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Pimaricin
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Name

Pimaricin

 EINECS 231-683-5
CAS No. 7681-93-8 Density 1.0 g/mL at 20 °C(lit.)
PSA 230.99000 LogP 0.82000
Solubility 0.41g/L(21 oC) Melting Point 2000 °C
Formula C33H47NO13 Boiling Point 952.2 °C at 760 mmHg
Molecular Weight 665.735 Flash Point 529.7 °C
Transport Information N/A Appearance white to off-white solid
Safety 24/25-36 Risk Codes 22
Molecular Structure Molecular Structure of 7681-93-8 (Pimaricin) Hazard Symbols HarmfulXn
Synonyms

6,11,28-Trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylicacid, 22-[(3-amino-3,6-dideoxy-b-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)-;6,11,28-Trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylicacid, 22-[(3-amino-3,6-dideoxy-b-D-mannopyranosyl)oxy]-1,3,26-trihydroxy-12-methyl-10-oxo-,[1R-(1R*,3S*,5R*,7R*,8E,12R*,14E,16E,18E,20E,22R*,24S*,25R*,26S*)]-;Pimaricin(6CI,8CI);Tennecetin (7CI);6,11,28-Trioxatricyclo[22.3.1.05,7]octacosane,pimaricin deriv.;Antibiotic A 5283;CL 12625;Delvocid;E 235;Mycophyt;Myprozine;Myuprozine;Natacyn;Natajen;Natamax;Natamax SF;Natamax lactose;Natamycin;Pimafucin;Synogil;[1R-(1R*,3S*,5R*,7R*,8E,12R*,14E,16E,18E,20E,22R*,24S*,25R*,26S*)]-22-[(3-Amino-3,6-dideoxy-b-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-carboxylicacid;d-Natamycin;

Article Data 12

Pimaricin Synthetic route

127-09-3

sodium acetate

A

85496-13-5

AB-400

B

7681-93-8

natamycin

Conditions
ConditionsYield
With Streptomyces sp. RGU5.3 Product distribution / selectivity; Microbiological reaction; Enzymatic reaction;
42752-07-8, 54-17-1, 492-61-5, 492-62-6, 492-66-0, 530-25-6, 530-26-7, 530-27-8, 530-28-9, 552-76-1, 579-36-2, 643-69-6, 655-45-8, 2280-44-6, 3646-73-9, 7282-78-2, 7282-79-3, 7282-80-6, 7282-81-7, 7282-82-8, 7283-02-5, 7283-08-1, 7283-09-2, 7283-10-5, 7283-11-6, 7296-15-3, 7296-64-2, 7322-31-8, 10257-28-0, 12772-65-5, 12773-29-4, 12773-31-8, 12773-32-9, 12773-33-0, 12773-34-1, 19982-85-5, 28538-24-1, 32445-46-8, 32445-47-9, 32445-51-5, 32445-52-6, 34685-56-8, 34685-57-9, 35810-56-1, 39281-65-7, 39281-66-8, 39281-67-9, 39281-68-0, 39281-69-1, 39392-61-5, 39392-62-6, 39392-63-7, 39392-65-9, 39392-66-0, 39392-69-3, 40825-84-1, 40825-86-3, 40825-87-4, 40825-89-6, 42789-83-3, 46032-76-2, 54808-89-8, 66069-07-6, 120442-57-1, 120442-58-2, 120442-59-3, 120442-67-3, 131064-91-0, 131064-92-1, 131065-00-4, 131065-01-5, 131348-38-4

glucose

A

85496-13-5

AB-400

B

7681-93-8

natamycin

Conditions
ConditionsYield
With Streptomyces sp. RGU5.3 Product distribution / selectivity; Microbiological reaction; Enzymatic reaction;

4,5-desepoxypimaricin

7681-93-8

natamycin

Conditions
ConditionsYield
With PimD; dihydrogen peroxide; ascorbic acid at 25℃; for 0.5h; pH=7.5; aq. buffer; Enzymatic reaction;
7681-93-8

natamycin

1122-91-4

4-bromo-benzaldehyde

762-04-9

phosphonic acid diethyl ester

3'-N-[(4-bromophenyl)(diethoxyphosphinoyl)methyl]pimaricin

Conditions
ConditionsYield
Stage #1: natamycin; 4-bromo-benzaldehyde With triethylamine In N,N-dimethyl-formamide at 40℃; for 3h;
Stage #2: phosphonic acid diethyl ester In N,N-dimethyl-formamide at 40℃; Kabachnik-Fields Reaction;		85%
4712-55-4

diphenyl hydrogen phosphite

7681-93-8

natamycin

1122-91-4

4-bromo-benzaldehyde

3'-N-[(4-bromophenyl)(diphenoxyphosphinoyl)methyl]pimaricin

Conditions
ConditionsYield
Stage #1: natamycin; 4-bromo-benzaldehyde With triethylamine In N,N-dimethyl-formamide at 40℃; for 3h;
Stage #2: diphenyl hydrogen phosphite In N,N-dimethyl-formamide at 40℃; Kabachnik-Fields Reaction;		83%
7681-93-8

natamycin

1122-91-4

4-bromo-benzaldehyde

868-85-9

Dimethyl phosphite

3'-N-[(4-bromophenyl)(dimethoxyphosphinoyl)methyl]pimaricin

Conditions
ConditionsYield
Stage #1: natamycin; 4-bromo-benzaldehyde With triethylamine In N,N-dimethyl-formamide at 40℃; for 3h; Kabachnik-Fields Reaction;
Stage #2: Dimethyl phosphite In N,N-dimethyl-formamide at 40℃;		82%
1809-19-4

