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Cycloleucine

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Name

Cycloleucine

EINECS 200-144-6
CAS No. 52-52-8 Density 1.207 g/cm3
PSA 63.32000 LogP 1.04280
Solubility 5 g/100 mL in waier Melting Point 320 °C (dec.)(lit.)
Formula C6H11NO2 Boiling Point 256.1 °C at 760 mmHg
Molecular Weight 129.159 Flash Point 108.7 °C
Transport Information UN 2811 6.1/PG 3 Appearance white to beige crystalline flakes or powder
Safety 22-24/25 Risk Codes 22
Molecular Structure Molecular Structure of 52-52-8 (Cycloleucine) Hazard Symbols IrritantXi, HarmfulXn
Synonyms

1-Amino-1-carboxycyclopentane;1-Aminocyclopentane-1-carboxylic acid;1-Aminocyclopentanecarboxylic acid;ACPC;Cycloleucin;NSC 1026;NSC 112194;NSC 112195;NSC 112197;WR 14997;

Article Data 18

Cycloleucine Synthetic route

49830-37-7

1-amino-1-cyanocyclopentane

52-52-8

1-amino-1-cyclopentanecarboxylic acid

Conditions
ConditionsYield
With hydrogenchloride; water In 1,4-dioxane for 8h; Inert atmosphere; Reflux;99%
With hydrogenchloride
699-51-4

1,3-diazaspiro[4.4]nonane-2,4-dione

52-52-8

1-amino-1-cyclopentanecarboxylic acid

Conditions
ConditionsYield
With sodium hydroxide Heating;75%
With barium dihydroxide In water for 3h; Heating;71%
With barium hydroxide octahydrate; water In water at 160℃; for 2h; Autoclave;70%
2627-43-2

1-hydroxyamino-cyclopentanecarboxylic acid

52-52-8

1-amino-1-cyclopentanecarboxylic acid

Conditions
ConditionsYield
With ammonium hydroxide; palladium Hydrogenation;
151-50-8

potassium cyanide

120-92-3

cyclopentanone

52-52-8

1-amino-1-cyclopentanecarboxylic acid

Conditions
ConditionsYield
With ethanol; ammonium chloride Verseifen des Nitrils durch Erhitzen mit Salzsaeure;
89985-89-7

1-<(Diphenylmethylene)-amino>-1-cyclopentanecarbonitrile

52-52-8

1-amino-1-cyclopentanecarboxylic acid

Conditions
ConditionsYield
With hydrogenchloride 1.) ether, 12 h, room temp., 2.) reflux; Yield given. Multistep reaction;
1,3-diaza-spiro<4,4>nonanedione-(2,4)

1,3-diaza-spiro<4,4>nonanedione-(2,4)

52-52-8

1-amino-1-cyclopentanecarboxylic acid

Conditions
ConditionsYield
With sulfuric acid at 140℃;
120-92-3

cyclopentanone

52-52-8

1-amino-1-cyclopentanecarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 64 percent / (NH4)2CO3 / ethanol; H2O / 2 h / 58 - 60 °C
2: 71 percent / Ba(OH)2*8H2O / H2O / 3 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: H2O; NH2OH+HCl
2: aqueous HCl
3: palladium; aqueous NH3 / Hydrogenation
View Scheme
Multi-step reaction with 2 steps
1: ammonium chloride; ammonium hydroxide / isopropyl alcohol / 20 °C / Inert atmosphere
2: hydrogenchloride; water / 1,4-dioxane / 8 h / Inert atmosphere; Reflux
View Scheme
120-92-3

cyclopentanone

furan(?)

furan(?)

52-52-8

1-amino-1-cyclopentanecarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ethanol; H2O / Heating
2: 60percent H2SO4 / 10 h / 140 °C
View Scheme
120-92-3

cyclopentanone

diluted alcoholic KOH

diluted alcoholic KOH

52-52-8

1-amino-1-cyclopentanecarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 73 percent / ethanol; H2O / 6 h / Heating
2: 75 percent / 3 N aq. NaOH / Heating
View Scheme
1192-28-5

Cyclopentanone oxime

52-52-8

1-amino-1-cyclopentanecarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aqueous NaHSO3
2: aqueous HCl
3: palladium; aqueous NH3 / Hydrogenation
View Scheme

Cycloleucine Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Cycloleucine Specification

The IUPAC name of Cycloleucine is 1-aminocyclopentane-1-carboxylic acid. With the CAS registry number 52-52-8, it is also named as Cyclopentanecarboxylic acid, 1-amino-, L-. The product's categories are Pharmacetical; Amino Acids; Amino Acids; Amino Acids & Derivatives; Cycloalkanes, and the other registry number is 15313-85-6. Besides, it is white to beige crystalline flakes or powder, which should be stored in sealed, cool and dry place at room temperature. In addition, its molecular formula is C6H11NO2 and molecular weight is 129.16.

