H-D-CHA-OH Chemical Properties

Boiling point:

307.1±25.0 °C(Predicted)

Density 

1.075

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Aqueous Acid (Slightly), Methanol (Slightly), Water (Slightly)

form 

Solid

pka

2.33±0.10(Predicted)

color 

White to Off-White

optical activity

[α]20/D 12±1°, c = 1% in 1 M HCl (dry matter)

BRN 

3197315

InChI

InChI=1/C9H17NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h7-8H,1-6,10H2,(H,11,12)/t8-/s3

InChIKey

ORQXBVXKBGUSBA-MRVPVSSYSA-N

SMILES

C1(CCCCC1)C[C@@H](N)C(=O)O |&1:7,r|

CAS DataBase Reference

58717-02-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29224999

H-D-CHA-OH Usage And Synthesis

Chemical Properties

White to off-white crystalline powder

Uses

(R)-2-amino-3-cyclohexylpropanoic acid is an alanine derivative[1].

Application

H-D-CHA-OH is thrombin inhibitor.

Synthesis

General procedure for the synthesis of (S)-2-Amino-3-cyclohexylpropionic acid and (R)-2-Amino-3-cyclohexylpropionic acid from 3-cyclohexylpropionic acid: pyridoxamine 4a (2.1 mg, 0.0050 mmol), 4-(naphthalen-1-yl)-2-oxo-butyric acid (1a) (22.8 mg, 0.10 mmol), 2,2-diphenylglycine 11 ( 22.7 mg, 0.10 mmol), CH3COOH (48.0 mg, 0.80 mmol), EtOH (0.40 mL), and H2O (0.10 mL) were stirred for 24 hours at 25 °C. Upon completion of the reaction, the mixture was transferred to a 25 mL aubergine flask and methanol (10 mL) was added to completely dissolve the solid, followed by silica gel (0.50 g). The solvent was removed under reduced pressure at 25 °C. The residue was purified by fast column chromatography (silica gel, eluent ratio EtOH/ethyl acetate/25-28% aqueous ammonia solution = 100:58:16) to afford amino acid 2a (22.0 mg, 96% yield, 83% ee) as a white solid. To determine the enantiomeric excess (ee) of 2a, the amino acid was first converted to the corresponding methyl ester by treatment with diazomethane in methanol at room temperature, and subsequently analyzed by HPLC (Chiralcel OD-H column, mobile phase n-hexane: isopropanol = 85:15, flow rate 1.0 mL/min). The enantiomeric excesses (ee) of the products 2b-1 and 2o, as well as the dr values of the products 2m-n, were determined by converting the amino acids to the corresponding N-benzoyl methyl esters by treatment with thionyl chloride in methanol, then reacting with benzoic anhydride, and finally analyzed by HPLC.

References

[1] Luckose F, et al. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1036. DOI:10.1080/10408398.2012.708368

H-D-CHA-OH(58717-02-5)Related Product Information

• H-D-CHA-OH HCL
• H-CHA-OH HCL
• H-L-Cha-OH*HCl,H-CHA-OH HCL,H-L-CHA-OH,H-CHA-OH
• Beta-Cyclohexyl-L-Alanine Benzyl Ester Hydrochloride
• Beta-Cyclohexyl-L-Alanine Benzyl Ester-Para- Toluenesulfonate
• H-CHA-OME HCL
• Beta-Cyclohexyl-D-Alanine Benzyl Ester Hydrochloride
• 3-CYCLOHEXYL-L-ALANINE AMIDE
• Beta-Cyclohexyl-D-Alanine Benzyl Ester-Para- Toluenesulfonate
• 3-CYCLOHEXYL-D-ALANINE METHYL ESTER HYDROCHLORIDE
• (2S)-2-amino-3-cyclohexylpropanamide:hydrochloride
• (R)OCTAHYDRO-1H-INDOLE-2-CARBOXYLIC ACID
• FMOC-D-CHA-OH
• BOC-D-CHA-OH DCHA
• BOC-D-CHA-OH,BOC-D-CHA-OH H2O,BOC-D-CHA-OH, HYDRATE
• FMOC-L-CHA-OH,FMOC-CHA-OH
• BOC-CHA-OH DCHA,Boc-L-Cha-OH.DCHA
• Z-CHA-OH