Pimaricin supplier | CasNO.7681-93-8

Name
Pimaricin
EINECS 231-683-5
CAS No. 7681-93-8
Article Data12
CAS DataBase
Density 1.0 g/mL at 20 °C(lit.)
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
Appearance white to off-white solid
Safety 24/25-36
Risk Codes 22
Molecular Structure
Hazard Symbols Xn
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;
PSA 230.99000
LogP 0.82000

Synthetic route

: 127-09-3
sodium acetate

A: 85496-13-5
AB-400

B: 7681-93-8
natamycin

Conditions

Conditions	Yield
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

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

: 4,5-desepoxypimaricin

: 7681-93-8
natamycin

Conditions

Conditions	Yield
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

Conditions	Yield
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%

...Expand

: 4712-55-4
diphenyl hydrogen phosphite

: 7681-93-8
natamycin

: 1122-91-4
4-bromo-benzaldehyde

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

Conditions

Conditions	Yield
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%

...Expand

: 7681-93-8
natamycin

: 1122-91-4
4-bromo-benzaldehyde

: 868-85-9
Dimethyl phosphite

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

Conditions

Conditions	Yield
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%

...Expand

: 1809-19-4
dibutyl hydrogen phosphite

: 7681-93-8
natamycin

: 1122-91-4
4-bromo-benzaldehyde

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

Conditions

Conditions	Yield
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%

...Expand

: 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

Conditions	Yield
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%

...Expand

: C37H34BF3N4O2

: 7681-93-8
natamycin

: C70H80BF2N5O15

Conditions

Conditions	Yield
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

Conditions	Yield
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%

: 7681-93-8
natamycin

: 123-11-5
4-methoxy-benzaldehyde

: 1108187-81-0
N-[(α-hydrophosphoryl-4-methoxybenzyl)]pimaricin

Conditions

Conditions	Yield
Stage #1: natamycin; 4-methoxy-benzaldehyde With triethylamine In dimethyl sulfoxide at 40℃; for 3h; Stage #2: With hypophosphorous acid In dimethyl sulfoxide at 30 - 35℃; Further stages.;	71%

: 7681-93-8
natamycin

: 104-88-1
4-chlorobenzaldehyde

: 1108187-86-5
N-(α-hydrophosphoryl-4-chlorobenzyl)pimaricin

Conditions

Conditions	Yield
Stage #1: natamycin; 4-chlorobenzaldehyde With triethylamine In dimethyl sulfoxide at 40℃; for 3h; Stage #2: With hypophosphorous acid In dimethyl sulfoxide at 30 - 35℃; Further stages.;	70%

: 7681-93-8
natamycin

: 1122-91-4
4-bromo-benzaldehyde

: 1108187-87-6
N-(α-hydrophosphoryl-4-bromobenzyl)pimaricin

Conditions

Conditions	Yield
Stage #1: natamycin; 4-bromo-benzaldehyde With triethylamine In dimethyl sulfoxide at 40℃; for 3h; Stage #2: With hypophosphorous acid In dimethyl sulfoxide at 30 - 35℃; Further stages.;	70%

: 7681-93-8
natamycin

: 100-10-7
4-dimethylamino-benzaldehyde

: 1108187-84-3
N-[α-hydrophosphoryl-4-(dimethylamino)benzyl]pimaricin

Conditions

Conditions	Yield
Stage #1: natamycin; 4-dimethylamino-benzaldehyde With triethylamine In dimethyl sulfoxide at 40℃; for 3h; Stage #2: With hypophosphorous acid In dimethyl sulfoxide at 30 - 35℃; Further stages.;	69%

: 7681-93-8
natamycin

: 123-08-0
4-hydroxy-benzaldehyde

: 1108187-80-9
N-(α-hydrophosphoryl-4-hydroxybenzyl)pimaricin

Conditions

Conditions	Yield
Stage #1: natamycin; 4-hydroxy-benzaldehyde With triethylamine In dimethyl sulfoxide at 40℃; for 3h; Stage #2: With hypophosphorous acid In dimethyl sulfoxide at 30 - 35℃; Further stages.;	67%

: 7681-93-8
natamycin

: 555-16-8
4-nitrobenzaldehdye

: 1108187-82-1
N-[(α-hydrophosphoryl-4-nitrobenzyl)]pimaricin

Conditions

Conditions	Yield
Stage #1: natamycin; 4-nitrobenzaldehdye With triethylamine In dimethyl sulfoxide at 40℃; for 3h; Stage #2: With hypophosphorous acid In dimethyl sulfoxide at 30 - 35℃; Further stages.;	62%

