Diallyltetrasulfid

Strukturformel
Allgemeines
Name	Diallyltetrasulfid
Summenformel	C6H10S4
Kurzbeschreibung	ölige Flüssigkeit
Externe Identifikatoren/Datenbanken
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
Siedepunkt	122 °C (16 hPa)
Löslichkeit	löslich in Dimethylformamid (30 g/l) und DMSO (30 g/l)
Sicherheitshinweise
GHS-Gefahrstoffkennzeichnung Achtung
H- und P-Sätze	H: 302
	P: 264‐270‐301+310‐330‐501
	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. In einer Studie wurde der Gehalt in diesem Öl zu 4,22 % bestimmt. Auch in weiteren Allium-Arten (vor allem deren Ölen) kommt es vor, darunter Schnittlauch, Zwiebel, Knoblauch-Schnittlauch, im Ackerlauch und zu 10,88 % im Schalottenöl.

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

Knoblauch
Schnittlauch
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.

Eigenschaften

Diallyltetrasulfid ist ein starkes Antioxidationsmittel. Es wirkt außerdem durch Bildung von Wasserstoffperoxid hämolytisch.

Dimethyltetrasulfid wirkt antimikrobiell gegen viele Arten, darunter Helicobacter pylori, Staphylococcus aureus, Flavobacterium columnare, Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumoniae, sowie Campylobacter jejuni, Bacillus cereus, Listeria monocytogenes, Salmonella enterica und Vibrio cholera.

Diallyltetrasulfid wirkt fungizid gegen mehrere Arten von Candida und Aspergillus, darunter Candida utilis.

Einzelnachweise

1 2 3 4 5 Cayman Chemical: Diallyl Tetrasulfide (ICD-1585, CAS Number: 2444-49-7), abgerufen am 28. Juli 2023
↑ Dictionary of Food Compounds with CD-ROM. CRC Press, ISBN 978-1-4200-6845-0, S. 413 (eingeschränkte Vorschau in der Google-Buchsuche).
↑ 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.
↑ 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.
1 2 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).
1 2 3 4 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.
1 2 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.
1 2 3 4 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.
↑ 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).
↑ 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.
1 2 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.
↑ 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.
1 2 3 4 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.
↑ 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.
↑ 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.
↑ 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.
1 2 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.
1 2 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.

[caymanchem.com-1] 1 2 3 4 5 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.

[:0-5] 1 2 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).

[:1-6] 1 2 3 4 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.

[:2-7] 1 2 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.

[:4-8] 1 2 3 4 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.

[:3-11] 1 2 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.

[:6-13] 1 2 3 4 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.

[:5-17] 1 2 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.

[:7-18] 1 2 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.