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Cas Database

66211-31-2

66211-31-2

Identification

  • Product Name:Glycine, N-[1-[N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl]-L-prolyl]-

  • CAS Number: 66211-31-2

  • EINECS:

  • Molecular Weight:419.478

  • Molecular Formula: C21H29N3O6

  • HS Code:

  • Mol File:66211-31-2.mol

Synonyms:

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 2 Articles be found

Bitter Taste of Synthetic C-Terminal Tetrapeptide of Bovine β-Casein, H-Pro196-Val-Leu-Gly-Pro-Arg-Gly-Pro-Phe-Pro-Ile-Ile-Val209-OH, and Its Related Peptides

Shinoda, Ichizo,Fushimi, Akira,Kato, Hironobu,Okai, Hideo,Fukui, Sazuko

, p. 2587 - 2596 (2007/10/02)

The primary structure of bovine β-casein contains the partial sequence of -Pro196-Val-Leu-Gly-Pro-Val-Arg-Gly-Pro-Phe-Pro-Ile-Ile-Val209 in the C-terminal portion.We previously reported that the synthetic C-terminal octapeptide, Arg202-Val209, is extremly bitter with its threshold value 0.004 mM, 250 times as strong as that of caffeine.To further investigate the bitter taste of the C-terminal portion of β-casein, we synthesized the C-terminal tetrapeptide, Pro196-Val209, and some its fragments.A hydrophobic hexapeptide, Pro196-Val201, was twice as bitter as caffein.The bitter taste of decapeptide, Pro200-Val209, was the same as that of Arg202-Val209.Although the tetradecapeptide, Pro196-Val209, was composed of two bitter peptides, Pro196-Val201 and Arg202-Val209, its bitter taste was weaker than that of Arg202-Val209 and its threshold value was 0.015 mM.We suggested that the increase of bitterness in peptides through the introduction of hydrophobic amino acids depended on the number of hydrophobic amino acids added.In addition, the synthetic retro analog of Arg202-Val209 (H-Val-Ile-Ile-Pro-Phe-Pro-Gly-Arg-OH) was not as bitter as Arg202-Val209.This indicated that the sequence of Arg202-Val209 is important for extreme bitterness.

SYNTHESIS OF 7-β-CASOMORPHINE

Shvachkin, Yu. P.,Krivtsov, V. F.

, p. 410 - 411 (2007/10/02)

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Process route upstream and downstream products

Process route

BOC-phenylalanylprolylglycine benzyl ester
83280-18-6

BOC-phenylalanylprolylglycine benzyl ester

N-tert-butyloxycarbonyl-L-phenylalanyl-L-prolylglycine
66211-31-2

N-tert-butyloxycarbonyl-L-phenylalanyl-L-prolylglycine

Conditions
Conditions Yield
With hydrogen; palladium; In methanol; for 19h;
73%
N-tert-butoxycarbonyl-L-phenylalanyl-L-proline
23420-32-8

N-tert-butoxycarbonyl-L-phenylalanyl-L-proline

N-tert-butyloxycarbonyl-L-phenylalanyl-L-prolylglycine
66211-31-2

N-tert-butyloxycarbonyl-L-phenylalanyl-L-prolylglycine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 97 percent / NMM, ECF / tetrahydrofuran; dimethylformamide / 1 h in ice bath, then room temperature
2: 73 percent / hydrogen / palladium black / methanol / 19 h
With 4-methyl-morpholine; hydrogen; chloroformic acid ethyl ester; palladium; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
tert-butyloxycarbonyl-prolyl-glycine methyl ester
34290-72-7,92132-25-7,1097194-13-2

tert-butyloxycarbonyl-prolyl-glycine methyl ester

N-tert-butyloxycarbonyl-L-phenylalanyl-L-prolylglycine
66211-31-2

N-tert-butyloxycarbonyl-L-phenylalanyl-L-prolylglycine

Conditions
Conditions Yield
N-tert-butyloxycarbonyl-L-prolylglycine
51785-82-1,250290-80-3

N-tert-butyloxycarbonyl-L-prolylglycine

N-tert-butyloxycarbonyl-L-phenylalanyl-L-prolylglycine
66211-31-2

N-tert-butyloxycarbonyl-L-phenylalanyl-L-prolylglycine

Conditions
Conditions Yield
N<sup>G</sup>-nitroarginine benzyl ester
10123-53-2,10342-07-1,65985-34-4,95105-19-4

NG-nitroarginine benzyl ester

N-tert-butyloxycarbonyl-L-phenylalanyl-L-prolylglycine
66211-31-2

N-tert-butyloxycarbonyl-L-phenylalanyl-L-prolylglycine

Boc-Phe-Pro-Gly-Arg(NO<sub>2</sub>)-OBzl
99909-39-4

Boc-Phe-Pro-Gly-Arg(NO2)-OBzl

Conditions
Conditions Yield
With 4-methyl-morpholine; chloroformic acid ethyl ester; In tetrahydrofuran; N,N-dimethyl-formamide; 1 h in ice bath, then room temperature;
71%
N-tert-butyloxycarbonyl-L-phenylalanyl-L-prolylglycine
66211-31-2

