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D-cycloserine
Cas No: 68-41-7
No Data 1 Metric Ton 100 Kilogram/Day Hangzhou Benoy Chemical Co.,Ltd Contact Supplier
D-Cycloserine Manufacturer/High quality/Best price/In stock
Cas No: 68-41-7
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
High purity Various Specifications D-cycloserine CAS:68-41-7
Cas No: 68-41-7
USD $ 100.0-500.0 / Gram 1 Gram 99999 Gram/Year Hangzhou Dingyan Chem Co., Ltd Contact Supplier
High quality D-Cycloserine supplier in China
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No Data 1 Metric Ton 30 Metric Ton/Month Simagchem Corporation Contact Supplier
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Cas No: 68-41-7
USD $ 1.0-10.0 / Kilogram 1 Kilogram 5000 Kilogram/Month WUHAN MULEI NEW MATERIAL CO., LTD Contact Supplier
high purity D-cycloserine CAS NO.68-41-7
Cas No: 68-41-7
USD $ 1.0-3.0 / Metric Ton 1 Metric Ton 10 Metric Ton/Day Hebei yanxi chemical co.,LTD. Contact Supplier
D-cycloserine CAS No.68-41-7
Cas No: 68-41-7
No Data 1 Gram 1000 Kilogram/Month Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd Contact Supplier
D-cycloserine
Cas No: 68-41-7
No Data 1 Kilogram Metric Ton/Day Hefei TNJ chemical industry co.,ltd Contact Supplier
High quality D-cycloserine 99% with lower price
Cas No: 68-41-7
USD $ 520.0-550.0 / Kilogram 1 Kilogram 3000 Kilogram/Month Kono Chem Co.,Ltd Contact Supplier
Hot Sale Tuberculostatics USP Standard 99% CAS 68-41-7 D-Cycloserine Powder
Cas No: 68-41-7
USD $ 1.1-1.3 / Gram 100 Gram 5000 Kilogram/Month Xi'an Julong Bio-Tech Co., Ltd. Contact Supplier

68-41-7 Usage

Uses

antibacterial (tuberculostatic)

Brand name

Seromycin (Lilly).

Production process

D-Cycloserine can be obtained through fermentation technique or through direct synthesis. The bacteria used in the fermentation is Actinomyces laven-dulae. The fermentation medium consists of dextrin, dextrose, starch, soybean powder, yeast powder, ammonium sulfate, ammonium nitrate, calcium carbonate, sodium chloride, magnesium sulfate and soybean oil. In the synthesis process, D-cycloserine is obtained from β-aminooxy alanine ethyl ester hydrochloride by reaction with potassium hydroxide in a cyclization reaction.

Purification Methods

Purify cycloserine by recrystallisation from aqueous EtOH or MeOH or aqueous NH3/EtOH or isoPrOH. Also recrystallise it from aqueous ammoniacal solution at pH 10.5 (100mg/mL) by diluting with 5 volumes of isopropanol and then adjusting to pH 6 with acetic acid. An aqueous solution, buffered to pH 10 with Na2CO3, can be stored in a refrigerator for 1week without decomposition. UV: max at 226nm (A1cm 1% 4.02). The tartrate salt has m 165-166o (dec), 166-168o (dec), and [] D 24 -41o (c 0.7, H2O). [Stammer et al. J Am Chem Soc 79 3236 1959, UV: Kuehl J Am Chem Soc 77 2344 1955, Beilstein 27 III/IV 5549.]

Chemical properties

Colorless needle or leafy crystals, or amorphous powder; melting point 155-156℃ (decomposition). Soluble in water; slightly soluble in methanol, ethanol, butanol, propylene glycol, isopropyl alcohol and acetone; and hardly soluble or insoluble in toluene, chloroform, ether, pyridine, benzene and carbon disulfide.

Uses

D-Cycloserine inhibits cell wall biosynthesis (D-Ala peptide bond formation). D-Cycloserine also prevents conversion of D-Ala to L-Ala. D-Cycloserine is an bacteriostatic. D-Cycloserine is an antibiot ic against Gram-negative bacteria.

Chemical Properties

White to pale yellow cryst. powder

Uses

Used as an antibiotic medicine in the treatment of drug-resistant Mycobacterium tuberculosis infection.
Biochemical research

