Natamycine - ≥95%(HPLC) , Ergosterol sequestering agent, CAS No.7681-93-8, Ergosterol sequestering agent

CAS: 7681-93-8 Cat. No.: P107822 Formule: C₃₃H₄₇NO₁₃ Poids moléculaire: 665.73 Beilstein Registry Number: 1614878 Numéro CE: 231-683-5

GRADE & PURITY ≥95%(HPLC)

Synonyms

CL 12,625 | Natafucin | pimaricin | HY-B0133 | UNII-8O0C852CPO | (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-{[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.0,5,7

Storage

A conserver entre 2 et 8°C

Shipped In

Glace humide

Vue d’ensemble

La natamycine (pimaricine) est un macrolide polyénique antifongique qui se lie aux stérols de la membrane cellulaire. La natamycine (pimaricine) est un polyène macrolide antifongique qui se lie aux stérols de la membrane cellulaire. Cible : Antifongique La natamycine (INN), également connue sous le nom de pimaricine et parfois vendue sous le nom de Natacyn, est un agent antifongique naturel produit pendant la fermentation par la bactérie Streptomyces natalensis, que l'on trouve généralement dans le sol. La natamycine est très peu soluble dans l'eau, mais elle est efficace à des concentrations très faibles. La CMI (concentration minimale inhibitrice) est inférieure à 10 ppm pour la plupart des moisissures. La natamycine est classée parmi les antifongiques polyènes macrolides et, en tant que médicament, elle est utilisée pour traiter les kératites fongiques. Elle est particulièrement efficace contre les infections cornéennes à Aspergillus et Fusarium. D'autres membres courants de la famille des antifongiques polyènes macrolides sont l'amphotéricine B, la nystatine et la filipine. La natamycine est également utilisée dans l'industrie alimentaire comme conservateur naturel. La natamycine est utilisée pour traiter les infections fongiques, y compris le Candida, l'Aspergillus, le Cephalosporium, le Fusarium et le Penicillium. Elle est appliquée sous forme de crème, de gouttes oculaires ou (pour les infections orales) de pastilles. La natamycine présente une absorption négligeable dans l'organisme lorsqu'elle est administrée de ces manières. Lorsqu'elle est prise par voie orale, elle est peu ou pas absorbée par le tractus gastro-intestinal, ce qui la rend inappropriée pour les infections systémiques.

Specifications

Synonymes

CL 12,625 | Natafucin | pimaricin | HY-B0133 | UNII-8O0C852CPO | (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-{[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.0,5,7

Spécifications et pureté

≥95%(HPLC)

Mécanismes biochimiques et physiologiques

Macrolide polyénique antifongique qui se lie spécifiquement à l'ergostérol et bloque la croissance fongique. Cependant, contrairement à la nysatine et à la filipine, la pimaricine ne modifie pas la perméabilité de la membrane plasmique. Inhibiteur de la s

Conditions de stockage de stockage

A conserver entre 2 et 8°C

Expédié en

Glace humide

Type d'action

SEQUESTERING AGENT

Mécanisme d'action

Ergosterol sequestering agent

Note

Dans la mesure du possible, les solutions doivent être préparées et utilisées le même jour. Toutefois, si vous devez préparer des solutions de base à l'avance, nous vous recommandons de les conserver sous forme d'aliquotes dans des flacons hermétiques à -20°C. Ces aliquotes sont généralement utilisables pendant un mois. En général, ces solutions peuvent être utilisées pendant un mois. Avant utilisation, et avant d'ouvrir le flacon, nous vous recommandons de laisser votre produit s'équilibrer à température ambiante pendant au moins 1 heure. Besoin de plus de conseils sur la solubilité, l'utilisation et la manipulation ? Veuillez consulter notre page de questions fréquemment posées (FAQ) pour plus de détails.

