Penicillic acid

170.163

170.16

202-008-1

DTXSID1074830

NEEDLES FROM PETROLEUM ETHER

2918990090

63.60000

0.84

1.2±0.1 g/cm3

83-84 °C

285.7±35.0 °C at 760 mmHg

113.5±19.4 °C

1.482

MODERATELY SOLUBLE IN COLD WATER (2 G/100 ML); FREELY SOLUBLE IN HOT WATER, ALCOHOL, ETHER, BENZENE, CHLOROFORM; SLIGHTLY SOLUBLE IN HOT PETROLEUM ETHER; PRACTICALLY INSOLUBLE IN PENTANE-HEXANE

LD50 i.p. in mice: 90.00 mg/kg (Chan et al.)

ACID REACTION, TURNS CONGO RED PAPER BLUE

PENICILLIC ACID CAN OCCUR AS KETO FORM OR LACTONE FORM|LARGE TRANSPARENT MONOCLINIC OR TRICLINIC, RHOMBIC CRYSTALS FROM WATER /MONOHYDRATE/

III

6.1(b)

UN 2811

R36/37/38

S26;S37/S39

MM2625000

Xn: Harmful;T: Toxic;

HAYES AW; MYCO TOXINS A REVIEW OF BIOLOGICAL EFFECTS AND THEIR ROLE IN HUMAN DISEASES; CLIN TOXICOL 17(1) 45 (1980). A REVIEW OF BIOLOGICAL EFFECTS OF MYCOTOXINS AND THEIR ROLE IN HUMAN DISEASES.|CHAN PK ET AL; HEPATOTOXICITY OF THE MYCOTOXIN PENICILLIC ACID: A PHARMACOKINETICS CONSIDERATION; J AM OIL CHEM SOC 58(12) 1017A (1981). A REVIEW WITH 23 REFERENCES ON PENICILLIC ACID HEPATOTOXICITY.|CARLTON WW; PENICILLIC ACID, CITRININ AND XANTHOMEGNIN QUINONE METABOLITES. A REVIEW; FOOD DRUG ADM, BUR VET MED (TECH REP) FDA/BVM (US) ISS FDA/BVM-80/132, CONF MYCOTOXINS ANIM FEEDS GRAINS RELAT ANIM HEALTH; PB80-221773: 233 (1980). A REVIEW WITH 38 REFERENCES ON PENICILLIC ACID METABOLITES.

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 39 companies from 1 notifications to the ECHA C&L Inventory.

PENICILLIC ACID AND OCHRATOXIN A ARE SYNERGISTIC TOXIC FUNGAL METABOLITES. THE EFFECT OF PENICILLIC ACID ON THE PANCREATIC ENZYME CARBOXYPEPTIDASE A IN VITRO WAS DECREASED CONVERSION OF PARENT OCHRATOXIN A TO ALPHA-OCHRATOXIN, A NON-TOXIC METABOLITE. IN VIVO, PENICILLIC ACID INHIBITED MOUSE AND CHICKEN PANCREATIC CARBOXYPEPTIDASE A AFTER MULTIPLE ORAL EXPOSURE. THE MODE OF TOXIC INTERACTION OF THE 2 MYCOTOXINS MAY HAVE BEEN DUE TO IMPAIRED DETOXIFICATION OF OCHRATOXIN A THROUGH PENICILLIC ACID DEPLETION OF CARBOXYPEPTIDASE A ACTIVITY.|ACUTE CYTOTOXICITY OF PENICILLIC ACID IN MICE WAS INCREASED BY PENTOBARBITAL AND 3-METHYLCHOLANTHRENE PRETREATMENT BUT DECREASED BY SKF-525A. CYSTEINE, WHEN GIVEN 5 MINUTES BEFORE BUT NOT 20 MINUTES AFTER PENICILLIC ACID ADMINISTRATION, PROTECTED THE MICE AGAINST TOXICITY, WHILE DIETHYL MALEATE PRETREATMENT INCREASED PENICILLIC ACID TOXICITY IN THE MOUSE.

