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PENICILLIC ACID

PENICILLIC ACID Structure
CAS No.
90-65-3
Chemical Name:
PENICILLIC ACID
Synonyms
NSC 402844;pencillicacid;PENICILLINACID;PENICILLIC ACID;kyselinapenicilova;PENICILLIC ACID 99%;Penicillic acid,99%;Penicillic acid, 99% 25MG;Penicillic Acid in Methanol;Benzylpenicillin Impurity 26
CBNumber:
CB0338325
Molecular Formula:
C8H10O4
Molecular Weight:
170.16
MOL File:
90-65-3.mol
MSDS File:
SDS
Modify Date:
2024/12/18 13:37:16

PENICILLIC ACID 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)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P271-P260
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.)
NFPA 704
0
1 0

PENICILLIC ACID Chemical Properties,Uses,Production

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.

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.

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.

PENICILLIC ACID Preparation Products And Raw materials

Raw materials

Preparation Products

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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% PENICILLINACID Penicillic acid from Penicillium cyclopium 3-Methoxy-5-methyl-4-oxo-2,5-hexadienoic acid, PA Penicillic acid,99% Penicillic acid3-Methoxy-5-methyl-4-oxo-2,5-hexadienoic acid Penicillic acid, 99% 25MG (E)-3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid NSC 402844 Inhibitor,Bacterial,Penicillic acid,inhibit,Caspase,Antibiotic,Apoptosis 2,5-Hexadienoic acid, 3-methoxy-5-methyl-4-oxo- Benzylpenicillin Impurity 26 Penicillic Acid in Methanol Penicillic Acid in Acetonitrile 90-65-3 antibiotic