
Functional groups and sulfur K-edge XANES spectra: divalent sulfur and disulfides.
Cesium carbonate-catalyzed alpha-phenylchalcogenation of carbonyl compounds with diphenyl dichalcogenide.
Heterolytic cleavage of disulfides by frustrated Lewis pairs.
Reductive addition of the benzenethiyl radical to alkynes by amine-mediated single electron transfer reaction to diphenyl disulfide.
Photosensitized oxidation of alkyl phenyl sulfoxides. C-S bond cleavage in alkyl phenyl sulfoxide radical cations.
Antioxidant activity of the new thiosulfinate derivative, S-benzyl phenylmethanethiosulfinate, from Petiveria alliacea L.
Raman spectroscopy of benzenethiolates on nanometer-scale gold clusters.
Mononitrosyl tris(thiolate) iron complex [Fe(NO)(SPh)3]- and dinitrosyl iron complex [(EtS)2Fe(NO)2]-: formation pathway of dinitrosyl iron complexes (DNICs) from nitrosylation of biomimetic rubredoxin [Fe(SR)4]2-/1- (R = Ph, Et).
Temporary anion states and dissociative electron attachment in diphenyl disulfide.
Disulfidation of alkynes and alkenes with gallium trichloride.
The reaction of allyl and benzylarsonic acids with thiols: mechanistic aspects and implications for dioxygen activation by trivalent arsenic compounds.
Capillary electrophoresis with laser induced-fluorescence detection of profens derivatized with the water-soluble fluorogenic reagent 4-N-(4-N'-aminoethyl)piperazino-7-nitro-2,1,3-benzoxadiazole.
Organochalcogens effects on delta-aminolevulinate dehydratase activity from human erythrocytic cells in vitro.
Rhodium-catalyzed disulfide exchange reaction.
Preparation of tri- and difluoromethylsilanes via an unusual magnesium metal-mediated reductive tri- and difluoromethylation of chlorosilanes using tri- and difluoromethyl sulfides, sulfoxides, and sulfones.
Diazenecarboxamide UP-91, a potential anticancer agent, acts by reducing cellular glutathione content.
Antioxidant properties of new chalcogenides against lipid peroxidation in rat brain.
Oxygen transfer reactions. 4. Reaction of high valent oxoruthenium compounds with sulfides.
Diphenyl disulfide and sodium in NMP as an efficient protocol for in situ generation of thiophenolate anion: selective deprotection of aryl alkyl ethers and alkyl/aryl esters under nonhydrolytic conditions.
Solid state optical activity of dichalcogenides: isolation by chiral crystallization and determination of absolute configuration.
Synthesis, structure, and reactions of (acylimino)triaryl-lambda(5)-bismuthanes: first comparative study of the (acylimino)pnictorane series.
Highly Selective Thioselenation of Vinylcyclopropanes with a (PhS)(2)-(PhSe)(2) Binary System and Its Application to Thiotelluration.
Co-oxidation of 2,2,5,7,8-pentamethyl-6-chromanol and diphenyl disulfide with 3-chloroperoxybenzoic acid.
Glutathione peroxidase-like antioxidant activity of diaryl diselenides: a mechanistic study.
Screening of organosulfur compounds as inhibitors of human CYP2A6.
Comparative Behavior of Aromatic Disulfide and Diselenide Monolayers on Polycrystalline Gold Films Using Cyclic Voltammetry, STM, and Quartz Crystal Microbalance.
The fate of diphenyl sulphide, diphenyl sulphoxide and diphenyl sulphone in the rat.
Effect of Co-Adsorbed Surfactant on the Structure of Self-Assembled Monolayer of Thiol on Polycrystalline Gold.
Suppressing effects of S-methyl methanethiosulfonate and diphenyl disulfide on mitomycin C-induced somatic mutation and recombination in Drosophila melanogaster and micronuclei in mice.
Suppression of aflatoxin B1- or methyl methanesulfonate-induced chromosome aberrations in rat bone marrow cells after treatment with S-methyl methanethiosulfonate.
Thiol oxidation by 1,2,3-oxadiazolinium ions, presumed carcinogens.
Catalytic effects of glutathione peroxidase mimetics on the thiol reduction of cytochrome c.
Phenylselenenyl- and phenylthio-substituted pyrimidines as inhibitors of dihydrouracil dehydrogenase and uridine phosphorylase.
Degradation of organic sulfur compounds by a coal-solubilizing fungus.
Synthesis of L-gulose, L-galactose, and their acetylated aldehydo forms from 6-S-phenyl-6-thio-D-hexoses.
Diphenyldisulfide inhibits indomethacin-induced ulcerogenesis in rats.
Molecular modeling and enzyme kinetics indicate a novel mechanism for mammalian 5-lipoxygenase.
Inhibition of mammalian 5-lipoxygenase by aromatic disulfides.
Pyrrolopyrimidine nucleosides. 18. Synthesis and chemotherapeutic activity of 4-amino-7-(3-deoxy-beta-D-ribofuranosyl)pyrrolo[2,3-d] pyrimidine-5-carboxamide (3'-deoxysangivamycin) and 4-amino-7-(2-deoxy-beta-D-ribofuranosyl)pyrrolo[2,3-d] pyrimidine-5-carboxamide (2'-deoxysangivamycin).
Movement and metabolism of S-benzyl O,O-diisopropyl phosphorothiolate (Kitazin P) and O-ethyl S,S-diphenyl phosphorodithiolate (edifenphos) in various types of soils.
Letter: Silyl phosphites. I. The reaction of silyl phosphites with diphenyl disulfide. Synthesis of S-phenyl nucleoside phosphorothioates.
[The diamides of phenyl-dithiobenzene-2,2', -3,3'- and 4,4'-disulfonic acids].