ANTIBIOTIC SUBSTANCE PRODUCED BY THE FOLLOWING FUNGI: PENICILLIUM PUBERULUM, P CYCLOPIUM, P THOMII, P SUAVEOLENS, P BAARNENSE, ASPERGILLUS OCHRACEUS, A MELLEUS. ISOLATION.|PENICILLIC ACID CAN BE PRODUCED IN CORN INFECTED WITH PENICILLIUM MARTENSII, IN MOLDY CORN, AND IN POULTRY FEED. STORAGE OF CORN INFECTED WITH P MARTENSII AT LOW TEMPERATURES AND HIGH MOISTURE LEVELS MAY INCREASE THE AMOUNT OF TOXIN PRODUCED. NO PENICILLIC ACID WAS DETECTED IN MOLD-FERMENTED SAUSAGE (SALAMI), BUT SINCE IT REACTS READILY WITH AMINO ACIDS IT MAY NOT HAVE BEEN DETECTED BY THE METHOD USED. PENICILLIC ACID WAS PRESENT IN 7 OF 20 COMMERCIAL CORN SAMPLES ANALYZED, AT LEVELS RANGING FROM 5-230 UG/KG, AND IN 5 OF 20 SAMPLES OF COMMERCIAL DRIED BEANS AT LEVELS FROM 11-179 UG/KG.

PENICILLIC ACID WAS PRESENT IN 7 OF 20 COMMERCIAL CORN SAMPLES ANALYZED, AT LEVELS RANGING FROM 5-230 UG/KG, AND IN 5 OF 20 SAMPLES OF COMMERCIAL DRIED BEANS AT LEVELS FROM 11-179 UG/KG.

...PENICILLIC ACID IS PRODUCED BY SEVERAL COMMON MOLDS OCCURRING ON FOODSTUFFS...

IN VIVO AND IN VITRO STUDIES SHOWED SIGNIFICANT UPTAKE OF (14)C-PENICILLIC ACID BY RED BLOOD CELLS AND A SIGNIFICANT INCREASE IN RADIOACTIVITY ASSOCIATED WITH THE MEMBRANE FRACTION WITH TIME (1-4 HOURS). HOWEVER, THE MAJORITY OF THE BLOOD CELL ACTIVITY WAS INTRACELLULAR. THE (14)C-RADIOACTIVITY CONCENTRATION IN LIVER FRACTIONS (1.5% OF THE RNA-DNA AND PROTEIN FRACTIONS. THE LEVEL OF THE (14)C ACTIVITY ASSOCIATED WITH THESE FRACTIONS INCREASED WITH TIME (24 HR). STUDIES OF THE IN VIVO METABOLISM OF [(14)C] PENICILLIC ACID BY RATS SHOWED THAT A SIGNIFICANT AMOUNT OF RADIOACTIVITY WAS EXCRETED IN THE URINE (82% OF THE ADMINISTERED DOSE AFTER 7 DAYS). BILIARY METABOLITES ACCOUNTED FOR 10% OF ADMINISTERED DOSE 2 HOURS AFTER ADMINISTRATION.

PENICILLIC ACID IS A KNOWN METABOLITE OF STRAINS OF PENICILLIUM ROQUEFORTI ASSOCIATED WITH BLUE-VEINED CHEESES.|TEN PERCENT OF PENICILLIC ACID METABOLITES IN MALE MICE WERE DETECTED AS GLUCURONIDE CONJUGATES. ALL METABOLITES IN URINE, PLASMA AND BILE WERE MORE POLAR THAN THE PARENT COMPOUND. THE MAJOR METABOLITES WERE CONJUGATES OR DERIVATIVES OF GLUTATHIONE OR CYSTEINE.|IN SUBCELLULAR FRACTIONS OF MOUSE LIVER HOMOGENATES, PENICILLIC ACID REACTS WITH GLUTATHIONE BOTH ENZYMICALLY AND NONENZYMICALLY; EACH REACTION WAS OF EQUAL IMPORTANCE. METABOLISM BY VARIOUS HEPATIC SUBCELLULAR FRACTIONS WAS ESSENTIALLY NONENZYMIC WHEN GLUTATHIONE WAS ABSENT, BUT METABOLISM WAS INCREASED WHEN GLUTATHIONE WAS AVAILABLE. IN THE PRESENCE OF GLUTATHIONE, 75% OF ADDED PENICILLIC ACID WAS BIOTRANSFORMED WITHIN 30 MINUTES TO METABOLITES NOT EXTRACTABLE WITH ORGANIC SOLVENTS AND MORE POLAR THAN PENICILLIC ACID.