dibutyl hydrogen phosphite

7681-93-8

natamycin

1122-91-4

4-bromo-benzaldehyde

3'-N-[(4-bromophenyl)(dibutoxyphosphinoyl)methyl]pimaricin

Conditions
ConditionsYield
Stage #1: natamycin; 4-bromo-benzaldehyde With triethylamine In N,N-dimethyl-formamide at 40℃; for 3h;
Stage #2: dibutyl hydrogen phosphite In N,N-dimethyl-formamide at 40℃; Kabachnik-Fields Reaction;		81%
3663-52-3

bis(trimethylsilyl) phosphonate

7681-93-8

natamycin

1122-91-4

4-bromo-benzaldehyde

3'-N-{[bis(trimethylsilyloxy)phosphinoyl](4-bromophenyl)methyl}pimaricin

Conditions
ConditionsYield
Stage #1: natamycin; 4-bromo-benzaldehyde With triethylamine In N,N-dimethyl-formamide at 40℃; for 3h;
Stage #2: bis(trimethylsilyl) phosphonate In N,N-dimethyl-formamide at 40℃; Kabachnik-Fields Reaction;		80%

C37H34BF3N4O2

7681-93-8

natamycin

C70H80BF2N5O15

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 40℃;80%
7681-93-8

natamycin

459-57-4

4-fluorobenzaldehyde

1108187-85-4

N-(α-hydrophosphoryl-4-fluorobenzyl)pimaricin

Conditions
ConditionsYield
Stage #1: natamycin; 4-fluorobenzaldehyde With triethylamine In dimethyl sulfoxide at 40℃; for 3h;
Stage #2: With hypophosphorous acid In dimethyl sulfoxide at 30 - 35℃; Further stages.;		75%

Pimaricin Chemical Properties

Molecular Formula: C33H47NO13
Molecular Weight: 665.73  g/mol
Melting point: 2000 °C 
Form: aqueous suspension
Storage temp.:  2-8 °C
EINECS: 231-683-5
Merck: 13,6453 
Flash Point: 529.7 °C 
Index of Refraction: 1.62
Surface Tension: 71 dyne/cm
Density: 1.0 g/mL at 20 °C(lit.)
Vapour Pressure: 0 mmHg at 25 °C
Enthalpy of Vaporization: 157.21 kJ/mol
Boiling Point: 952.2 °C at 760 mmHg 
Following is the Structure of  Pimaricin (CAS NO.7681-93-8):

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](CC2[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
InChI: 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
InChIKey: NCXMLFZGDNKEPB-RXKQOUODSA-N

Pimaricin Uses

 Pimaricin (CAS NO.7681-93-8) is commonly used as polyene antifungal antibiotic.It is used to treat fungal infections, including Candida, Aspergillus, Cephalosporium, Fusarium and Penicillium.In the food industry,it's used as a hurdle to fungal outgrowth in dairy products, meats, and other foods.

Pimaricin Toxicity Data With Reference

1.    

orl-rat LD50:2730 mg/kg

     TXAPA9    Toxicology and Applied Pharmacology. 8 (1966),97.
2.    

ipr-rat LD50:85 mg/kg

     ANTCAO    Antibiotics and Chemotherapy. 9 (1959),406.
3.    

scu-rat LD50:190 mg/kg

     ANTCAO    Antibiotics and Chemotherapy. 9 (1959),406.
4.    

ivn-rat LD50:36 mg/kg

     ANTCAO    Antibiotics and Chemotherapy. 9 (1959),406.
5.    

ims-rat LD50:128 mg/kg

     ANTCAO    Antibiotics and Chemotherapy. 9 (1959),406.
6.    

orl-mus LD50:1500 mg/kg

     85FZAT    Index of Antibiotics from Actinomycetes Umezawa, H., et al., eds.,Tokyo, Japan.: University of Tokyo Press,1967,517.
7.    

ipr-mus LD50:96 mg/kg

     NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),639.
8.    

ivn-dog LD50:18 mg/kg

     ANTCAO    Antibiotics and Chemotherapy. 9 (1959),406.
9.    

orl-rbt LD50:1420 mg/kg

     TXAPA9    Toxicology and Applied Pharmacology. 8 (1966),97.                       

Pimaricin Safety Profile

Poison by intravenous, intramuscular, subcutaneous, and intraperitoneal routes. Moderately toxic by ingestion. When heated to decomposition, it emits toxic fumes of NOx.
Hazard Codes:  HarmfulXn
Risk Statements:  22 
R22:Harmful if swallowed.
Safety Statements:  24/25-36 
S24/25:Avoid contact with skin and eyes. 
S36:Wear suitable protective clothing.
WGK Germany:  2
RTECS:  TK3325000
F:  8-10

Pimaricin Specification

 Pimaricin (CAS NO.7681-93-8) is a naturally occurring antifungal agent produced during fermentation by the bacterium Streptomyces natalensis, commonly found in soil. It has some synonyms like Natamycin ; Pimaricin approx. 2.5% aqueous*suspension gamma-I ; Pimafucin (pimaricin in 2.5% sterile water suspen ; Pimaricin, Streptomyces chattanoogensis (1.07360) and so on.

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