D-alpha-Cyclohexylglycine
Description References- Product Name
- D-alpha-Cyclohexylglycine
- CAS No.
- 14328-52-0
- Chemical Name
- D-alpha-Cyclohexylglycine
- Synonyms
- D-CHG;D-αD-CHG-OH;H-D-CHG-OH;D-Chg-OH·TFA;H-D-CHG-OH TFA;-Hydrazino-αD-Cyclohexyglycine;D-CYCLOHEXYLGLYCINE;H-PHG(HEXAHYDRO)-OH
- CBNumber
- CB8234915
- Molecular Formula
- C8H15NO2
- Formula Weight
- 157.21
- MOL File
- 14328-52-0.mol
D-alpha-Cyclohexylglycine Property
- Melting point:
- 256 °C
- alpha
- -34.5 º (c=0.4 5N HCl)
- Boiling point:
- 292.8±23.0 °C(Predicted)
- Density
- 1.120±0.06 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- DMSO
- pka
- 2.44±0.10(Predicted)
- form
- Solid
- color
- Off-White
- Water Solubility
- Soluble
- BRN
- 3196806
- InChI
- InChI=1/C8H15NO2/c9-7(8(10)11)6-4-2-1-3-5-6/h6-7H,1-5,9H2,(H,10,11)/t7-/s3
- InChIKey
- WAMWSIDTKSNDCU-SSDOTTSWSA-N
- SMILES
- C1(CCCCC1)[C@@H](N)C(=O)O |&1:6,r|
- CAS DataBase Reference
- 14328-52-0(CAS DataBase Reference)
Safety
- Hazard Codes
- Xi
- Risk Statements
- 36/37/38
- Safety Statements
- 37/39-26-24/25
- WGK Germany
- 3
- HS Code
- 29224999
N-Bromosuccinimide Price
- Product number
- 61844
- Product name
- D-α-Cyclohexylglycine
- Purity
- ≥98.0% (HPLC)
- Packaging
- 5G
- Price
- $139
- Updated
- 2025/07/31
- Product number
- C2673
- Product name
- D-2-Cyclohexylglycine
- Purity
- >98.0%(HPLC)(T)
- Packaging
- 1g
- Price
- $110
- Updated
- 2025/07/31
- Product number
- C987935
- Product name
- D-Cyclohexylglycine
- Packaging
- 1g
- Price
- $55
- Updated
- 2021/12/16
- Product number
- 237057
- Product name
- D-2-Cyclohexylglycine trifluoroacetate
- Packaging
- 1g
- Price
- $200
- Updated
- 2021/12/16
- Product number
- 268834
- Product name
- D-Cyclohexylglycine
- Packaging
- 1g
- Price
- $372
- Updated
- 2021/12/16
D-alpha-Cyclohexylglycine Chemical Properties,Usage,Production
Description
D-alpha-Cyclohexylglycine is a kind of non-proteinogenic amino acid. It is widely presented in various natural products and pharmaceutical intermediates. It can be incorporated into the peptide inhibitors renders resistance from peptidases and proteinases and thereby imparts pharmacological stability to molecules. Some derivatives of Cyclohexylglycine has been recently been developed into inhibitors of the dipeptidyl peptidase-IV enzyme (“DP-IV inhibitors”) and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly type 2 diabetes.
References
https://www.qmbio.com/?shopp_category=chg
Edmondson, Scott D., A. Mastracchio, and E. R. Parmee. "CYCLOHEXYLGLYCINE DERIVATIVES AS DIPEPTIDYL PEPTIDASE INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES." (2008).
Mastracchio, Anthony, et al. "Heterocycle-Fused Cyclohexylglycine Derivatives as Novel Dipeptidyl Peptidase-IV Inhibitors. " Cheminform 35.35(2004):203-206.
Chemical Properties
white powder
Uses
D-Cyclohexylglycine (cas# 14328-52-0) is a compound useful in organic synthesis.
reaction suitability
reaction type: solution phase peptide synthesis
Synthesis
875-74-1
14328-52-0
The general procedure for synthesizing D-cyclohexylglycine from levophenylglycine is as follows: Example 1: Preparation of D-cyclohexylglycine 100 g (661.5 mmol) of D-phenylglycine was dissolved or suspended in a mixture of 890 ml of deionized water, 290 ml of isopropanol and 66.7 ml (802 mmol) of 37% hydrochloric acid. 10 g of Pt/Rh catalyst (4% Pt + 1% Rh loaded on activated carbon with about 50% water, corresponding to about 5 wt% of the amount of D-phenylglycine) was added. The reaction mixture was transferred to a 2 liter hydrogenation autoclave. It was displaced three times with nitrogen and then flushed twice with hydrogen, after which a hydrogen pressure of 8-10 bar was established and the reaction system was heated to 50-60°C. After about 6 to 8 hours of reaction, the hydrogen uptake was complete (theoretical H2 uptake of 44.4 L). The hydrogen was released by depressurization and again replaced three times with nitrogen. The reaction solution was filtered while hot and the catalyst was washed with 200 ml of deionized water. The filtrate was first adjusted to pH 2-2.5 with 50% sodium hydroxide solution at 40-60°C, at which point crystals began to precipitate. The pH was maintained and stirred for 15-30 min, then adjusted to pH 5-6 with 50% sodium hydroxide solution.The reaction mixture was cooled to 0-10 °C in an ice bath, the product was collected by filtration, washed with 300 ml of deionized water and dried in a vacuum oven at 50-70 °C. The catalyst can be reused for several times without any problem. The catalyst can be reused several times without deactivation. Yield: 100-102 g (95.8-97.7% yield). 1H-NMR (500 MHz, D2O/NaOD): δ (ppm) = 1-1.26 and 1.53-1.75 (both m, combined 11H, cyclohexyl proton), 3.02 (d, 1H, α-proton). The enantiomeric purity of the resulting D-cyclohexylglycine was consistent with that of the starting material D-phenylglycine by chiral GC analysis.
References
[1] Patent: WO2005/14526, 2005, A1. Location in patent: Page/Page column 12
[2] Chemische Berichte, 1986, vol. 119, # 7, p. 2191 - 2207
[3] Journal of Organic Chemistry, 1983, vol. 48, # 13, p. 2195 - 2202
[4] Justus Liebigs Annalen der Chemie, 1936, vol. 523, p. 199,203
[5] Il Farmaco; edizione scientifica, 1971, vol. 26, # 5, p. 474 - 486
D-alpha-Cyclohexylglycine Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from D-alpha-Cyclohexylglycine manufacturers
- Product
- D-alpha-Cyclohexylglycine 14328-52-0
- Price
- US $0.00/Kg/Drum
- Min. Order
- 1KG
- Purity
- 99%min
- Supply Ability
- 1000kg
- Release date
- 2021-08-31
- Product
- D-Cyclohexylglycine 14328-52-0
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 97.8%
- Supply Ability
- 100 tons
- Release date
- 2022-01-26
- Product
- D-Chg-OH 14328-52-0
- Price
- US $1.00/g
- Min. Order
- 1g
- Purity
- 98%
- Supply Ability
- 100KG
- Release date
- 2019-07-23