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natamycin
myprozine

Supplier Sponsors

CAS Number: 7681-93-8Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:231-683-5
FDA UNII: 8O0C852CPO
MDL:MFCD00135085
XlogP3-AA:-1.30 (est)
Molecular Weight:665.73419000
Formula:C33 H47 N O13
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:fungicidal preservatives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 FDA/DG SANTE Petitions, Reviews, Notices:
EU SANCO Natamycin View - review
GRN 517 Natamycin View - notice PDF
GRN 578 Natamycin View - notice PDF
JECFA Food Additive: Natamycin
GSFA Codex: Natamycin (Pimaricin) (235)
DG SANTE Food Additives:natamycin
FDA Mainterm (SATF):7681-93-8 ; NATAMYCIN
FDA Regulation:
FDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION
Subpart B--Food Preservatives
Sec. 172.155 Natamycin (pimaricin).
 
Physical Properties:
Appearance:white crystalline powder (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Specific Gravity:1.02000 @ 25.00 °C.
Melting Point: 290.00 °C. @ 760.00 mm Hg
Boiling Point: 952.17 °C. @ 760.00 mm Hg (est)
Flash Point: 985.00 °F. TCC ( 529.70 °C. ) (est)
logP (o/w): 0.880 (est)
Soluble in:
 water, 4100 mg/L @ 21C (exp)
 methanol, slightly
 acetic acid
 dimethyl formamide
Insoluble in:
 water
 mineral oil
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
American International Chemical, LLC.
NATAMYCIN
Anhui Haibei
Pimafucin (Pimaricin in a 2.5% sterile water suspension)
BOC Sciences
For experimental / research use only.
Pimaricin
Foodchem International
Natamycin
Glentham Life Sciences
Pimaricin
Graham Chemical
Natamycin
Jiangyin Healthway
Natamycin
New functional food ingredients
Sigma-Aldrich: Sigma
For experimental / research use only.
Pimaricin from Streptomyces chattanoogensis, ≥95% (HPLC)
Sinofi Food Ingredients
Natamycin
Odor: characteristic
Use: Preservative, Cosmetics, Feed, Pharmaceutical, Fungicide, Mold Inhibitor, Antimicrobial, Antifungal, Antibacterial, Cheese, Cookie, Salad Dressing, Soft Drink, Jams, Jellies, Pickled food, Meat, Margarine, Fruit Juice, Sauces, Baking Food, Sauage, Yoghourt, Beer, Wine, Flavoring Agent.
Tianjin Talent Chemical
Natamycin
United International
Natamycin Nat.
United International
Natamycin Nat.
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 2730 mg/kg
Toxicology and Applied Pharmacology. Vol. 8, Pg. 97, 1966.

intramuscular-cat LD50 90 mg/kg
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.

intraperitoneal-cat LD50 75 mg/kg
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.

oral-cat LD50 > 300 mg/kg
Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.

intravenous-dog LD50 18 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.

oral-dog LD50 > 300 mg/kg
Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.

intramuscular-guinea pig LD50 130 mg/kg
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.

intraperitoneal-guinea pig LD50 90 mg/kg
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.

oral-guinea pig LD50 450 mg/kg
Antibiotics Annual. Vol. 5, Pg. 878, 1957/1958.

intravenous-mammal (species unspecified) LD30 500 mg/kg
"Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 2, Pg. 954, 1978.

intraperitoneal-mouse LD50 40 mg/kg
Quarterly Journal of Crude Drug Research. Vol. 8, Pg. 1274, 1968.

intravenous-mouse LD50 > 5000 mg/kg
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 16, Pg. 1461, 1985.

oral-mouse LD50 1500 mg/kg
"Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 517, 1967.

intramuscular-rabbit LD50 120 mg/kg
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.

intraperitoneal-rabbit LD50 68 mg/kg
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.

intravenous-rabbit LD50 20 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.

oral-rabbit LD50 1420 mg/kg
GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Toxicology and Applied Pharmacology. Vol. 8, Pg. 97, 1966.

intramuscular-rat LD50 128 mg/kg
BEHAVIORAL: TOLERANCE
Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.

intraperitoneal-rat LD50 85 mg/kg
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.

intravenous-rat LD50 36 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.

Dermal Toxicity:
subcutaneous-rat LD50 190 mg/kg
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.

subcutaneous-guinea pig LD50 160 mg/kg
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.

subcutaneous-mouse LD50 180 mg/kg
"Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 639, 1967.

subcutaneous-rabbit LD50 180 mg/kg
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
fungicidal preservatives
Recommendation for natamycin usage levels up to:
 not for fragrance use.
 
