Product Name

  • Name

    Chlorotetracycline

  • EINECS 200-341-7
  • CAS No. 57-62-5
  • Density 1.7 g/cm3
  • Solubility 0.63g/L(25 oC)
  • Melting Point 168.5oC
  • Formula C22H23ClN2O8
  • Boiling Point 821.078 °C at 760 mmHg
  • Molecular Weight 478.886
  • Flash Point 450.372 °C
  • Transport Information
  • Appearance Golden yellow crystal powder
  • Safety
  • Risk Codes 22
  • Molecular Structure Molecular Structure of 57-62-5 (Chlorotetracycline)
  • Hazard Symbols HarmfulXn
  • Synonyms 2-Naphthacenecarboxamide,7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-(7CI,8CI);2-Naphthacenecarboxamide,7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-,[4S-(4a,4aa,5aa,6b,12aa)]-;Aureomicina;Aureomycin;Aureomykoin;Aurofac;Aureocina;A-Mycin;Acronize;7-Chlorotetracycline;7-Chlortetracycline;Tri-chlortetracycline;Acronize PD;Chrysomykine;Chlortetracycline;Centraureo;Chlorocyclinum;
  • PSA 181.62000
  • LogP 1.13930

Synthetic route

methanol
67-56-1

methanol

4-epi chlortetracycline
14297-93-9

4-epi chlortetracycline

NaH2PO4

NaH2PO4

Chlortetracycline
57-62-5

Chlortetracycline

Conditions
ConditionsYield
Gleichgeweicht;
...Expand
Chlortetracycline
57-62-5

Chlortetracycline

A

C20H16ClNO9

C20H16ClNO9

B

4-(((1S,4R,10S)-9-chloro-6-hydroxy-1-methyl-3,5-dioxo-1,3,4,5-tetrahydro-1,4-methanobenzo[c]oxepin-10-yl)methyl)-2,3,5,6-tetrahydroxybenzamide

4-(((1S,4R,10S)-9-chloro-6-hydroxy-1-methyl-3,5-dioxo-1,3,4,5-tetrahydro-1,4-methanobenzo[c]oxepin-10-yl)methyl)-2,3,5,6-tetrahydroxybenzamide

Conditions
ConditionsYield
With mercury(II) diacetate; magnesium sulfate; acetic acid; sodium hydroxide In tetrahydrofuran at 50℃; for 48h;A 17.5%
B 34%
Chlortetracycline
57-62-5

Chlortetracycline

isochlortetracycline
514-53-4

isochlortetracycline

Conditions
ConditionsYield
With sodium hydroxide
With potassium hydroxide
Chlortetracycline
57-62-5

Chlortetracycline

(S)-4-((1S)-4-carbamoyl-2t-dimethylamino-3,6ξ-dihydroxy-5-oxo-cyclohex3-en-r-yl)-3-((S)-7-chloro-4-hydroxy-1-methyl-3-oxo-phthalan-1-yl)-butyric acid
3811-34-5, 66749-14-2, 66749-15-3

(S)-4-((1S)-4-carbamoyl-2t-dimethylamino-3,6ξ-dihydroxy-5-oxo-cyclohex3-en-r-yl)-3-((S)-7-chloro-4-hydroxy-1-methyl-3-oxo-phthalan-1-yl)-butyric acid

Conditions
ConditionsYield
With sodium hydroxide; sodium dithionite β-aureomycinic acid;
With sodium hydroxide; sodium dithionite α-aureomycinic acid;
With sodium hydroxide; zinc β-aureomycinic acid;
Chlortetracycline
57-62-5

Chlortetracycline

4-methoxyphthalic acid
1885-13-8

4-methoxyphthalic acid

Conditions
ConditionsYield
Behandeln des Reaktionsprodukts mit KMnO4;
Chlortetracycline
57-62-5

Chlortetracycline

TETRACYCLINE
60-54-8

TETRACYCLINE

Conditions
ConditionsYield
With palladium on activated charcoal; 2-methoxy-ethanol; triethylamine Hydrogenation;
With 1,4-dioxane; methanol; palladium on activated charcoal Hydrogenation;
Chlortetracycline
57-62-5

Chlortetracycline

anhydrotetracycline
1665-56-1, 7518-17-4

anhydrotetracycline

Conditions
ConditionsYield
With hydrogen iodide
Chlortetracycline
57-62-5

Chlortetracycline

(4S,4aS,12aS)-7-chloro-4-(dimethylamino)-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-1,4,4a,5,12,12a-hexahydrotetracene-2-carboxamide
4497-08-9

(4S,4aS,12aS)-7-chloro-4-(dimethylamino)-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-1,4,4a,5,12,12a-hexahydrotetracene-2-carboxamide