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
FDA Substances Added to Food (formerly EAFUS):View
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB31823
FooDB:FDB008501
Export Tariff Code:2930.90.2900
ChemSpider:View
Wikipedia:View
FAO:Phenyl disulfide

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 218.34170532227
Melting Point 59 to 62°C @ 760 mm Hg
Vapor Pressure 0.001 mmHg @ 25 °C
Vapor Density 7.53
Flash Point TCC Value 177.78 °C TCC
logP (o/w) 4.41
Solubility
alcohol Yes
ether Yes
water, 6.019 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Sulfurous
sulfurous, earthy, burnt
General comment At 0.10 % in propylene glycol. sulfurous earthy burnt
Flavor Type: Sulfurous
sulfurous, earthy
General comment Sulfurous earthy

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
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 100 mg/kg
National Technical Information Service. Vol. AD277-689

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavoring agents
Recommendation for diphenyl disulfide usage levels up to:
not for fragrance use.
Maximised Survey-derived Daily Intakes (MSDI-EU): ND (μg/capita/day)
Structure Class: III
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 4
Click here to view publication 4
average usual ppmaverage maximum ppm
baked goods: --
beverages(nonalcoholic): -1.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -1.00000
fruit ices: -1.00000
gelatins / puddings: -1.00000
granulated sugar: --
gravies: --
hard candy: -1.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 8 (FGE.08)[1]: Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical group 20
View page or View pdf

Flavouring Group Evaluation 74 (FGE.74)[1]: Consideration of Simple Aliphatic Sulphides and Thiols evaluated by JECFA (61st meeting) Structurally related to Aliphatic and Alicyclic Mono-, Di-, Tri-, and Polysulphides with or without Additional Oxygenated Functional Groups from Chemical Group 20 evaluated by EFSA in FGE.08 (2008)
View page or View pdf

Flavouring Group Evaluation 8, Revision 1 (FGE.08Rev1): Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical groups 20 and 30
View page or View pdf

Flavouring Group Evaluation 91 (FGE.91): Consideration of simple aliphatic and aromatic sulphides and thiols evaluated by JECFA (53rd and 68th meetings) structurally related to aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups evaluated by EFSA in FGE.08Rev1 (2009)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 8, Revision 3 (FGE.08Rev3): Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical groups 20 and 30
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 08, Revision 4 (FGE.08Rev4): Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical groups 20 and 30
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):882-33-7
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :13436
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
phenyldisulfanylbenzene
Chemidplus:0000882337
RTECS:SS6825000 for cas# 882-33-7