N-tert-butyloxycarbonyl-L-phenylalanyl-L-prolylglycine

H-Val-Ile-Pro-Phe-Pro-Gly-Arg-OH*HCl

H-Val-Ile-Pro-Phe-Pro-Gly-Arg-OH*HCl

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: 71 percent / NMM, ECF / tetrahydrofuran; dimethylformamide / 1 h in ice bath, then room temperature
2: 98 percent / 3.5 N HCl / dioxane / 1 h / Ambient temperature
3: NMM, ECF / tetrahydrofuran; dimethylformamide / 1 h in ice bath, then room temperature
4: 80 percent / 98 percent formic acid, 3.5 N hydrogen chloride / dioxane / 0.67 h / 0 °C
5: 62 percent / hydrogen / palladium black / acetic acid / 24 h
With 4-methyl-morpholine; hydrogenchloride; formic acid; hydrogen; chloroformic acid ethyl ester; palladium; In tetrahydrofuran; 1,4-dioxane; acetic acid; N,N-dimethyl-formamide;
N-tert-butyloxycarbonyl-L-phenylalanyl-L-prolylglycine
66211-31-2

N-tert-butyloxycarbonyl-L-phenylalanyl-L-prolylglycine

H-Val-Ile-Ile-Pro-Phe-Pro-Gly-Arg-OH*HCl

H-Val-Ile-Ile-Pro-Phe-Pro-Gly-Arg-OH*HCl

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: 71 percent / NMM, ECF / tetrahydrofuran; dimethylformamide / 1 h in ice bath, then room temperature
2: 98 percent / 3.5 N HCl / dioxane / 1 h / Ambient temperature
3: 51 percent / NMM, ECF / tetrahydrofuran; dimethylformamide / 1 h in ice bath, then room temperature
4: 92 percent / 98 percent formic acid, 3.5 N hydrogen chloride / dioxane / 0.67 h / 0 °C
5: 46 percent / hydrogen / palladium black / acetic acid / 24 h
With 4-methyl-morpholine; hydrogenchloride; formic acid; hydrogen; chloroformic acid ethyl ester; palladium; In tetrahydrofuran; 1,4-dioxane; acetic acid; N,N-dimethyl-formamide;
N-tert-butyloxycarbonyl-L-phenylalanyl-L-prolylglycine
66211-31-2

N-tert-butyloxycarbonyl-L-phenylalanyl-L-prolylglycine

Boc-Val-Ile-Pro-Phe-Pro-Gly-Arg(NO<sub>2</sub>)-OBzl

Boc-Val-Ile-Pro-Phe-Pro-Gly-Arg(NO2)-OBzl

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 71 percent / NMM, ECF / tetrahydrofuran; dimethylformamide / 1 h in ice bath, then room temperature
2: 98 percent / 3.5 N HCl / dioxane / 1 h / Ambient temperature
3: NMM, ECF / tetrahydrofuran; dimethylformamide / 1 h in ice bath, then room temperature
With 4-methyl-morpholine; hydrogenchloride; chloroformic acid ethyl ester; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide;
N-tert-butyloxycarbonyl-L-phenylalanyl-L-prolylglycine
66211-31-2

N-tert-butyloxycarbonyl-L-phenylalanyl-L-prolylglycine

BocVal-Ile-Ile-Pro-Phe-Pro-Gly-Arg(NO<sub>2</sub>)-OBzl

BocVal-Ile-Ile-Pro-Phe-Pro-Gly-Arg(NO2)-OBzl

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 71 percent / NMM, ECF / tetrahydrofuran; dimethylformamide / 1 h in ice bath, then room temperature
2: 98 percent / 3.5 N HCl / dioxane / 1 h / Ambient temperature
3: 51 percent / NMM, ECF / tetrahydrofuran; dimethylformamide / 1 h in ice bath, then room temperature
With 4-methyl-morpholine; hydrogenchloride; chloroformic acid ethyl ester; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide;
N-tert-butyloxycarbonyl-L-phenylalanyl-L-prolylglycine
66211-31-2

N-tert-butyloxycarbonyl-L-phenylalanyl-L-prolylglycine

H-Val-Ile-Pro-Phe-Pro-Gly-Arg(NO<sub>2</sub>)-OBzl*HCl

H-Val-Ile-Pro-Phe-Pro-Gly-Arg(NO2)-OBzl*HCl

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 71 percent / NMM, ECF / tetrahydrofuran; dimethylformamide / 1 h in ice bath, then room temperature
2: 98 percent / 3.5 N HCl / dioxane / 1 h / Ambient temperature
3: NMM, ECF / tetrahydrofuran; dimethylformamide / 1 h in ice bath, then room temperature
4: 80 percent / 98 percent formic acid, 3.5 N hydrogen chloride / dioxane / 0.67 h / 0 °C
With 4-methyl-morpholine; hydrogenchloride; formic acid; chloroformic acid ethyl ester; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide;

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