Conditions
ConditionsYield
With hydrogenchloride
Chlortetracycline
57-62-5

Chlortetracycline

4-epi chlortetracycline
14297-93-9

4-epi chlortetracycline

Conditions
ConditionsYield
With sodium dihydrogenphosphate; N,N-dimethyl-formamide
Chlortetracycline
57-62-5

Chlortetracycline

(S)-4-(4-carbamoyl-2,3,5-trihydroxy-phenyl)-3-((S)-7-chloro-4-hydroxy-1-methyl-3-oxo-phthalan-1-yl)-butyric acid
3811-33-4, 66749-13-1

(S)-4-(4-carbamoyl-2,3,5-trihydroxy-phenyl)-3-((S)-7-chloro-4-hydroxy-1-methyl-3-oxo-phthalan-1-yl)-butyric acid

Conditions
ConditionsYield
With sodium hydroxide
Chlortetracycline
57-62-5

Chlortetracycline

(R)-7-chloro-4-methoxy-1-methyl-3-oxo-phthalan-1-carboxylic acid
94971-39-8

(R)-7-chloro-4-methoxy-1-methyl-3-oxo-phthalan-1-carboxylic acid

Conditions
ConditionsYield
durch Methylierung und Oxydation dargestellt;
Chlortetracycline
57-62-5

Chlortetracycline

dimethyl sulfate
77-78-1

dimethyl sulfate

3-((S)-7-chloro-4-methoxy-1-methyl-3-oxo-phthalan-1-yl)-glutaric acid

3-((S)-7-chloro-4-methoxy-1-methyl-3-oxo-phthalan-1-yl)-glutaric acid

Conditions
ConditionsYield
With sodium carbonate anschliessend Behandeln mit wss. Natronlauge und mit Kaliumpermanganat;
Chlortetracycline
57-62-5

Chlortetracycline

aqueous NaOH

aqueous NaOH

isochlortetracycline
514-53-4

isochlortetracycline

methanol
67-56-1

methanol

Chlortetracycline
57-62-5

Chlortetracycline

NaH2PO4

NaH2PO4

4-epi chlortetracycline
14297-93-9

4-epi chlortetracycline

Conditions
ConditionsYield
Gleichgewicht;
...Expand
hydrogenchloride
7647-01-0

hydrogenchloride

Chlortetracycline
57-62-5

Chlortetracycline

anhydrochlorotetracycline

anhydrochlorotetracycline

hydrogenchloride
7647-01-0

hydrogenchloride

Chlortetracycline
57-62-5

Chlortetracycline

(4S,4aS,12aS)-7-chloro-4-(dimethylamino)-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-1,4,4a,5,12,12a-hexahydrotetracene-2-carboxamide
4497-08-9

(4S,4aS,12aS)-7-chloro-4-(dimethylamino)-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-1,4,4a,5,12,12a-hexahydrotetracene-2-carboxamide

GLUTATHIONE
70-18-8

GLUTATHIONE

Chlortetracycline
57-62-5

Chlortetracycline

2-amino-4-[2-(8-carbamoyl-10-dimethylamino-4,6,6a,9,12-pentahydroxy-12-methyl-5,7-dioxo-5,6a,7,10,10a,11,11a,12-octahydro-naphthacen-1-ylsulfanyl)-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid

2-amino-4-[2-(8-carbamoyl-10-dimethylamino-4,6,6a,9,12-pentahydroxy-12-methyl-5,7-dioxo-5,6a,7,10,10a,11,11a,12-octahydro-naphthacen-1-ylsulfanyl)-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid

Conditions
ConditionsYield
With PBS; glutathione S-transferase at 30℃; for 1h; pH=6.5;
Chlortetracycline
57-62-5

Chlortetracycline

(R)-7-chloro-4-methoxy-1-methyl-3-oxo-phthalan-1-carboxylic acid methyl ester
100062-33-7

(R)-7-chloro-4-methoxy-1-methyl-3-oxo-phthalan-1-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: durch Methylierung und Oxydation dargestellt
View Scheme
Chlortetracycline
57-62-5

Chlortetracycline

de(dimethylamino)chlorotetracycline
4632-89-7

de(dimethylamino)chlorotetracycline

Conditions
ConditionsYield
Stage #1: Chlortetracycline With acetic acid; zinc In water for 2h;
Stage #2: With hydrogenchloride In water; acetic acid for 0.5h;
Chlortetracycline
57-62-5

Chlortetracycline

6-iso-7-chlortetracycline

6-iso-7-chlortetracycline

Conditions
ConditionsYield
Alkaline conditions;
Chlortetracycline
57-62-5

Chlortetracycline

C21H23ClN2O8

C21H23ClN2O8

Conditions
ConditionsYield
With D-glucose 6-phosphate; nicotinamide adenine dinucleotide phosphate; magnesium chloride In water Catalytic behavior; Reagent/catalyst; Enzymatic reaction;