Recommendation for natamycin flavor usage levels up to:
 not for flavor use.
 
Safety References:
European Food Safety Authority (EFSA) reference(s):

Scientific Opinion on the use of natamycin (E 235) as a food additive
View page or View pdf

EPI System: View
ClinicalTrials.gov:search
Daily Med:search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
Carcinogenic Potency Database:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :6433509
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
Chemidplus:0007681938
RTECS:TK3325000 for cas# 7681-93-8
 
References:
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):6433509
Pubchem (sid):134988703
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
KEGG (GenomeNet):C08073
HMDB (The Human Metabolome Database):HMDB14964
FooDB:FDB002337
Export Tariff Code:2941.90.5000
FDA Listing of Food Additive Status:View
MedlinePlusSupp:View
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
 antibiotic A-5283
 delvocid
 mycophyt
 myprozine
 natacyn
 pimafucin
 pimaricin
 pimaricine
 tennecetin
 

Articles:

Info:EVALUATION OF CERTAIN FOOD ADDITIVES AND CONTAMINANTS
PubMed:Improvement of ε-poly-L-lysine production through seed stage development based on in situ pH monitoring.
PubMed:Natamycin content and quality evaluation of yoghurt from small- and large-scale brands in Turkey.
PubMed:In vitro drug release of natamycin from β-cyclodextrin and 2-hydroxypropyl-β-cyclodextrin-functionalized contact lens materials.
PubMed:Natamycin based sol-gel antimicrobial coatings on polylactic acid films for food packaging.
PubMed:Antifungal agents against Aspergillus niger for rearing rice leaffolder larvae (Lepidoptera: Pyralidae) on artificial diet.
PubMed:Interaction of gelatin with polyenes modulates antifungal activity and biocompatibility of electrospun fiber mats.
PubMed:Effect of natamycin, nisin and glycerol on the physicochemical properties, roughness and hydrophobicity of tapioca starch edible films.
PubMed:Yeasts are essential for cocoa bean fermentation.
PubMed:Functional properties and antifungal activity of films based on gliadins containing cinnamaldehyde and natamycin.
PubMed:SlnM gene overexpression with different promoters on natamycin production in Streptomyces lydicus A02.
PubMed:Efficacy of nisin and/or natamycin to improve the shelf-life of Galotyri cheese.
PubMed:Citrus extract or natamycin treatments on "Tzatziki" - a traditional Greek salad.
PubMed:Effect of natamycin on cytochrome P450 enzymes in rats.
PubMed:Survey of South African fruit juices using a fast screening HILIC-MS method.
PubMed:Influence of fungal elicitors on biosynthesis of natamycin by Streptomyces natalensis HW-2.
PubMed:Physicochemical responses and microbial characteristics of shiitake mushroom (Lentinus edodes) to gum arabic coating enriched with natamycin during storage.
PubMed:Shelf-life evaluation of natural antimicrobials for Concord and Niagara grape juices.
PubMed:Multi-detection of preservatives in cheeses by liquid chromatography-tandem mass spectrometry.
PubMed:Evaluation of antimicrobial edible coatings from a whey protein isolate base to improve the shelf life of cheese.
PubMed:Use of poly(N-isopropylacrylamide) nanohydrogels for the controlled release of pimaricin in active packaging.
PubMed:Genome shuffling of Streptomyces gilvosporeus for improving natamycin production.
PubMed:Novel natural food antimicrobials.
PubMed:Growth/no growth interfaces of table olive related yeasts for natamycin, citric acid and sodium chloride.
PubMed:Effect of natamycin in combination with pure oxygen treatment on postharvest quality and selected enzyme activities of button mushroom (Agaricus bisporus).
PubMed:[Analytical method for natamycin in wine using high-performance liquid chromatography].
PubMed:A novel and rapid method for determination of natamycin in wines based on ultrahigh-performance liquid chromatography coupled to tandem mass spectrometry: validation according to the 2002/657/EC European decision.
PubMed:Development of an RP-HPLC method for the simultaneous determination of benzoic acid, sorbic acid, natamycin and lysozyme in hard and pasta filata cheeses.
PubMed:Efficacy of natamycin to control fungal growth in natural black olive fermentation.
PubMed:In vitro antifungal effect of black cumin seed quinones against dairy spoilage yeasts at different acidity levels.
PubMed:Anti-yeast activity of a food-grade dilution-stable microemulsion.
PubMed:PEF based hurdle strategy to control Pichia fermentans, Listeria innocua and Escherichia coli k12 in orange juice.
PubMed:Chromosome aberrations, micronucleus and sperm head abnormalities in mice treated with natamycin, [corrected] a food preservative.
PubMed:Enzymology of the polyenes pimaricin and candicidin biosynthesis.
PubMed:The polyene antimycotics nystatin and filipin disrupt the plasma membrane, whereas natamycin inhibits endocytosis in germinating conidia of Penicillium discolor.
PubMed:Identification of an antifungal metabolite produced by a potential biocontrol Actinomyces strain A01.
PubMed:Natamycin production by Streptomyces gilvosporeus based on statistical optimization.
PubMed:Effects of cultivation conditions on the production of natamycin with Streptomyces gilvosporeus LK-196.
PubMed:Efficacy of natamycin for control of growth and ochratoxin A production by Aspergillus carbonarius strains under different environmental conditions.
PubMed:Combinations of antimycotics to inhibit the growth of molds capable of producing 1,3-pentadiene.
PubMed:Evaluation of certain food additives and contaminants.
PubMed:Growth of Mycobacterium avium subsp. paratuberculosis in the presence of hexadecylpyridinium chloride, natamycin, and vancomycin.
PubMed:Cloning and in vivo functional analysis by disruption of a gene encoding the gamma-butyrolactone autoregulator receptor from Streptomyces natalensis.
PubMed:Stability of natamycin and its cyclodextrin inclusion complexes in aqueous solution.
PubMed:Formation of natamycin:cyclodextrin inclusion complexes and their characterization.
PubMed:Comparative study of a semisynthetic derivative of natamycin and the parent antibiotic on the spoilage of shredded cheddar cheese.
PubMed:Evaluation of certain food additives and contaminants.
PubMed:Characterization and control of thread mould in cheese.
PubMed:A complex multienzyme system encoded by five polyketide synthase genes is involved in the biosynthesis of the 26-membered polyene macrolide pimaricin in Streptomyces natalensis.
PubMed:[Determination of natamycin residues in ripening cheeses by high-performance liquid chromatography].
PubMed:Rapid spectrophotometric method for analyzing natamycin in cheese and cheese rind.
PubMed:Growth and aflatoxin production by Aspergillus parasiticus in a medium at different pH values and with or without pimaricin.
PubMed:Effects of fungicide treatment and vacuuming on pyroglyphid mites and their allergens in mattress dust.
PubMed:Control of house-dust mites (Pyroglyphidae) with home disinfectants.
PubMed:Effects of natamycin and potassium sorbate on growth and aflatoxin production in olives.
PubMed:[Determining natamycin residues in maturing cheeses].
PubMed:Prevention of surface mold growth on Italian dry sausage by natamycin and potassium sorbate.
PubMed:Natamycin approved--first U.S. drug for fungal keratitis.
PubMed:Editorial: The FDA and ophthalmic therapeutics.
PubMed:Pimaricin and mycostatin for retarding cottage cheese spoilage.
PubMed:Effect of hamycin on plasma cholesterol of rat.
PubMed:Acute and chronic toxicity of pimaricin.
 
