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L-시스테인

L-시스테인
L-시스테인 구조식 이미지
카스 번호:
52-90-4
한글명:
L-시스테인
동의어(한글):
L-시스테인;시스테인
상품명:
L-Cysteine
동의어(영문):
CYS;CYSH;E 920;L-Cys;Cystein;NSC-8746;CYSTEINE;H-CYS-OH;L-Cys-OH;FEMA 3263
CBNumber:
CB7388480
분자식:
C3H7NO2S
포뮬러 무게:
121.16
MOL 파일:
52-90-4.mol

L-시스테인 속성

녹는점
220 °C (dec.)(lit.)
알파
8.75 º (c=12, 2N HCl)
밀도
1.197 (estimate)
FEMA
3263 | L-CYSTEINE
굴절률
8.8 ° (C=8, 1mol/L HCl)
저장 조건
Store at RT.
용해도
H2O: 25 mg/mL
산도 계수 (pKa)
1.92(at 25℃)
물리적 상태
Solid
색상
White
수소이온지수(pH)
4.5-5.5 (100g/l, H2O, 20℃)
optical activity
Optical rotation: +8° to +9° (c = 5, 1 N HCl, 20°C).
수용성
280 g/L (25 ºC)
감도
Air Sensitive
최대 파장(λmax)
λ: 260 nm Amax: 1.5
λ: 280 nm Amax: 0.2
JECFA Number
1419
Merck
14,2781
BRN
1721408
안정성
Stability Stable, but may be air sensitive. Incompatible with oxidizing agents, bases.
CAS 데이터베이스
52-90-4(CAS DataBase Reference)
NIST
L-Cysteine(52-90-4)
EPA
L-Cysteine(52-90-4)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xn,Xi
위험 카페고리 넘버 22-36/37/38-20/21/22
안전지침서 36-37/39-26-24/25
WGK 독일 3
RTECS 번호 HA1600000
F 고인화성물질 10-23
자연 발화 온도 420 °C
TSCA Yes
HS 번호 29309012
유해 물질 데이터 52-90-4(Hazardous Substances Data)
독성 LD50 orally in Rabbit: 1890 mg/kg
그림문자(GHS):
신호 어: Warning
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H302 삼키면 유해함 급성 독성 물질 - 경구 구분 4 경고 P264, P270, P301+P312, P330, P501
예방조치문구:
P264 취급 후에는 손을 철저히 씻으시오.
P264 취급 후에는 손을 철저히 씻으시오.
P270 이 제품을 사용할 때에는 먹거나, 마시거나 흡연하지 마시오.
P330 입을 씻어내시오.

L-시스테인 MSDS


(+)-2-Amino-3-mercaptopropionic acid

L-시스테인 C화학적 특성, 용도, 생산

개요

Cysteine (abbreviated as Cys or C) is an α-amino acid with the chemical formula HO2CCH(NH2)CH2SH. It is a semi - essential amino acid, which means that it can be biosynthesized in humans. The thiol side chain in cysteine often participates in enzymatic reactions, serving as a nucleophile. The thiol is susceptible to oxidization to give the disulfide derivative cystine, which serves an important structural role in many proteins. When used as a food additive, it has the E number E920.

화학적 성질

White crystalline powder

출처

Dietary sources
Although classified as a non-essential amino acid, in rare cases, cysteine may be essential for infants, the elderly, and individuals with certain metabolic disease or who suffer from malabsorption syndromes. Cysteine can usually be synthesized by the human body under normal physiological conditions if a sufficient quantity of methionine is available.
Cysteine is catabolized in the gastrointestinal tract and blood plasma. In contrast, cystine travels safely through the GI tract and blood plasma and is promptly reduced to the two cysteine molecules upon cell entry.
Industrial sources
The majority of L - cysteine is obtained industrially by hydrolysis of poultry feathers or human hair. Synthetically produced L-cysteine, compliant with Jewish Kosher and Muslim Halal rules, is also available, albeit at a higher price. The synthetic route involves fermentation utilizing a mutant of E. coli.
Biosynthesis
In animals, biosynthesis begins with the amino acid serine. The sulfur is derived from methionine, which is converted to homocysteine through the intermediate S- adenosylmethionine. Cystathionine betasynthase then combines homocysteine and serine to form the asymmetrical thioether cystathionine. The enzyme cystathionine gamma-lyase converts the cystathionine into cysteine and alphaketobutyrate.