Chlorotetracycline Specification

The Chlortetracycline, with the CAS registry number 57-62-5, is also known as 7-Chlorotetracycline. It belongs to the product categories of Pharmaceuticals. Its EINECS registry number is 200-341-7. This chemical's molecular formula is C22H23ClN2O8 and molecular weight is 478.88. Its IUPAC name is called (4S,4αS,5αS,6S,12αS,Z)-2-[amino(hydroxy)methylene]-7-chloro-4-(dimethylamino)-6,10,11,12α-tetrahydroxy-6-methyl-4α,5,5α,6-tetrahydrotetracene-1,3,12(2H,4H,12αH)-trione. This chemical's classification codes are Agricultural Chemical; Anti-Bacterial Agents; Anti-Infective Agents; Antibacterial; Antiparasitic Agents; Antiprotozoal; Antiprotozoal agents; Drug / Therapeutic Agent; Enzyme Inhibitors; Fungicide, bactericide, wood preservative; Protein Synthesis Inhibitors; Reproductive Effect. When you are using this chemical, please be cautious about it. This chemical may cause damage to health. It is harmful if swallowed.

Physical properties of Chlortetracycline: (1)ACD/LogP: 1.32; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): -3; (4)ACD/LogD (pH 7.4): -4; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 10; (10)#H bond donors: 7; (11)#Freely Rotating Bonds: 7; (12)Index of Refraction: 1.745; (13)Molar Refractivity: 113.915 cm3; (14)Molar Volume: 281.089 cm3; (15)Surface Tension: 101.962 dyne/cm; (16)Density: 1.704 g/cm3; (17)Flash Point: 450.372 °C; (18)Enthalpy of Vaporization: 125.108 kJ/mol; (19)Boiling Point: 821.078 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be prepared by Streptomyces (Streptomyces aureofacieus). This reaction will need solvent ethanol.

Chlortetracycline (trade name Aureomycin, Lederle) is a tetracycline antibiotic, and was the first tetracycline to be discovered. In veterinary medicine, it is commonly used to treat conjunctivitis in cats. What's more, this chemical can be used to inhibit gram-positive and electronegative bacterium, can treat typhoid, white scour and other diseases. It also can be used as promoting growth agent.

You can still convert the following datas into molecular structure:
(1)SMILES: CN(C)[C@@H]2C(\O)=C(\C(N)=O)C(=O)[C@@]3(O)C(/O)=C4/C(=O)c1c(O)ccc(Cl)c1[C@@](C)(O)[C@H]4C[C@@H]23
(2)InChI: InChI=1/C22H23ClN2O8/c1-21(32)7-6-8-15(25(2)3)17(28)13(20(24)31)19(30)22(8,33)18(29)11(7)16(27)12-10(26)5-4-9(23)14(12)21/h4-5,7-8,15,26,28-29,32-33H,6H2,1-3H3,(H2,24,31)/t7-,8-,15-,21-,22-/m0/s1
(3)InChIKey: CYDMQBQPVICBEU-XRNKAMNCBT

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 150mg/kg (150mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 52, 1959.
dog LD50 oral 750mg/kg (750mg/kg)   Antimicrobial Agents Annual. Vol. -, Pg. 595, 1960.
guinea pig LDLo intraperitoneal 1800mg/kg (1800mg/kg)   Antibiotiki. Vol. 20, Pg. 793, 1975.
mouse LD50 intracrebral 48mg/kg (48mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: EXCITEMENT

MUSCULOSKELETAL: CHANGES IN TEETH AND SUPPORTING STRUCTURES		 Chemotherapy Vol. 26, Pg. 196, 1980.
mouse LD50 intravenous 134mg/kg (134mg/kg)   Antibiotics and Chemotherapy Vol. 6, Pg. 623, 1956.
mouse LD50 oral 1500mg/kg (1500mg/kg)   Antimicrobial Agents Annual. Vol. -, Pg. 595, 1960.
mouse LDLo intraperitoneal 192mg/kg (192mg/kg)   Compilation of LD50 Values of New Drugs.
mouse LDLo subcutaneous 3gm/kg (3000mg/kg)   Antibiotics and Chemotherapy Vol. 6, Pg. 623, 1956.
rat LD50 intravenous 118mg/kg (118mg/kg)   Antibiotics and Chemotherapy Vol. 6, Pg. 623, 1956.
rat LDLo intraperitoneal 335mg/kg (335mg/kg)   Compilation of LD50 Values of New Drugs.
rat LDLo oral 3gm/kg (3000mg/kg)   Journal of Agricultural and Food Chemistry. Vol. 17, Pg. 497, 1969.

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