Diallyltetrasulfid

ölige Flüssigkeit[1]

Diallyltetrasulfid
Strukturformel
Strukturformel von Diallyltetrasulfid
Allgemeines
Name Diallyltetrasulfid
Summenformel C6H10S4
Kurzbeschreibung

ölige Flüssigkeit[1]

Externe Identifikatoren/Datenbanken
CAS-Nummer 2444-49-7
EG-Nummer 219-485-7
ECHA-InfoCard 100.017.714
PubChem 75552
ChemSpider 68077
Wikidata Q27292795
Eigenschaften
Molare Masse 210,40 g·mol−1
Aggregatzustand

flüssig[1]

Siedepunkt

122 °C (16 hPa)[2]

Löslichkeit

löslich in Dimethylformamid (30 g/l) und DMSO (30 g/l)[1]

Sicherheitshinweise
GHS-Gefahrstoffkennzeichnung[1]
Gefahrensymbol

Achtung

H- und P-Sätze H: 302
P: 264​‐​270​‐​301+310​‐​330​‐​501[1]
Wenn nicht anders vermerkt, gelten die angegebenen Daten bei Standardbedingungen (0 °C, 1000 hPa).

Diallyltetrasulfid ist eine chemische Verbindung aus der Gruppe der organischen Polysulfide.

Vorkommen

Diallyltetrasulfid kommt insbesondere in Knoblauchöl vor.[3][4][5][6][7][8] In einer Studie wurde der Gehalt in diesem Öl zu 4,22 % bestimmt.[9] Auch in weiteren Allium-Arten (vor allem deren Ölen) kommt es vor, darunter Schnittlauch[10], Zwiebel[6], Knoblauch-Schnittlauch[11], im Ackerlauch[12] und zu 10,88 % im Schalottenöl[13].

Das ätherische Öl von Mansoa alliacea besteht fast vollständig aus Diallyldisulfid, Diallyltrisulfid und Diallyltetrasulfid.[14]

  • Knoblauch
    Knoblauch
  • Schnittlauch
    Schnittlauch
  • Mansoa alliacea
    Mansoa alliacea

Synthese

Umsetzung von Schwefel und Natriumsulfid mit Allylbromid und Tetrabutylammoniumbromid ergibt eine Mischung aus Diallyltrisulfid, Diallyltetrasulfid, Diallylpentasulfid und Diallylhexasulfid, die anschließend getrennt werden kann.[15]

Eigenschaften

Diallyltetrasulfid ist ein starkes Antioxidationsmittel.[7] Es wirkt außerdem durch Bildung von Wasserstoffperoxid hämolytisch.[16]

Dimethyltetrasulfid wirkt antimikrobiell gegen viele Arten, darunter Helicobacter pylori[5], Staphylococcus aureus[6][8][17][13], Flavobacterium columnare[11], Pseudomonas aeruginosa[8][18], Escherichia coli[8][13], Klebsiella pneumoniae[18], sowie Campylobacter jejuni, Bacillus cereus, Listeria monocytogenes, Salmonella enterica und Vibrio cholera.[13]

Diallyltetrasulfid wirkt fungizid gegen mehrere Arten von Candida und Aspergillus[17], darunter Candida utilis.[6]