HAS CARCINOGENIC ACTIVITY ATTRIBUTABLE TO ALPHA,BETA-UNSATURATION TOGETHER WITH AN EXTERNAL CONJUGATED DOUBLE BOND ATTACHED TO THE 4 POSITION OF THE GAMMA LACTONE RING...|The effect of penicillic acid on isolated frog's heart has been studied along with ions of Na(+), K(+), and Ca(2+). Penicillic acid has been found to inhibit the entry of these ions into cardiac tissue thereby arresting the action of the heart. The blockage can be washed away by perfusion with Ringer's solution.

THE FACTS THAT PENICILLIC ACID IS PRODUCED BY SEVERAL COMMON MOLDS OCCURRING ON FOODSTUFFS AND IS A REPORTED CARCINOGEN PLACE IT HIGH ON THE AGENDA OF POTENTIALLY IMPORTANT MYCOTOXINS.

ITS ANTIBIOTIC PROPERTIES AGAINST GRAM-POSITIVE BACTERIA ARE MUCH WEAKER THAN THOSE OF PENICILLIN, BUT IT IS MORE ACTIVE THAN PENICILLIN AGAINST GRAM-NEGATIVE ORGANISMS. IT IS ONLY WEAKLY FUNGISTATIC. NO EVIDENCE WAS FOUND THAT THIS CHEMICAL HAS EVER BEEN PRODUCED COMMERCIALLY.|THE INACTIVATION (DETOXIFICATION) OF MYCOTOXINS BY COMPONENTS OF THE SUBSTRATE HAS BEEN DEMONSTRATED FOR...PENICILLIC ACID BY AMINO ACIDS OF MEAT PRODUCTS. ...SULFHYDRYLAMINO ACIDS REACT WITH AND THUS INACTIVATE...PENICILLIC ACID. ...SEVERAL AMINO ACIDS NORMALLY OCCURRING IN MEAT (CYSTEINE, GLUTATHIONE, ARGININE, HISTIDINE, AND LYSINE) WERE CAPABLE OF READILY REACTING WITH PENICILLIC ACID. THE ADDUCTS FORMED BY THE REACTION BETWEEN CYSTEINE OR GLUTATHIONE WITH PENICILLIC ACID WERE IDENTIFIED AND FOUND TO BE NON-TOXIC TO MICE, QUAIL, AND IN THE RABBIT SKIN TEST BUT EXHIBITED TOXICITY TO THE CHICK EMBRYO. ... WHETHER...PENICILLIC ACID /IS/...NOT PRODUCED IN MEAT OR WHETHER.../IT IS/ PRODUCED BUT UNDERGO/ES/ A REACTION WITH AMINO ACIDS IS STILL UNCERTAIN.

...A FLUORIMETRIC METHOD WHICH IS SENSITIVE TO ABOUT 1-9 UG AND IS SUITABLE FOR /DETECTION OF PENICILLIC ACID IN MOST FOODSTUFFS/.|...A GAS-CHROMATOGRAPHIC METHOD OF ANALYSIS ENABLING THE SIMULTANEOUS DETERMINATION OF VERY SMALL AMOUNTS (1 UG/100 UG OF EXTRACT) OF BOTH PENICILLIC ACID AND PATULIN IN /FOODSTUFFS/.|A GAS-LIQUID CHROMATOGRAPHIC METHOD FOR THE DETECTION OF PENICILLIC ACID IN CORN, DRIED BEANS AND APPLE JUICE, WITH A LIMIT OF DETECTION OF 4 UG/KG... .|AN IMPROVED SEPARATION OF MYCOTOXINS (INCLUDING PENICILLIC ACID) FROM A COMPLICATED MATRIX (IE REFUSE-DERIVED FUEL) RESULTS BY SIMULTANEOUSLY USING SIZE EXCLUSION AND LIQUID-LIQUID PARTITIONING.

HPLC ANALYSIS OF PENICILLIC ACID IN RAT PLASMA, URINE, AND BILE.