The other characteristics of this product can be summarized as: (1)EINECS: 200-144-6; (2)ACD/LogP: -0.05; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): -2.55; (5)ACD/LogD (pH 7.4): -2.55; (6)ACD/BCF (pH 5.5): 1; (7)ACD/BCF (pH 7.4): 1; (8)ACD/KOC (pH 5.5): 1; (9)ACD/KOC (pH 7.4): 1; (10)#H bond acceptors: 3; (11)#H bond donors: 3; (12)#Freely Rotating Bonds: 2; (13)Index of Refraction: 1.522; (14)Molar Refractivity: 32.62 cm3; (15)Molar Volume: 106.9 cm3; (16)Surface Tension: 53.2 dyne/cm; (17)Density: 1.207 g/cm3; (18)Flash Point: 108.7 °C; (19)Melting point: 320 °C; (20)Water solubility: 5 g/100 mL; (21)Enthalpy of Vaporization: 54.35 kJ/mol; (22)Boiling Point: 256.1 °C at 760 mmHg; (23)Vapour Pressure: 0.00481 mmHg at 25 °C.

Preparation of Cycloleucine: this chemical can be prepared by 1,3-Diaza-spiro[4.4]nonane-2,4-dione.



This reaction needs 3 N aq. NaOH by heating. The yield is 75 %.

Uses of Cycloleucine:  this chemical is a non-metabolisable amino acid. It is a specific and reversible inhibitor of nucleic acid methylation. It is widely used in biochemical experiments. Additionally, it can react with Ethanol to get 1-Amino-cyclopentanecarboxylic acid ethyl ester.



This reaction needs HCl. The yield is 86.5 %.

When you are using this chemical, please be cautious about it as the following: it is harmful if swallowed. Please do not breathe dust. And you should avoid contact with skin and eyes.

People can use the following data to convert to the molecule structure.
(1)SMILES: O=C(O)C1(N)CCCC1
(2)InChI: InChI=1/C6H11NO2/c7-6(5(8)9)3-1-2-4-6/h1-4,7H2,(H,8,9)
(3)InChIKey: NILQLFBWTXNUOE-UHFFFAOYAN
(4)Std. InChI: InChI=1S/C6H11NO2/c7-6(5(8)9)3-1-2-4-6/h1-4,7H2,(H,8,9)
(5)Std. InChIKey: NILQLFBWTXNUOE-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 4gm/kg (4000mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 469, 1971.
dog LD50 intravenous 300mg/kg (300mg/kg)   Journal of Medicinal and Pharmaceutical Chemistry. Vol. 3, Pg. 1, 1961.
dog LD50 oral 300mg/kg (300mg/kg)   Journal of Medicinal and Pharmaceutical Chemistry. Vol. 3, Pg. 1, 1961.
guinea pig LD50 oral 140mg/kg (140mg/kg)   Journal of Medicinal and Pharmaceutical Chemistry. Vol. 3, Pg. 1, 1961.
human TDLo oral 60mg/kg (60mg/kg) BEHAVIORAL: ANOREXIA (HUMAN

GASTROINTESTINAL: NAUSEA OR VOMITING
Journal of Medicinal and Pharmaceutical Chemistry. Vol. 3, Pg. 1, 1961.
mouse LD50 intraperitoneal 119mg/kg (119mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 oral 309mg/kg (309mg/kg)   Journal of Medicinal and Pharmaceutical Chemistry. Vol. 3, Pg. 1, 1961.
mouse LD50 subcutaneous 375mg/kg (375mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
quail LD50 oral > 316mg/kg (316mg/kg)   Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982.
rat LD50 intravenous 340mg/kg (340mg/kg)   Journal of Medicinal and Pharmaceutical Chemistry. Vol. 3, Pg. 1, 1961.
rat LD50 oral 290mg/kg (290mg/kg)   Journal of Medicinal and Pharmaceutical Chemistry. Vol. 3, Pg. 1, 1961.
 

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