Natamycin

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  • Identifiers

    CAS number
    7681-93-8

    Molecular formula
    C33H47NO13

    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

    Safety labels

  • Odor profile

    Fragrance
    Odorless 39.4%
    Spicy 30.55%
    Sweet 29.39%
    Nutty 22.48%
    Roasted 21.61%
    Caramellic 20.33%
    Coconut 19.93%
    Vanilla 19.86%
    Lactonic 18.08%
    Milky 17.45%

     

    Flavor
    Bitter 63.46%
    Fatty 22.72%
    Odorless 21.56%
    Alkaline 21.15%
    Sweet-like 20.84%
    Cauliflower 20.66%
    Cedarleaf 20.65%
    Shrimp 20.6%
    Naphthalic 20.26%
    Fenugreek 20.07%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -1.3

    pKa est.
    7.81 (neutral)

    Molecular weight
    665.7 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    4233°C

    Melting point expt.

    • 290 dec °C

    Flash point

    • 221.41 ˚C est.

    Solubility expt.

    • 4100 mg/L (at 21 °C)

  • Synonyms

    • NATAMYCIN
    • pimaricin
    • 7681-93-8
    • Myprozine
    • Pimafucin
    • Tennecetin
    • Natacyn
    • Natamicina
    • Natamycine
    • Delvocid
    • Mycophyt
    • Pimaracin
    • Synogil
    • Natamycinum
    • Antibiotic A-5283
    • Delvolan
    • Pimaricine
    • Pimarizin
    • CL 12,625
    • 8O0C852CPO
    • INS NO.235
    • INS-235
    • NSC-759167
    • CL 12625
    • CL-12625
    • DTXCID301163
    • DTXSID6021163
    • E-235
    • 16-(3-Amino-3,6-didesoxy-beta-D-mannopyranosyloxy)-5,6-epoxy-8,12,14-trihydroxy-26-methyl-2,10-dioxo-1-oxacyclohexacosa-3,17,19,21,23-pentaen-13-carbonsaeure
    • CHEBI:7488
    • (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
    • (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
    • RefChem:56874
    • DTXCID501473823
    • (1R,3S,5R,7R,12R,22R,24S,25R,26S)-22-(((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))octacosa-8,14,16,18,20-pentaene-25-carboxylic acid
    • (1R*,3S*,5R*,7R*,8E,12R*,14E,16E,18E,20E,22R*,24S*,25R*,26S*)-22-(3-Amino-3,6-dideoxy-beta-D-mannopyranosyloxy)-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
    • 231-683-5
    • 6,11,28-Trioxatricyclo(22.3.1.05,7)octacosa-8,14,16,18,20-pentaene-25-carboxylic acid, 22-((3-amino-3,6-dideoxy-beta-D-mannopyranosyl)oxy)-1,3,26-trihydroxy-12-methyl-10-oxo-, (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-
    • DTXSID201015573
    • MFCD00135085
    • Delvopos
    • Natafucin
    • Natamycin(Pimaricin)
    • C33H47NO13
    • Tymasil
    • 6,11,28-Trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid, 22-[(3-amino-3,6-dideoxy-.beta.-D-mannopyranosyl)oxy]-1,3,26-trihydroxy-12-methyl-10-oxo-, (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-
    • Pimarizin [German]
    • Natamycine [INN-French]
    • Natamycinum [INN-Latin]
    • Natamicina [INN-Spanish]
    • UNII-8O0C852CPO
    • Tennecetin;
    • Myprozine;
    • Natafucin;
    • Pimafucin;
    • Pimafugin;
    • Mycophyt;
    • Natacyn;
    • Synogil;
    • Natamycin [USAN:USP:INN:BAN]
    • NCGC00016686-01
    • (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-[(3-amino-3,6-dideoxy-beta-D-mannopyranosyl)oxy]-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.0~5,7~]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid
    • 6,11,28-TRIOXATRICYCLO(22.3.1.05,7)OCTACOSA-8,14,16,18,20-PENTAENE-25-CARBOXYLIC ACID, 22-((3-AMINO-3,6-DIDEOXY-.BETA.-D-MANNOPYRANOSYL)OXY)-1,3,26-TRIHYDROXY-12-METHYL-10-OXO-, (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-
    • CAS-7681-93-8
    • EINECS 231-683-5
    • Pimaricin; Natamycin
    • Natamycin (Standard)
    • NATAMYCIN [FCC]
    • NATAMYCIN [INN]
    • PIMARICIN [JAN]
    • NATAMYCIN [MI]
    • NATAMYCIN [USAN]
    • NATAMYCIN [VANDF]
    • NATAMYCIN [MART.]
    • NATAMYCIN [USP-RS]
    • NATAMYCIN [WHO-DD]
    • SCHEMBL18140
    • 0(5,7)]octacosa-8,14,16,18,20-pentaene-25-carboxylic ac
    • orb1310363
    • orb3025289
    • NATAMYCIN [ORANGE BOOK]
    • CHEMBL1200656
    • HY-B0133R
    • MSK2531
    • NATAMYCIN [USP MONOGRAPH]
    • NCXMLFZGDNKEPB-FFPOYIOWSA-N
    • (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-methyltetrahydro-2H-pyran-2-yl)oxy)-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.
    • (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-methyltetrahydro-2H-pyran-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
    • EX-A1989
    • HY-B0133
    • Tox21_110561
    • BDBM50370755
    • EBC-27421
    • AKOS030485970
    • 73 - Natamycin (pimaricin) in cheese
    • AN26164
    • CS-1909
    • DB00826
    • NSC 759167
    • NICOTINAMIDE_ADENINE_DINUCLEOTIDE
    • Stereoisomer of 22-((3-amino-3,6-dideoxy-beta-D-mannopyranosyl)oxy)-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo(22.3.1.0(sup 5,7))octacosa-8,14,16,18,20-pentaene-25-carboxylic acid
    • NS00003340
    • Natamycin, VETRANAL(TM), analytical standard
    • NCGC00373238-02_C33H47NO13_Delvocid
    • 681N938
    • EN300-22411493
    • Pimaricin preparation, ~2.5%, aqueous suspension
    • Q248466
    • Natamycin, United States Pharmacopeia (USP) Reference Standard
    • Pimaricin, from Streptomyces chattanoogensis, >=95% (HPLC)
    • Natamycin, Pharmaceutical Secondary Standard; Certified Reference Material
    • (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-methyl-tetrahydropyran-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
    • (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-[(3-Amino-3,6-dideoxy-|A-D-mannopyranosyl)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
    • (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]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid
    • 7681-93-8

