3-Methoxy-5-methyl-4-oxohexa-2,5-diensure

Bezeichnung:3-Methoxy-5-methyl-4-oxohexa-2,5-diensure

CAS-Nr90-65-3

Englisch Name:PENICILLIC ACID

CBNumberCB0338325

SummenformelC8H10O4

Molgewicht170.16

MOL-Datei90-65-3.mol

Synonyma

3-Methoxy-5-methyl-4-oxohexa-2,5-diensure

3-Methoxy-5-methyl-4-oxohexa-2,5-diensure physikalisch-chemischer Eigenschaften

Schmelzpunkt	83-87 °C
Siedepunkt	219.79°C (rough estimate)
Dichte	1.1456 (rough estimate)
Brechungsindex	1.4425 (estimate)
storage temp.	Store at 2-8
Löslichkeit	DMSO: >10mg/mL
pka	3.90±0.33(Predicted)
Aggregatzustand	solid
Farbe	Needles from pet ether or rhombic orhexagonal plates
Merck	13,7163
CAS Datenbank	90-65-3
IARC	3 (Vol. 10, Sup 7) 1987
EPA chemische Informationen	Penicillic acid (90-65-3)

Sicherheit

Kennzeichnung gefährlicher	Xn,T
R-Sätze:	36/37/38-20/21/22-22
S-Sätze:	37/39-26-24/25
RIDADR	2811
RTECS-Nr.	MM2625000
HazardClass	6.1(b)
PackingGroup	III
HS Code	29189900
Giftige Stoffe Daten	90-65-3(Hazardous Substances Data)
Toxizität	LD50 i.p. in mice: 90.00 mg/kg (Chan et al.)

Gefahreninformationscode (GHS)

PENICILLIC ACID Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
R22:Gesundheitsschädlich beim Verschlucken.
S-Sätze Betriebsanweisung:
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Beschreibung
Gram negative bacteria utilize N-acylated homoserine lactones to coordinate expression of virulence in response to the density of the surrounding bacterial population in a process termed quorum sensing. By interfering with this communication and thereby disrupting virulence expression, quorum sensing inhibitors are emerging as an alternative to the conventional ways of fighting bacterial infections. Penicillic acid is a mycotoxin produced from Penicillium species identified in molds on corn and other grains. At 80 μM, penicillic acid inhibits bacterial quorum sensing communication in P. aeruginosa by selectively repressing various virulence factor and other quorum sensing-regulated genes. It has been shown to inhibit Fas-mediated apoptosis at 100-200 μM by targeting caspase-8 activity in Burkitt’s lymphoma Raji cells.
Chemische Eigenschaften
white to light beige crystals or powder
Verwenden
Gram negative bacteria utilize N-acylated homoserine lactones to coordinate expression of virulence in response to the density of the surrounding bacterial population in a process termed quorum sensing. By interfering with this communication and thereby disrupting virulence expression, quorum sensing inhibitors are emerging as an alternative to the conventional ways of fighting bacterial infections. Penicillic acid is a mycotoxin produced from Penicillium species identified in molds on corn and other grains. At 80 μM, penicillic acid inhibits bacterial quorum sensing communication in P. aeruginosa by selectively repressing various virulence factor and other quorum sensing-regulated genes. It has been shown to inhibit Fas-mediated apoptosis at 100-200 μM by targeting caspase-8 activity in Burkitt’s lymphoma Raji cells.
Verwenden
Penicillic acid can be isolated from the seed-borne fungus Aspergillus persii EML-HPB1-11 and it exhibits antibacterial activity against various plant pathogenic bacteria. This compound can be a potential lead molecule for developing synthetic agrochemicals. Penicillic acid is also used as a quorum sensing inhibitor.
Sicherheitsprofil
Poison by intravenous, subcutaneous, and intraperitoneal routes. Moderately toxic by ingestion. An experimental teratogen. Experimental reproductive effects. Questionable carcinogen with experimental neoplastigenic data. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
in vitro
the compound was active primarily against gram-negative bacteria, and it was also active against some gram-positive species. it showed limited antihelminthic properties but did affect the growth of oat seed coleoptiles by interference with the respiratory process. penicillic acid has proven to be too toxic for use in therapy [1]. penicillic acid (80 μm) inhibited bacterial quorum sensing communication in p. aeruginosa by selectively repressing various virulence factor and other quorum sensing-regulated genes [2]. in burkitt’s lymphoma raji cells, penicillic acid exihibited an inhibitory effect on fas-mediated apoptosis at 100-200 μm by targeting caspase-8 activity [3].
in vivo
the ldso (subcutaneous injection) for mice is 100 mg/kg. subcutaneous injection of 1.0 mg/dose twice weekly produced transplantable tumors after 64 weeks in all rats surviving treatment. in addition, a dose at 0.1 mg initiated tumor development [1].
läuterung methode
The lactone (furanone, anhydrous) hydrolyses to the acid (3-methoxy-4-oxo-hexa-2,5-dienoic acid, hydrate). It crystallises from water as the monohydrate (acid), or from pet ether as the anhydrous (lactone) compound. The free acid is in equilibrium with the lactone. UV: max 221nm ( 12,500) in 0.02M KOH; 228nm ( 11,500) in 0.02M HCl [Raphael J Chem Soc 1508 1948]. [Beilstein 3 II 519, 3 III 1467.] It is a possible antineoplastic.
Einzelnachweise
[1] ciegler a, detroy r w, lillehoj e b. patulin, penicillic acid, and other carcinogenic lactones[j]. microbial toxins, 1971, 6: 409-434.
[2] rasmussen t b, skindersoe m e, bjarnsholt t, et al. identity and effects of quorum-sensing inhibitors produced by penicillium species[j]. microbiology, 2005, 151(5): 1325-1340.
[3] bando m, hasegawa m, tsuboi y, et al. the mycotoxin penicillic acid inhibits fas ligand-induced apoptosis by blocking self-processing of caspase-8 in death-inducing signaling complex[j]. journal of biological chemistry, 2003, 278(8): 5786-5793.

3-Methoxy-5-methyl-4-oxohexa-2,5-diensure Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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