: 4233-33-4
4-Phenyl-1,2,4-triazolidine-3,5-dione

: 7681-93-8
natamycin

: C41H52N4O15

Conditions

Conditions	Yield
With (1S)-10-camphorsulfonic acid In 1,4-dioxane at 20℃; for 3h; Diels-Alder reaction; regioselective reaction;	52%

: 53064-79-2
iodomethyl pivaloate

: 7681-93-8
natamycin

: 1112350-04-5
natamycin methyl pivalate

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at -5℃; for 1h; Inert atmosphere;	12.8%
Stage #1: natamycin With triethylamine In N,N-dimethyl-formamide at -5℃; Inert atmosphere; Stage #2: iodomethyl pivaloate In N,N-dimethyl-formamide for 1h;	12.8%

: 67-56-1
methanol

: 7681-93-8
natamycin

: methyl D-mycosamide hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride 0.5 h; 2 h, reflux then RT, overnight; Yield given;

: 7681-93-8
natamycin

: 267410-86-6
3-(N-(9-fluorenylmethoxycarbonyl)amino)propionaldehyde

: 22-(4-{bis-[3-(9H-fluoren-9-ylmethoxycarbonylamino)-propyl]-amino}-3,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxa-tricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid

Conditions

Conditions	Yield
With hydrogenchloride; sodium cyanoborohydride In N,N-dimethyl-formamide at 20℃; for 16h;
With hydrogenchloride; water; sodium cyanoborohydride In N,N-dimethyl-formamide at 20℃; for 16h;

: 7681-93-8
natamycin

: 85496-13-5
AB-400

Conditions

Conditions	Yield
With Streptomyces diastaticus var. 108; plasmid pSM784; introduced in (S. diastaticus var. 108/784); cell-free extract of Product distribution / selectivity; Enzymatic reaction; Microbiological reaction;
With Streptomyces sp. RGU5.3; cell-free extract of Product distribution / selectivity; Enzymatic reaction; Microbiological reaction;

: 7681-93-8
natamycin

: N,N-di-(3-aminopropyl)-Pimaricin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH3CN; HCl / dimethylformamide / 16 h / 20 °C 2: 22 percent / piperidine / dimethylsulfoxide / 2 h / 20 °C View Scheme

: 7681-93-8
natamycin

: C49H58N2O14

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / N,N-dimethyl-formamide; methanol / 12 h / 20 °C 2: camphor-10-sulfonic acid / methanol; tetrahydrofuran / 1 h / 0 °C 3: diphenyl phosphoryl azide; triethylamine / tetrahydrofuran / 3 h / 50 °C View Scheme

: 7681-93-8
natamycin

: NatMU

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine / N,N-dimethyl-formamide; methanol / 12 h / 20 °C 2: camphor-10-sulfonic acid / methanol; tetrahydrofuran / 1 h / 0 °C 3: diphenyl phosphoryl azide; triethylamine / tetrahydrofuran / 3 h / 50 °C 4: tetrahydrofuran / 16 h / 20 °C View Scheme

: 7681-93-8
natamycin

: NatAU

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine / N,N-dimethyl-formamide; methanol / 12 h / 20 °C 2: camphor-10-sulfonic acid / methanol; tetrahydrofuran / 1 h / 0 °C 3: diphenyl phosphoryl azide; triethylamine / tetrahydrofuran / 3 h / 50 °C 4: tetrahydrofuran / 2 h / 50 °C View Scheme

: 7681-93-8
natamycin

: C49H59NO15

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / N,N-dimethyl-formamide; methanol / 12 h / 20 °C 2: camphor-10-sulfonic acid / methanol; tetrahydrofuran / 1 h / 0 °C View Scheme

: 82911-69-1
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

: 7681-93-8
natamycin

: C48H57NO15

Conditions

Conditions	Yield
With pyridine In methanol; N,N-dimethyl-formamide at 20℃; for 12h;

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 NO_x.
Hazard Codes: Harmful Xn
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.

Product Name

Pimaricin

Synthetic route

Pimaricin Chemical Properties

Pimaricin Uses

Pimaricin Toxicity Data With Reference

Pimaricin Safety Profile

Pimaricin Specification

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