Pureté

≥95%(HPLC)

Noms et identifiants

• Pubchem Sid: 488195286
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488195286
• Sourires canoniques: CC1CC=CC=CC=CC=CC(CC2C(C(CC(O2)(CC(CC3C(O3)C=CC(=O)O1)O)O)O)C(=O)O)OC4C(C(C(C(O4)C)O)N)O
• IUPAC Name: (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid
• InChIKey: NCXMLFZGDNKEPB-FFPOYIOWSA-N
• INCHI: 1S/C33H47NO13/c1-18-10-8-6-4-3-5-7-9-11-21(45-32-30(39)28(34)29(38)19(2)44-32)15-25-27(31(40)41)22(36)17-33(42,47-25)16-20(35)14-24-23(46-24)12-13-26(37)43-18/h3-9,11-13,18-25,27-30,32,35-36,38-39,42H,10,14-17,34H2,1-2H3,(H,40,41)/b4-3+,7-5+,8-6+,11-9+,13-12+/t18-,19-,20+,21+,22+,23-,24-,25+,27-,28+,29-,30+,32+,33-/m1/s1
• Isomères SMILES: C[C@@H]1C/C=C/C=C/C=C/C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H](C[C@@H]3[C@H](O3)/C=C/C(=O)O1)O)O)O)C(=O)O)O[C@H]4[C@H]([C@H]([C@@H]([C@H](O4)C)O)N)O
• WGK Allemagne: 3
• RTECS: TK3325000
• Poids moléculaire: 665.73
• Beilstein: 1614878
• Reaxy-Rn: 25144604
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25144604&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Classe Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Aminosaccharides
          • Level6 Aminoglycosides

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Aminosaccharides
• Direct Parent: Aminoglycosides
• Alternative Parents: Macrolides and analogues Hexoses O-glycosyl compounds Beta hydroxy acids and derivatives Oxanes Dicarboxylic acids and derivatives Enoate esters Amino acids 1,2-aminoalcohols Lactones Hemiacetals Secondary alcohols Oxacyclic compounds Acetals Carboxylic acids Dialkyl ethers Polyols Epoxides Organic oxides Monoalkylamines Carbonyl compounds Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Aminoglycoside core - Macrolide - Hexose monosaccharide - O-glycosyl compound - Glycosyl compound - Beta-hydroxy acid - Hydroxy acid - Monosaccharide - Dicarboxylic acid or derivatives - Oxane - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Hemiacetal - Secondary alcohol - Carboxylic acid ester - Amino acid - Amino acid or derivatives - 1,2-aminoalcohol - Lactone - Acetal - Carboxylic acid derivative - Oxacycle - Carboxylic acid - Dialkyl ether - Organoheterocyclic compound - Oxirane - Ether - Polyol - Alcohol - Organic nitrogen compound - Amine - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Primary amine - Carbonyl group - Organonitrogen compound - Primary aliphatic amine - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

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PDE5A Tclin Phosphodiesterase 5A (5113 Activities)

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EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)

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CA2 Tclin Carbonic anhydrase II (17698 Activities)

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ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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HMGCR Tclin HMG-CoA reductase (2475 Activities)

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NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

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INSR Tclin Insulin receptor (5558 Activities)

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PGR Tclin Progesterone receptor (8562 Activities)

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ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

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CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)

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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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ACE Tclin Angiotensin-converting enzyme (1423 Activities)

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DRD2 Tclin Dopamine D2 receptor (23596 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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DRD4 Tchem Dopamine D4 receptor (7907 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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HRH2 Tclin Histamine H2 receptor (5428 Activities)

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ADRA1D Tclin Alpha-1d adrenergic receptor (4171 Activities)

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HTR1B Tclin Serotonin 1b (5-HT1b) receptor (2801 Activities)

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HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

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HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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CALCR Tclin Calcitonin receptor (2215 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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HRH1 Tclin Histamine H1 receptor (7573 Activities)

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ADRA1B Tclin Alpha-1b adrenergic receptor (2912 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)

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OPRD1 Tclin Delta opioid receptor (15096 Activities)

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OPRK1 Tclin Kappa opioid receptor (16155 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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HTR4 Tclin Serotonin 4 (5-HT4) receptor (2068 Activities)

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ESR2 Tclin Estrogen receptor beta (9272 Activities)

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CYSLTR1 Tclin Cysteinyl leukotriene receptor 1 (2118 Activities)

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ERBB2 Tclin Receptor protein-tyrosine kinase erbB-2 (7851 Activities)

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CHRM4 Tclin Muscarinic acetylcholine receptor M4 (6041 Activities)

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CHRM5 Tclin Muscarinic acetylcholine receptor M5 (4677 Activities)

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ADRA2B Tclin Alpha-2b adrenergic receptor (4412 Activities)

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Agtr2 Angiotensin II type 2 (AT-2) receptor (803 Activities)

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Mc4r Melanocortin receptor 4 (1205 Activities)

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Ltc4s Leukotriene C4 synthase (1 Activities)

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Sigmar1 Sigma opioid receptor (160 Activities)

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Npy1r Neuropeptide Y receptor type 1 (8 Activities)

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Cckar Cholecystokinin A receptor (90 Activities)

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Nos2 Nitric oxide synthase, inducible (3573 Activities)

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Mapk1 MAP kinase ERK2 (650 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Mmp9 Matrix metalloproteinase 9 (38 Activities)

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Microsporum canis (872 Activities)

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Aspergillus flavus (8875 Activities)

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Aspergillus niger (16508 Activities)

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Aspergillus sp. (177 Activities)

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Aspergillus oryzae (433 Activities)

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Aspergillus wentii (9 Activities)

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Aspergillus fumigatus (16427 Activities)

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Candida albicans (78123 Activities)

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Fusarium oxysporum (3998 Activities)

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Trichophyton rubrum (3646 Activities)

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Aspergillus ochraceus (560 Activities)

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Fusarium verticillioides (912 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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BCHE Cholinesterase (8742 Activities)

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Alternaria alternata (757 Activities)

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Fusarium avenaceum (92 Activities)

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Fusarium sp. (88 Activities)

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Aspergillus versicolor (452 Activities)

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Glra2 Glycine receptor (1745 Activities)

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Aspergillus brasiliensis (162 Activities)

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Mécanismes d'action

Propriétés chimiques et physiques

• Solubilité: ≥16.425mg/mL in DMSO with gentle warming,insoluble in EtOH,insoluble in H2O
• Point d'éclair (°C): >110°C
• Point d'ébullition (°C): 952°C
• Point de fusion (°C): 280°C（分解）
• Poids moléculaire: 665.700 g/mol
• XLogP3: -1.300
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 3
• Exact Mass: 665.305 Da
• Monoisotopic Mass: 665.305 Da
• Topological Polar Surface Area: 231.000 Ų
• Heavy Atom Count: 47
• Formal Charge: 0
• Complexity: 1220.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 14
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 5
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 5
• Covalently-Bonded Unit Count: 1

Références

1. Chaoyi Shen, Xiangzheng Yang, Da Wang, Jiangkuo Li, Changqing Zhu, Di Wu, Kunsong Chen.  (2023)  Carboxymethyl chitosan and polycaprolactone-based rapid in-situ packaging for fruit preservation by solution blow spinning.  CARBOHYDRATE POLYMERS,      [PMID:38142080] [10.1016/j.carbpol.2023.121636]

2. Xiangzheng Yang, Jingshan Rao, Chaoyi Shen, Huan Lian, Da Wang, Di Wu, Kunsong Chen.  (2023)  Natamycin-Loaded Ethyl Cellulose/PVP Films Developed by Microfluidic Spinning for Active Packaging.  Foods,  13  (1): (132).  [PMID:38201160] [10.3390/foods13010132]

3. Yuxuan Cao, Xu Zhang, Xiaoning Song, Wenkui Li, Zheng Ren, Juntao Feng, Zhiqing Ma, Xili Liu, Yong Wang.  (2023)  Efficacy and toxic action of the natural product natamycin against Sclerotinia sclerotiorum.  PEST MANAGEMENT SCIENCE,      [PMID:38087429] [10.1002/ps.7930]

4. Mengying Sun, Jiang Yu, Yinglong Song, Xinling Li, Guangqing Mu, Yanfeng Tuo.  (2023)  Fermented milk by Lactobacillus delbrueckii, Lacticaseibacillus paracasei, and Kluyveromyces marxianus shows special physicochemical and aroma formation during the storage.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2023.103025]

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Foire aux questions

What is the purity of this product, and how is it determined?

This product is supplied at ≥95% purity, determined by HPLC. Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at 2–8 °C. Refrigerated storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships chilled on wet ice. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 7681-93-8, the molecular formula is C33H47NO13, and the molecular weight is 665.73 g/mol. InChIKey NCXMLFZGDNKEPB-FFPOYIOWSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.