  • Applications

    Natamycin (CAS 7681-93-8) is a polyene antifungal agent primarily used as a food preservative to control mold in dairy, cheese, meats, and fermented beverages, and it is also applied as a coating or additive in food packaging films to inhibit surface mold growth and extend shelf life; it is used as an antifungal active ingredient in pharmaceutical products, including topical formulations and ophthalmic solutions; in polymer and packaging applications, natamycin may be incorporated into coatings or films to provide antifungal protection for food-contact materials; it is also evaluated for postharvest agricultural use to protect fruits and vegetables from mold during storage, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3.86
    methanol 55.76
    isopropanol 0.45
    water 0.82
    ethyl acetate 1.4
    n-propanol 2.01
    acetone 3.36
    n-butanol 0.94
    acetonitrile 1.61
    DMF 54.25
    toluene 0.33
    isobutanol 0.64
    1,4-dioxane 5.55
    methyl acetate 2.26
    THF 8.12
    2-butanone 2.51
    n-pentanol 0.68
    sec-butanol 0.45
    n-hexane 0.02
    ethylene glycol 13.41
    NMP 68.16
    cyclohexane 0.03
    DMSO 47.95
    n-butyl acetate 0.54
    n-octanol 0.34
    chloroform 1.88
    n-propyl acetate 0.84
    acetic acid 35.89
    dichloromethane 3.27
    cyclohexanone 4.3
    propylene glycol 9.01
    isopropyl acetate 0.54
    DMAc 46.26
    2-ethoxyethanol 13.06
    isopentanol 0.44
    n-heptane 0.02
    ethyl formate 3.64
    1,2-dichloroethane 1.48
    n-hexanol 0.32
    2-methoxyethanol 36.72
    isobutyl acetate 0.38
    tetrachloromethane 0.22
    n-pentyl acetate 0.74
    transcutol 20.81
    n-heptanol 0.42
    ethylbenzene 0.12
    MIBK 0.6
    2-propoxyethanol 8.97
    tert-butanol 0.27
    MTBE 0.2
    2-butoxyethanol 5.84
    propionic acid 5.84
    o-xylene 0.2
    formic acid 120.58
    diethyl ether 0.55
    m-xylene 0.18
    p-xylene 0.13
    chlorobenzene 0.39
    dimethyl carbonate 5.34
    n-octane 0.01
    formamide 73.31
    cyclopentanone 9.27
    2-pentanone 1.39
    anisole 0.84
    cyclopentyl methyl ether 1.37
    gamma-butyrolactone 17.02
    1-methoxy-2-propanol 11.39
    pyridine 4.63
    3-pentanone 1.37
    furfural 22.65
    n-dodecane 0.01
    diethylene glycol 16.87
    diisopropyl ether 0.06
    tert-amyl alcohol 0.32
    acetylacetone 3.74
    n-hexadecane 0.01
    acetophenone 1.59
    methyl propionate 3.54
    isopentyl acetate 0.38
    trichloroethylene 4.01
    n-nonanol 0.37
    cyclohexanol 0.49
    benzyl alcohol 1.61
    2-ethylhexanol 0.18
    isooctanol 0.26
    dipropyl ether 0.47
    1,2-dichlorobenzene 0.41
    ethyl lactate 2.75
    propylene carbonate 4.76
    n-methylformamide 35.89
    2-pentanol 0.23
    n-pentane 0.02
    1-propoxy-2-propanol 3.36
    1-methoxy-2-propyl acetate 2.33
