| Identification | Back Directory | [Name]
PENICILLIC ACID | [CAS]
90-65-3 | [Synonyms]
pencillicacid
PENICILLINACID
PENICILLIC ACID
kyselinapenicilova
Penicillic acid,99%
PENICILLIC ACID 99%
Penicillic acid, 99% 25MG
3-methoxy-5-methyl-4-oxo-5-hexadienoicacid
Penicillic acid from Penicillium cyclopium
3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid
3-METHOXY-5-METHYL-4-OXO-2,5-HEXADIENOIC ACID
3-Methoxy-5-methyl-4-oxo-2,5-hexadienoic acid, PA
Penicillic acid3-Methoxy-5-methyl-4-oxo-2,5-hexadienoic acid
gamma-keto-beta-methoxy-delta-methylene-delta(supalpha)-hexenoicacid | [EINECS(EC#)]
202-008-1 | [Molecular Formula]
C8H10O4 | [MDL Number]
MFCD00004365 | [MOL File]
90-65-3.mol | [Molecular Weight]
170.16 |
| Chemical Properties | Back Directory | [Appearance]
white to light beige crystals or powder | [Melting point ]
83-87 °C
| [Boiling point ]
219.79°C (rough estimate) | [density ]
1.1456 (rough estimate) | [refractive index ]
1.4425 (estimate) | [storage temp. ]
Store at 2-8 | [solubility ]
DMSO: >10mg/mL | [form ]
solid | [pka]
3.90±0.33(Predicted) | [color ]
Needles from pet ether or rhombic orhexagonal plates | [Merck ]
13,7163 | [CAS DataBase Reference]
90-65-3 | [IARC]
3 (Vol. 10, Sup 7) 1987 | [EPA Substance Registry System]
Penicillic acid (90-65-3) |
| Hazard Information | Back Directory | [Chemical Properties]
white to light beige crystals or powder | [Uses]
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. | [Description]
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. | [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]. | [storage]
Store at -20°C | [Purification Methods]
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. | [References]
[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. |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,T | [Risk Statements ]
36/37/38-20/21/22-22 | [Safety Statements ]
37/39-26-24/25 | [RIDADR ]
2811 | [RTECS ]
MM2625000 | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
29189900 | [Safety Profile]
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. | [Hazardous Substances Data]
90-65-3(Hazardous Substances Data) | [Toxicity]
LD50 i.p. in mice: 90.00 mg/kg (Chan et al.) |
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