Basic information Safety Supplier Related
ChemicalBook >  Product Catalog >  Chemical Reagents >  Organic reagents >  fatty acid >  PENICILLIC ACID

PENICILLIC ACID

Basic information Safety Supplier Related

PENICILLIC ACID Basic information

Product Name:
PENICILLIC ACID
Synonyms:
  • 3-METHOXY-5-METHYL-4-OXO-2,5-HEXADIENOIC ACID
  • 3-methoxy-5-methyl-4-oxo-5-hexadienoicacid
  • gamma-keto-beta-methoxy-delta-methylene-delta(supalpha)-hexenoicacid
  • kyselinapenicilova
  • pencillicacid
  • PENICILLIC ACID
  • 3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid
  • PENICILLIC ACID 99%
CAS:
90-65-3
MF:
C8H10O4
MW:
170.16
EINECS:
202-008-1
Product Categories:
  • antibiotic
Mol File:
90-65-3.mol
More
Less

PENICILLIC ACID Chemical Properties

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
pka
3.90±0.33(Predicted)
form 
solid
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)
More
Less

Safety Information

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
Hazardous Substances Data
90-65-3(Hazardous Substances Data)
Toxicity
LD50 i.p. in mice: 90.00 mg/kg (Chan et al.)

MSDS

  • Language:English Provider:ACROS
More
Less

PENICILLIC ACID Usage And Synthesis

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.

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.

Uses

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.

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.

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].

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.

PENICILLIC ACIDSupplier

J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Email
jkinfo@jkchemical.com
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
4006608290; 18621169109
Email
market03@meryer.com
BOC Sciences
Tel
1-631-485-4226; 16314854226
Email
info@bocsci.com
Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725
Email
waley188@sohu.com
Beijing innoChem Science & Technology Co.,Ltd.
Tel
400-810-7969 010-59572699
Email
ningzi.li@inno-chem.com.cn