ChemicalBook > CAS DataBase List > D-alpha-Cyclohexylglycine

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

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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)

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 37/39-26-24/25
WGK Germany: 3
HS Code: 29224999

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word: Warning

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 61844
Product name: D-α-Cyclohexylglycine
Purity: ≥98.0% (HPLC)
Packaging: 5G
Price: $139
Updated: 2025/07/31

TCI Chemical

Product number: C2673
Product name: D-2-Cyclohexylglycine
Purity: >98.0%(HPLC)(T)
Packaging: 1g
Price: $110
Updated: 2025/07/31

Usbiological

Product number: 237057
Product name: D-2-Cyclohexylglycine trifluoroacetate
Packaging: 1g
Price: $200
Updated: 2021/12/16

Usbiological

Product number: 268834
Product name: D-Cyclohexylglycine
Packaging: 1g
Price: $372
Updated: 2021/12/16

Usbiological

Product number: 007286
Product name: D-Cyclohexylglycine
Packaging: 250mg
Price: $403
Updated: 2021/12/16

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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

WUHAN FORTUNA CHEMICAL CO., LTD

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

Honest Joy Holdings Limited

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

Sichuan Jiaying Lai Technology Co.,LTD

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

14328-52-0, D-alpha-CyclohexylglycineRelated Search:

Cyclohexanecarboxylic acid 4-Aminophenylacetic acid Isocyanatocyclohexane Folic acid Diethylstilbestrol Molasses Nitrilotriacetic acid Iminodiacetic acid (Aminomethyl)cyclohexane Cyclohexylacetic acid Glycine Hyaluronic acid Ethyl 2-(Chlorosulfonyl)acetate Sodium N-cyclohexylsulfamate Citric acid α-Lipoic Acid Ascoric Acid FMOC-D-ALPHA-CYCLOHEXYLGLYCINE,FMOC-CYCLOHEXYL-D-GLYCINE

D-CHG-OH

D-&alpha

(R)-2-Cyclohexylglycine

D-α-AMinocyclohexaneacetic Acid

D-Chg-OH·TFA

D-Cyclohexylglycine,99%e.e.

(R)-CYCLOHEXYLGLYCINE

(R)-AMINO-CYCLOHEXYL-ACETIC ACID

(R)-(+)-ALPHA-AMINOCYCLOHEXYLACETIC ACID

(R)-ALPHA-AMINOCYCLOHEXYLACETIC ACID

D-CYCLOHEXYLGLYCINE

D-CHG

D-2-CYCLOHEXYL-GLYCINE

D-2-CYCLOHEXYLGLYCINE TRIFLUOROACETATE

D-ALPHA-CYCLOHEXYLGLYCINE

CYCLOHEXYL-D-GLYCINE

H-PHG(HEXAHYDRO)-OH

H-D-CHG-OH

H-D-CHG-OH TFA

H-CYCLOHEXYL-D-GLY-OH

H-CYCLOHEXYL-D-GLY-OH TFA

2-CYCLOHEXYL-D-GLYCINE

H-D-Cyclohexyl-Gly-OH

D-Cyclohexyglycine

(2S)-amino(cyclohexyl)acetic acid

D-CYCLOHEXYLGLYCINE 98%

(R)-2-amino-2-cyclohexylaceticacid

D-alpha-Cyclohexylglycine,98%

D-α-Cyclohexylglycine, 98.0%

-Bromocamphor-8-sulfonic Acid Ammonium Salt

-(3,4-dihydroxyphenyl)propionic Acid (Mixture of Diasteromers)

-Hydrazino-&alpha

D-2-Cyclohexylglycine &gt

Cyclohexaneacetic acid, α-amino-, (αR)-

D-α-Cyclohexylglycine

D-alpha-Cyclohexylglycine USP/EP/BP

D-α-Aminocyclohexylacetic acid

D-alpha-Cyclohexylglycine 14328-52-0

(αR)-α-Aminocyclohexaneacetic acid

<sc>D</sc>-α-Cyclohexylglycine

(alphaR)-alpha-Aminocyclohexaneacetic acid

14328-52-0

C8H15NO2C2HF3O2

Glycine Derivatives

Specialty Synthesis

Peptide Synthesis

Unnatural Amino Acid Derivatives

Amino Acids & Derivatives

Chiral Reagents

Miscellaneous Reagents

Peptide