A second-line anti-TB drug

D-cycloserine is a broad-spectrum polypeptide antibiotic produced by Streptomyces lavendulae and Streptomyces orchidaceus or synthesized by chemical methods. As white crystals with strong hygroscopic nature, it is soluble in water, slightly soluble in lower alcohols, acetone and dioxane, and hardly soluble in chloroform and petroleum ether. It is relatively stable in alkaline solution and decomposes rapidly in acidic or neutral solutions. As a broad-spectrum antibiotic, cycloserine is inhibitive against most Gram-positive and Gram-negative bacteria, rickettsia and some protozoa, with the exception of Mycobacterium tuberculosis., It is also effective on some of the Mycobacterium tuberculosis strains with tolerance to streptomycin, vinactane para-aminosalicylic acid, isoniazid and pyrazinamide. Cycloserine slightly synergizes with isoniazid in the inhibition of Mycobacterium tuberculosis H37RV, but it neither synergizes nor antagonizes against streptomycin. The product is a bacteriostatic agent, and thus won’t exert bactericidal effect even when increasing the dose or prolonging the action time with bacteria.
The Mechanism of D-cycloserine’s antibacterial action is to inhibit the biosynthesis of peptidoglycan of the cell wall. As it is a structural analog of D-alanine, D-cycloserine can competitively inhibit the activities of alanine racemase and D-alanyl-D-alanine synthetase, which are two important enzymes in peptidoglycan synthesis. D-cycloserine shows weak inhibitive activity against Mycobacterium tuberculosis which is only 1/10 to 1/20 that of streptomycin. The advantage of the product is that it is effective on drug-resistant Mycobacterium tuberculosis strains and less likely to induce drug resistance. The product can be used with other anti-tuberculosis drugs in the treatment of tuberculosis caused by drug-resistant Mycobacterium tuberculosis.
Cycloserine is a second-line anti-tuberculosis drug. It can inhibit the growth of Mycobacterium tuberculosis, but the effect is relatively weaker than that of the first-line drugs. Its efficacy in tuberculosis treatment is relatively low. Use the drug alone may produce drug resistance, but the resistance occurs slowly compared with that of other anti-tuberculosis drugs. No cross-resistance has been found between cycloserine and other anti-tuberculosis drugs. The mechanism of its antibacterial action is to inhibit the synthesis of peptidoglycan of bacterial cell wall, causing defective in cell wall architecture. The main structural component of the bacterial cell wall is peptidoglycan, which is composed of N-acetylglucosamine (GNAc) and N-acetylmuramic acid (MNAc). N-acetylmuramic acid is linked with pentapeptide and connects N-acetylglucosamine in a reduplicated and alternative manner. The formation of cytoplasmic peptidoglycan precursor may be hampered by cycloserine, as the latter can hinder the racemase and the synthetase of D-alanine, and thus blocks the formation of N-acetylmuramic acid.
InChI:InChI=1/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/p+1/t2-/m1/s1

68-41-7 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
USP (1158005)  Cycloserine  United States Pharmacopeia (USP) Reference Standard 68-41-7 1158005-250MG 4,662.45CNY Detail
Alfa Aesar (A18000)  D-Cycloserine, 98+%    68-41-7 5g 2343.0CNY Detail
Alfa Aesar (A18000)  D-Cycloserine, 98+%    68-41-7 1g 720.0CNY Detail
TCI America (C1189)  D-(+)-Cycloserine  >98.0%(HPLC)(T) 68-41-7 5g 1,690.00CNY Detail
TCI America (C1189)  D-(+)-Cycloserine  >98.0%(HPLC)(T) 68-41-7 1g 520.00CNY Detail

68-41-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-Isoxazolidinone,4-amino-, (4R)-

1.2 Other means of identification

Product number -
Other names D-Cycloserine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:68-41-7 SDS

68-41-7Synthetic route

Methyl (2R)-2-amino-3-chloropropionate hydrochloride
17136-54-8

Methyl (2R)-2-amino-3-chloropropionate hydrochloride

cycloserine
68-41-7

cycloserine

Conditions
ConditionsYield
With hydrogenchloride; acetone oxime In methanol at 65℃; for 1h; Temperature;94.25%
methyl (2R)-2-amino-3-(aminooxy)propanoate
29491-80-3

methyl (2R)-2-amino-3-(aminooxy)propanoate

cycloserine
68-41-7

cycloserine

Conditions
ConditionsYield
Stage #1: methyl (2R)-2-amino-3-(aminooxy)propanoate With sodium hydroxide In water at -5 - 0℃; for 3h;
Stage #2: With acetic acid In water; isopropyl alcohol at -12 - -8℃; for 1h; pH=6.7 - 6.9;
80%
BrH*C4H8BrNO2
1360187-62-7

BrH*C4H8BrNO2

A

2-aminoacrylic acid methyl ester

2-aminoacrylic acid methyl ester

B

cycloserine
68-41-7

cycloserine

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium hydroxide In methanol; water at 0 - 20℃; for 5h;A 66%
B 27%
With hydroxylamine hydrochloride; sodium methylate In methanol; water at 0 - 20℃; for 9h;A 39%
B 48%
D-cycloserine-L-tartrate
72270-01-0

D-cycloserine-L-tartrate

cycloserine
68-41-7

cycloserine

Conditions
ConditionsYield
With Amberlite IR-120 PLUS ion exchange resin (sodium form) In water Inert atmosphere;65%
D-2-amino-3-chloropropionic acid chloride hydrochloride
121362-14-9

D-2-amino-3-chloropropionic acid chloride hydrochloride

cycloserine
68-41-7

cycloserine

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium hydroxide In water; toluene at -5 - 30℃; pH=11 - 12; pH-value;58.1%
D-2-amino-3-chloropropionohydroxamic acid hydrochloride
120883-74-1

D-2-amino-3-chloropropionohydroxamic acid hydrochloride

cycloserine
68-41-7

cycloserine

Conditions
ConditionsYield
With sodium hydroxide In water at 25℃; pH=11; Cooling;50%
3-chloro-D-alanine hydroxyamide
23628-35-5

3-chloro-D-alanine hydroxyamide

cycloserine
68-41-7

cycloserine

Conditions
ConditionsYield
With water; triethylamine

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