Notes:
amphoteric macrolide antifungal antibiotic from streptomyces natalensis or s. chattanoogensis. it is used for a variety of fungal infections, mainly topically. Primarily used as a surface treatment to prevent growth of yeasts and moulds, esp. on cheese. Permitted agent in USA for surface treatment of cheeses as mould-inhibitor. No reported allergic reactions and it has GRAS status Natamycin (INN), also known as pimaricin, is a naturally occurring antifungal agent produced during fermentation by the bacterium Streptomyces natalensis, commonly found in soil. Natamycin has a very low solubility in water, due to the amphiphilic nature of the molecule. However, natamycin is effective at very low levels. Most Molds have an MIC (Minimum inhibitory concentration) of <10ppm. Natamycin is classified as a macrolide polyene antifungal and, as a drug, is used to treat fungal keratitis. It is especially effective against Aspergillus and Fusarium corneal infections. Other common members of the polyene macrolide antifungal family are Amphotericin B, Nystatin, and Filipin.; Natamycin is an antifungal drug for topical ophthalmic administration. It is a tetraene polyene antibiotic derived from Streptomyces natalensis. It possesses in vitro activity against a variety of yeast and filamentous fungi, including Candida, Aspergillus, Cephalosporium, Fusarium and Penicillium. Although the activity against fungi is dose-related, natamycin is predominantly fungicidal. Natamycin is not effective in vitro against gram-positive or gram-negative bacteria. Topical administration appears to produce effective concentrations of natamycin within the corneal stroma but not in intraocular fluid.
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