출처

Dietary sources
Although classified as a non - essential amino acid, in rare cases, cysteine may be essential for infants, the elderly, and individuals with certain metabolic disease or who suffer from malabsorption syndromes. Cysteine can usually be synthesized by the human body under normal physiological conditions if a sufficient quantity of methionine is available. Cysteine is catabolized in the gastrointestinal tract and blood plasma . In contrast, cystine travels safely through the GI tract and blood plasma and is promptly reduced to the two cysteine molecules upon cell entry.
Cysteine is found in most high-protein foods, including :
Animal sources: pork, sausage meat, chicken, turkey, duck, luncheon meat, eggs, milk, whey protein, ricotta, cottage cheese, yogurt
Plant sources: red peppers, garlic, onions, broccoli, brussels sprout, oats, granola, wheat germ, sprouted lentils. Like other amino acids, cysteine has an amphoteric character.
Industrial sources
The majority of L-cysteine is obtained industrially by hydrolysis of poultry feathers or human hair. Synthetically produced L-cysteine, compliant with Jewish Kosher and Muslim Halal rules, is also available, albeit at a higher price . The synthetic route involves fermentation utilizing a mutant of E. coli. Degussa introduced a route from substituted thiazolines. Following this technology, L-cysteine is produced by the hydrolysis of racemic 2-amino-Δ22-thiazoline-4- carboxylic acid using Pseudomonas thiazolinophilum.
BiosynthesisIn animals, biosynthesis begins with the amino acid serine. The sulfur is derived from methionine, which is converted to homocysteine through the intermediate S- adenosylmethionine. Cystathionine betasynthase then combines homocysteine and serine to form the asymmetrical thioether cystathionine. The enzyme cystathionine gamma-lyase converts the cystathionine into cysteine and alphaketobutyrate. In plants and bacteria, cysteine biosynthesis again starts from serine, which is converted to O-acetylserine by the enzyme serine transacetylase. The enzyme O-acetylserine (thiol)-lyase, using sulfide sources, converts this ester into cysteine, releasing acetate.

용도

L-Cysteine is a non-essential amino acid that can be synthesized by the human body under normal physiological conditions if a sufficient quantity of methionine is available. L-Cysteine is commonly use d as a precursor in the food and pharmaceutical industries. L-Cysteine is used as a processing aid for baking, as an additive in cigarettes, as well as in the preparation of meat flavours.

용도

cysteine is an essential amino acid obtained by fermentation. Cysteine is a component of the skin’s natural moisturizing factor and can help normalize oil gland secretion because of its sulfur content. It is also said to promote wound healing. In addition, studies indicate that cysteine helps increase levels of glutathione (an anti-oxidant) in the body. It is considered beneficial in treating oily skin.

용도

Cysteine is a nonessential amino acid that functions as a nutrient and dietary supplement. It is used in foods to prevent oxygen from destroying vitamin c and is used in doughs to reduce mixing time.

정의

ChEBI: An optically active form of cysteine having L-configuration.

주요 응용

Cysteine, mainly the L-enantiomer, is a precursor in the food, pharmaceutical, and personal care industries. One of the largest applications is the production of flavors. For example, the reaction of cysteine with sugars in a Maillard reaction yields meat flavors. Lcysteine is also used as a processing aid for baking.
In the field of personal care, cysteine is used for permanent wave applications predominantly in Asia. Again the cysteine is used for breaking up the disulfide bonds in the hair's keratin.
Cysteine is a very popular target for site-directed labeling experiments to investigate biomolecular structure and dynamics. Maleimides will selectively attach to cysteine using a covalent Michael addition. Site- directed spin labeling for EPR or paramagnetic relaxation enhanced NMR also uses cysteine extensively.
In a 1994 report released by five top cigarette companies, cysteine is one of the 599 additives to cigarettes. Like most cigarette additives, however, its use or purpose is unknown. Its inclusion in cigarettes could offer two benefits: Acting as an expectorant, since smoking increases mucus production in the lungs; and increasing the beneficial antioxidant glutathione (which is diminished in smokers).

Biological Functions

The cysteine thiol group is nucleophilic and easily oxidized. The reactivity is enhanced when the thiol is ionized, and cysteine residues in proteins have pKa values close to neutrality, so are often in their reactive thiolate form in the cell. Because of its high reactivity, the thiol group of cysteine has numerous biological functions.
Precursor to the antioxidant glutathione
Due to the ability of thiols to undergo redox reactions, cysteine has antioxidant properties. Cysteine's antioxidant properties are typically expressed in the tripeptide glutathione, which occurs in humans as well as other organisms.
Precursor to iron-sulfur clusters
Cysteine is an important source of sulfide in human metabolism. The sulfide in iron-sulfur clusters and in nitrogenase is extracted from cysteine, which is converted to alanine in the process.
Metal ion binding
Beyond the iron - sulfur proteins, many other metal cofactors in enzymes are bound to the thiolate substituent of cysteinyl residues. Examples include zinc in zinc fingers and alcohol dehydrogenase, copper in the blue copper proteins, iron in cytochrome P450, and nickel in the [NiFe]-hydrogenases . The thiol group also has a high affinity for heavy metals, so that proteins containing cysteine, such as metallothionein, will bind metals such as mercury, lead, and cadmium tightly.
Roles in protein structure
In the translation of messenger RNA molecules to produce polypeptides, cysteine is coded for by the UGU and UGC codons. Cysteine has traditionally been considered to be a hydrophilic amino acid, based largely on the chemical parallel between its thiol group and the hydroxyl groups in the side-chains of other polar amino acids. However, the cysteine side chain has been shown to stabilize hydrophobic interactions in micelles to a greater degree than the side chain in the non-polar amino acid glycine, and the polar amino acid serine .