Einzelnachweise

  1. ↑ a b c d e Cayman Chemical: Diallyl Tetrasulfide (ICD-1585, CAS Number: 2444-49-7), abgerufen am 28. Juli 2023
  2. ↑ Dictionary of Food Compounds with CD-ROM. CRC Press, ISBN 978-1-4200-6845-0, S. 413 (eingeschränkte Vorschau in der Google-Buchsuche).
  3. ↑ A. Sendl: Allium sativum and Allium ursinum: Part 1 Chemistry, analysis, history, botany. In: Phytomedicine. Band 1, Nr. 4, April 1995, S. 323–339, doi:10.1016/S0944-7113(11)80011-5.
  4. ↑ Larry Lawson, Zhen-Yu Wang, Bronwyn Hughes: Identification and HPLC Quantitation of the Sulfides and Dialk(en)yl Thiosulfinates in Commercial Garlic Products. In: Planta Medica. Band 57, Nr. 04, August 1991, S. 363–370, doi:10.1055/s-2006-960119.
  5. ↑ a b E. A. O’Gara, D. J. Hill, D. J. Maslin: Activities of Garlic Oil, Garlic Powder, and Their Diallyl Constituents against Helicobacter pylori. In: Applied and Environmental Microbiology. Band 66, Nr. 5, Mai 2000, S. 2269–2273, doi:10.1128/AEM.66.5.2269-2273.2000, PMID 10788416, PMC 101489 (freier Volltext).
  6. ↑ a b c d Kim, Jay Wook et al. "Antimicrobial activity of alk (en) yl sulfides found in essential oils of garlic and onion." Food Science and Biotechnology 13.2 (2004): 235-239.
  7. ↑ a b Toshiharu Horie, Shoji Awazu, Yoichi Itakura, Toru Fuwa: Identified Diallyl Polysulfides from an Aged Garlic Extract which Protects the Membranes from Lipid Peroxidation. In: Planta Medica. Band 58, Nr. 05, Oktober 1992, S. 468–469, doi:10.1055/s-2006-961517.
  8. ↑ a b c d Sergio Casella, Michele Leonardi, Bernardo Melai, Filippo Fratini, Luisa Pistelli: The Role of Diallyl Sulfides and Dipropyl Sulfides in the In Vitro Antimicrobial Activity of the Essential Oil of Garlic, Allium sativum L., and Leek, Allium porrum L.: SULFIDES AND ANTIBACTERIAL ACTIVITY RELATIONS IN LEEK. In: Phytotherapy Research. Band 27, Nr. 3, März 2013, S. 380–383, doi:10.1002/ptr.4725.
  9. ↑ Florentine Marie-Chantal Ndoye Foe, Tatiana Flore Kemegni Tchinang, Ascencion Maximilienne Nyegue, Jean-Pierre Abdou, Abel Joel Gbaweng Yaya, Alembert Tiabou Tchinda, Jean-Louis Oyono Essame, François-Xavier Etoa: Chemical composition, in vitro antioxidant and anti-inflammatory properties of essential oils of four dietary and medicinal plants from Cameroon. In: BMC Complementary and Alternative Medicine. Band 16, Nr. 1, Dezember 2016, doi:10.1186/s12906-016-1096-y, PMID 27056828, PMC 4823886 (freier Volltext).
  10. ↑ Pongsak Rattanachaikunsopon, Parichat Phumkhachorn: Diallyl Sulfide Content and Antimicrobial Activity against Food-Borne Pathogenic Bacteria of Chives (Allium schoenoprasum). In: Bioscience, Biotechnology, and Biochemistry. Band 72, Nr. 11, 23. November 2008, S. 2987–2991, doi:10.1271/bbb.80482.
  11. ↑ a b Pongsak Rattanachaikunsopon, Parichat Phumkhachorn: Potential of Chinese chive oil as a natural antimicrobial for controlling Flavobacterium columnare infection in Nile tilapia Oreochromis niloticus. In: Fisheries Science. Band 75, Nr. 6, November 2009, S. 1431–1437, doi:10.1007/s12562-009-0171-4.
  12. ↑ Pongsak Rattanachaikunsopon, Parichat Phumkhachorn: Potential of Chinese chive oil as a natural antimicrobial for controlling Flavobacterium columnare infection in Nile tilapia Oreochromis niloticus. In: Fisheries Science. Band 75, Nr. 6, November 2009, S. 1431–1437, doi:10.1007/s12562-009-0171-4.
  13. ↑ a b c d Pongsak Rattanachaikunsopon, Parichat Phumkhachorn: Diallyl Sulfide Content and Antimicrobial Activity against Food-Borne Pathogenic Bacteria of Chives (Allium schoenoprasum). In: Bioscience, Biotechnology, and Biochemistry. Band 72, Nr. 11, 23. November 2008, S. 2987–2991, doi:10.1271/bbb.80482.
  14. ↑ M. Apparao, A. Kjær, J.ø. Madsen, E. Venkata Rao: Diallyl di-, tri- and tetrasulphide from Adenocalymma alliaceae. In: Phytochemistry. Band 17, Nr. 9, Januar 1978, S. 1660–1661, doi:10.1016/S0031-9422(00)94664-8.
  15. ↑ Alastair Baker, Michael Graz, Robert Saunders, Gareth J. S. Evans, Sandra Kaul, Thomas Wirth: Flow Synthesis of Symmetrical Di- and Trisulfides Using Phase-Transfer Catalysis. In: Journal of Flow Chemistry. Band 3, Nr. 4, 13. Dezember 2013, S. 118–121, doi:10.1556/JFC-D-13-00013.
  16. ↑ Rex Munday, John S. Munday, Christine M. Munday: Comparative effects of mono-, di-, tri-, and tetrasulfides derived from plants of the Allium family: redox cycling in vitro and hemolytic activity and Phase 2 enzyme induction in vivo. In: Free Radical Biology and Medicine. Band 34, Nr. 9, Mai 2003, S. 1200–1211, doi:10.1016/S0891-5849(03)00144-8.
  17. ↑ a b Shyh-Ming Tsao, Mei-Chin Yin: In-vitro antimicrobial activity of four diallyl sulphides occurring naturally in garlic and Chinese leek oils. In: Journal of Medical Microbiology. Band 50, Nr. 7, 1. Juli 2001, S. 646–649, doi:10.1099/0022-1317-50-7-646.
  18. ↑ a b S.-m. Tsao, M.-c. Yin: In vitro activity of garlic oil and four diallyl sulphides against antibiotic-resistant Pseudomonas aeruginosa and Klebsiella pneumoniae. In: Journal of Antimicrobial Chemotherapy. Band 47, Nr. 5, 1. Mai 2001, S. 665–670, doi:10.1093/jac/47.5.665.

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