    2-(2-methoxypropoxy) propanol 5.09
    mesitylene 0.09
    ε-caprolactone 5.26
    p-cymene 0.08
    epichlorohydrin 12.2
    1,1,1-trichloroethane 0.34
    2-aminoethanol 15.33
    morpholine-4-carbaldehyde 45.58
    sulfolane 39.88
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 1.65
    n-hexyl acetate 0.83
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 7.8
    sec-butyl acetate 0.35
    tert-butyl acetate 0.51
    decalin 0.01
    glycerin 37.47
    diglyme 14.5
    acrylic acid 14.5
    isopropyl myristate 0.2
    n-butyric acid 3.83
    acetyl acetate 1.45
    di(2-ethylhexyl) phthalate 0.88
    ethyl propionate 1.02
    nitromethane 46.74
    1,2-diethoxyethane 1.51
    benzonitrile 0.83
    trioctyl phosphate 0.48
    1-bromopropane 0.32
    gamma-valerolactone 40.98
    n-decanol 0.22
    triethyl phosphate 0.63
    4-methyl-2-pentanol 0.13
    propionitrile 1.0
    vinylene carbonate 7.18
    1,1,2-trichlorotrifluoroethane 32.81
    DMS 1.39
    cumene 0.07
    2-octanol 0.14
    2-hexanone 0.8
    octyl acetate 0.47
    limonene 0.11
    1,2-dimethoxyethane 9.9
    ethyl orthosilicate 0.53
    tributyl phosphate 0.47
    diacetone alcohol 2.1
    N,N-dimethylaniline 0.62
    acrylonitrile 3.16
    aniline 0.92
    1,3-propanediol 8.1
    bromobenzene 0.28
    dibromomethane 0.96
    1,1,2,2-tetrachloroethane 2.46
    2-methyl-cyclohexyl acetate 0.64
    tetrabutyl urea 1.01
    diisobutyl methanol 0.09
    2-phenylethanol 0.84
    styrene 0.15
    dioctyl adipate 0.83
    dimethyl sulfate 13.14
    ethyl butyrate 0.73
    methyl lactate 10.33
    butyl lactate 2.17
    diethyl carbonate 0.52
    propanediol butyl ether 6.81
    triethyl orthoformate 0.78
    p-tert-butyltoluene 0.07
    methyl 4-tert-butylbenzoate 2.15
    morpholine 8.13
    tert-butylamine 0.08
    n-dodecanol 0.13
    dimethoxymethane 18.21
    ethylene carbonate 3.99
    cyrene 15.06
    2-ethoxyethyl acetate 2.77
    2-ethylhexyl acetate 0.31
    1,2,4-trichlorobenzene 0.68
    4-methylpyridine 1.99
    dibutyl ether 0.23
    2,6-dimethyl-4-heptanol 0.09
    DEF 4.76
    dimethyl isosorbide 9.42
    tetrachloroethylene 2.07
    eugenol 3.62
    triacetin 2.88
    span 80 4.08
    1,4-butanediol 3.28
    1,1-dichloroethane 0.42
    2-methyl-1-pentanol 0.41
    methyl formate 26.73
    2-methyl-1-butanol 0.58
    n-decane 0.02
    butyronitrile 0.65
    3,7-dimethyl-1-octanol 0.2
    1-chlorooctane 0.09
    1-chlorotetradecane 0.03
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.01
    cyclooctane 0.02
    cyclopentanol 0.91
    tetrahydropyran 1.34
    tert-amyl methyl ether 0.28
    2,5,8-trioxanonane 10.4
    1-hexene 0.06
    2-isopropoxyethanol 3.49
    2,2,2-trifluoroethanol 12.56
    methyl butyrate 1.56

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction