Delvopos

Base Information Edit

Chemical Name:Delvopos
CAS No.:7681-93-8
Molecular Formula:C33H47NO13
Molecular Weight:665.735
Hs Code.:29419090
European Community (EC) Number:231-683-5
Metabolomics Workbench ID:43114
NCI Thesaurus Code:C47634
RXCUI:7268
Wikipedia:Natamycin
Mol file:7681-93-8.mol

Synonyms:Myprozine;Natamycin;Pimafucin;Pimaricin;Tennecetin

Suppliers and Price of Delvopos

Supply Marketing:Edit

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Usbiological
Natamycin
100mg
$ 425.00

TRC
Natamycin
100mg
$ 95.00

TRC
Natamycin
200mg
$ 155.00

Sigma-Aldrich
Pimaricin from
100mg
$ 820.00

Sigma-Aldrich
Pimaricin
1gm
$ 1260.00

Sigma-Aldrich
Pimaricin, Streptomyces chattanoogensis - CAS 7681-93-8 - Calbiochem
1 g
$ 1248.75

Sigma-Aldrich
Natamycin Pharmaceutical Secondary Standard; Certified Reference Material
1g
$ 129.00

Sigma-Aldrich
Natamycin VETRANAL
50mg
$ 128.00

Sigma-Aldrich
Pimaricin from
25mg
$ 245.00

Sigma-Aldrich
Pimaricin
100mg
$ 228.47

Total 207 raw suppliers

Chemical Property of Delvopos Edit

Chemical Property:

Appearance/Colour:white to off-white solid
Vapor Pressure:0mmHg at 25°C
Melting Point:2000 °C
Refractive Index:1.62
Boiling Point:952.2 °C at 760 mmHg
PKA:pKa 4.6(50% aq. MeOEtOH) (Uncertain);8.35 (Uncertain)
Flash Point:529.7 °C
PSA：230.99000
Density:1.0 g/mL at 20 °C(lit.)
LogP:0.82000
Storage Temp.:2-8°C
Sensitive.:Light Sensitive
Solubility.:Soluble in DMSO
Water Solubility.:0.41g/L(21 oC)
XLogP3:-1.3
Hydrogen Bond Donor Count:7
Hydrogen Bond Acceptor Count:14
Rotatable Bond Count:3
Exact Mass:665.30474055
Heavy Atom Count:47
Complexity:1220

Purity/Quality:

99% ^*data from raw suppliers

Natamycin ^*data from reagent suppliers

Safty Information:

Pictogram(s): Xn
Hazard Codes:Xn
Statements: 22
Safety Statements: 24/25-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

Canonical SMILES: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
Isomeric 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)OC4[C@H]([C@H]([C@@H]([C@H](O4)C)O)N)O
Recent ClinicalTrials:The Antibiogram and Outcomes of Antimicrobial Regimens in Microbial Keratitis: A Prospective Cohort Study
Description Pimaricin (also known as natamycin, INN) belongs to a naturally occurring antifungal agent produced through the fermentation of the bacterium Streptomyces natalensis. It is a kind of macrolide polyene antifungal used for the treatment of fungal keratitis, which is a kind of eye infection. In medical field, it can be used for the treatment of various kind of fungal infections caused by Candida, Aspergillus, Cephalosporium, Fusarium, and Penicillium. In food industry, it can be used as a natural preservative to prevent fungal outgrowth. Its mechanism of action is through binding to the ergosterol in the plasma membrane of fungi, inhibiting the process of ergosterol-dependent fusion of vacuoles and membrane fusion, further inhibiting the fungal growth. It also inhibit the transport of amino acid and glucose through inhibiting membrane transport proteins. Natamycin was discovered in the 1950s. As described by Struyk et al. A new crystalline antibiotic, pimaricin, has been isolated from fermentation broth of a culture of a Streptomyces species, isolated from a soil sample obtained near Pietermaritzburg, State of Natal, Union of South Africa. This organism has been named Strepyomyces natalensis. The original name "pimaracin" can be found in earlier publications but it is no longer accepted by the WHO. Natamycin is classified as a macrolide polyene antifungal and is characterized by a macrocyclic lactone-ring with a number of conjugated carbon–carbon double bonds. The full chemical name is 22-(3-amino-3,6-dideoxy-b-D-manno pyranosol) oxy- 1,3,26 trihydroxy-12-methyl-10-oxo-6,11,28-trioxiatri [22.3.1.05.7] o catosa- 8,14,16,18,20-pentanene-25-carboxylic acid. Natamycin has a low solubility in water (approximately 40 ppm), but the activity of neutral aqueous suspensions is very stable. Natamycin is stable to heat and it is reported that heating processes for several hours at 100 C lead to only slight activity losses. Natamycin is active against almost all foodborne yeasts and molds but has no effect on bacteria or viruses. The sensitivity to natamycin in vitro (minimal inhibitory concentration) is in most cases below 20 ppm. Natamycin acts by binding irreversibly with ergosterol and other sterols, which are present in the cell membranes of yeasts and vegetative mycelium of molds. It disrupts the cell membrane and increases the cell permeability, which finally leads to cell death. The fungicidal of natamycin is an ‘‘all-or-none’’ effect, which destroys the cell membrane of the target cells. Due its interaction with ergosterol, which is a major constituent of fungal cells, it is unlikely that fungi will develop resistance. So far, after many decades of use, no development of resistance has been reported. Natamycin is mostly used for surface applications, particularly for treating surfaces of hard cheese and salamitype sausages. One of the advantages over sorbate is that even the dissolved fraction of natamycin hardly migrates into the food matrix. Natamycin can be applied by spraying the surface (e.g. of cheese), by dipping, by applying natamycin via coating emulsions or by direct addition. The antifungal efficacy of natamycin has been extensively studied and a substantial amount of scientific papers have been published. Comprehensive overview articles are available. However, due to its long history of use, no data on application studies have been published recently. Natamycin is a naturally occurring macrolide polyene antifungal agent produced during fermentation by the bacterium S. natalensis, commonly found in soil. With minimal inhibitory concentrations ranging from 4-64 μM, natamycin is used to treat fungal infections, including Candida, Aspergillus, Cephalosporium, Fusarium, and Penicillium. Natamycin blocks fungal growth by binding specifically to ergosterol with an apparent affinity of ~100 μM, but it does not permeabilize cell membranes as other polyene antibiotics are known to do. Natamycin is also used in the food industry as a preservative.
Uses Natamycin (l), from Streptomyces nataIensis and Streptomyces chat tanoogensis, is used for the control of diseases of bulbs. Polyene antifungal antibiotic analgesic, antimigraine Pimaricin is a macrocyclic tetraene originally isolated from Streptomyces natalensis in 1957. Pimaricin exhibits broad spectrum antifungal activity against yeast and filamentous fungi by binding specifically to ergosterol to block fungal growth. Unlike the related polyenes, nystatin and filipin, pimaricin does not change the permeability of the plasma membrane. Pimaricin is used in the food industry for surface treatment of cheeses as a mould inhibitor. Pimaricin is a preservative for use as a coating on the surface of italian cheeses to prevent the growth of mold or yeast. It is tasteless, odorless, colorless, and does not penetrate the cheese. It is very active against virtually all molds and yeasts, but does not affect bacteria, thus not affecting the ripening and flavor improvement process of cheese. It can be applied as a dip, spray, or by other methods such as incorporation into the cheese coatings. It is used at levels ranging from 300 to 2,000 ppm.
Therapeutic Function Antibacterial (ophthalmic)
Biological Functions Natamycin, also known as pimaracin, belongs to the polyene family of antibiotics; (a group of antifungal agents which target and bind to eukaryotic sterols and specifically ergosterol), and it is a secondary metabolite of Streptomyces natalensis . Very low levels (10–20 ppm) are needed to inhibit almost all yeasts and molds, while no amount of natamycin is sufficient to inhibit most bacteria, as they lack the sterol targeted by natamycin (some gram-positive types may be susceptible). Thus, natamycin may be used to retard the growth of fungi in meat products to which fermentative cultures are added, and is typically applied as a surface treatment (i.e., dip or spray). Resistant organisms are not typically encountered even though natamycin has been used as a food preservative for more than three decades. Unlike most bacteriocins, natamycin is toxic to eukaryotes. Acceptable daily intake of natamycin for humans is 0–0.3 mg/kg of body weight.

Technology Process of Delvopos

There total 3 articles about Delvopos which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 4,5-desepoxypimaricin

: 7681-93-8
natamycin

Guidance literature:: With PimD; dihydrogen peroxide; ascorbic acid; at 25 ℃; for 0.5h; pH=7.5; aq. buffer; Enzymatic reaction;
DOI:10.1016/j.chembiol.2010.05.026