Biological Functions

The cysteine thiol group is nucleophilic and easily oxidized. The reactivity is enhanced when the thiol is ionized, and cysteine residues in proteins have pKa values close to neutrality, so are often in their reactive thiolate form in the cell. Because of its high reactivity, the thiol group of cysteine has numerous biological functions.
1-Precursor to the antioxidant glutathione
2-Precursor to iron-sulfur clusters
3-Metal ion binding
4-Roles in protein structure.

부작용

Cysteine has been proposed as a preventative or antidote for some of the negative effects of alcohol, including liver damage and hangover. It counteracts the poisonous effects of acetaldehyde, which is the major by - product of alcohol metabolism and is responsible for most of the negative aftereffects and long - term damage associated with alcohol use (but not the immediate effects of drunkenness). Cysteine supports the next step in metabolism, which turns acetaldehyde into the relatively harmless acetic acid. In a rat study, test animals received an LD50 dose of acetaldehyde. Those that received cysteine had an 80 % survival rate; when both cysteine and thiamine were administered, all animals survived . There is not yet direct evidence for or against its effectiveness in humans who consume alcohol at normal levels.
N-Acetylcysteine
N - Acetyl - L - cysteine (NAC) is a derivative of cysteine wherein an acetyl group is attached to the nitrogen atom. This compound is sold as a dietary supplement and used as an antidote in cases of acetaminophen overdose, and obsessive compulsive disorders such as trichotillomania.

부작용

Cysteine has been proposed as a preventative or antidote for some of the negative effects of alcohol, including liver damage and hangover. It counteracts the poisonous effects of acetaldehyde, which is the major by-product of alcohol metabolism and is responsible for most of the negative aftereffects and long-term damage associated with alcohol use (but not the immediate effects of drunkenness). Cysteine supports the next step in metabolism, which turns acetaldehyde into the relatively harmless acetic acid. In a rat study, test animals received anLD50 dose of acetaldehyde. Those that received cysteine had an 80 % survival rate; when both cysteine and thiamine were administered, all animals survived. There is not yet direct evidence for or against its effectiveness in humans who consume alcohol at normal levels.
N-Acetylcysteine
N-Acetyl-L-cysteine (NAC) is a derivative of cysteine wherein an acetyl group is attached to the nitrogen atom. This compound is sold as a dietary supplement and used as an antidote in cases of acetaminophen overdose, and obsessive compulsive disorders such as trichotillomania.

특성

무색∼흰색의 결정 또는 흰백색의 결정성 가루로 특이한 냄새와 맛이 있다. 물에 녹으며 메탄올에 잘 용해되나 에테르에 용해되지 않는다.

Safety Profile

Moderately toxic by ingestion, intraperitoneal, and subcutaneous routes. Experimental reproductive effects. Human mutation data reported. When heated to decomposition fumes of SO and NO.

성질

L-시스틴과 달리 물, 에탄올에 녹는다. 니트로프루시드 반응, 설리반 반응 등 양성. 수은, 구리 등과 불용성의 염을 만든다. 중성 또는 약한 알칼리성으로 철 또는 구리 이온의 존재에서 공기에 의해 L-시스틴으로 산화되고 브롬에서는 더욱 산화된 L-시스테산을 생성한다. 알칼리성 용액 중에서는 매우 불안정하여 황화수소, 암모니아를 발생하여 피루브산을 생성한다. 염산의 존재에서 알데히드, 케톤류와 축합하여 상당하는 티오아세탈, 케톤티오아세탈을 생성하고 중성에서 가열한 경우에는 티아졸리딘 유도체가 된다.

용도

산화방지제, 착향제, 퍼머넌트웨이브용제/헤어스트레이트너용제, 헤어

Purification Methods

Purify it by recrystallisation from H2O (free from metal ions) and dry it in a vacuum. It is soluble in H2O, EtOH, Me2CO, EtOAc, AcOH, *C6H6 and CS2. Acidic solutions can be stored under N2 for a few days without deterioration. [For synthesis and spectra see Greenstein & Winitz Chemistry of the Amino Acids (J. Wiley) Vol 3 p1879 1961, Beilstein 4 III 1618, 4 IV 3144.]

L-시스테인 준비 용품 및 원자재

원자재

준비 용품


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