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L-システイン

L-システイン 化学構造式
52-90-4
CAS番号.
52-90-4
化学名:
L-システイン
别名:
L-システイン;(+)-L-システイン;ハイチオール;チオセリン;システイン;L-(+)-システイン;(R)-2-アミノ-3-メルカプトプロパン酸;(2R)-2-アミノ-3-スルファニルプロパン酸;ハーフシスチン;(R)-システイン;エコラン;ハーフシステイン;(+)-システイン;β-メルカプトアラニン;Lシステイン;L‐システイン;L- システイン;L-システイン (JP17)
英語化学名:
L-Cysteine
英語别名:
CYS;CYSH;E 920;L-Cys;Cystein;NSC-8746;CYSTEINE;H-CYS-OH;L-Cys-OH;FEMA 3263
CBNumber:
CB7388480
化学式:
C3H7NO2S
分子量:
121.16
MOL File:
52-90-4.mol

L-システイン 物理性質

融点 :
220 °C (dec.)(lit.)
比旋光度 :
8.75 º (c=12, 2N HCl)
比重(密度) :
1.197 (estimate)
屈折率 :
8.8 ° (C=8, 1mol/L HCl)
FEMA :
3263 | L-CYSTEINE
貯蔵温度 :
Store at RT.
溶解性:
H2O: 25 mg/mL
酸解離定数(Pka):
1.92(at 25℃)
外見 :
Solid
色:
White
PH:
4.5-5.5 (100g/l, H2O, 20℃)
光学活性 (optical activity):
Optical rotation: +8° to +9° (c = 5, 1 N HCl, 20°C).
水溶解度 :
280 g/L (25 ºC)
Sensitive :
Air Sensitive
極大吸収波長 (λmax):
λ: 260 nm Amax: 1.5
λ: 280 nm Amax: 0.2
Merck :
14,2781
JECFA Number:
1419
BRN :
1721408
安定性::
Stability Stable, but may be air sensitive. Incompatible with oxidizing agents, bases.
CAS データベース:
52-90-4(CAS DataBase Reference)
NISTの化学物質情報:
L-Cysteine(52-90-4)
EPAの化学物質情報:
L-Cysteine(52-90-4)
安全性情報
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  Xn,Xi
Rフレーズ  22-36/37/38-20/21/22
Sフレーズ  36-37/39-26-24/25
WGK Germany  3
RTECS 番号 HA1600000
10-23
自然発火温度 420 °C
TSCA  Yes
HSコード  29309012
有毒物質データの 52-90-4(Hazardous Substances Data)
毒性 LD50 orally in Rabbit: 1890 mg/kg
化審法 (9)-1590 届出不要化学物質
絵表示(GHS)
注意喚起語 Warning
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H302 飲み込むと有害 急性毒性、経口 4 警告 P264, P270, P301+P312, P330, P501
注意書き
P264 取扱い後は皮膚をよく洗うこと。
P264 取扱い後は手や顔をよく洗うこと。
P270 この製品を使用する時に、飲食または喫煙をしないこ と。
P330 口をすすぐこと。

L-システイン 価格 もっと(59)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01APOOR0325 L-システイン
L-Cysteine
52-90-4 100g ¥11000 2018-12-26 購入
富士フイルム和光純薬株式会社(wako) W01APOOR0325 L-システイン
L-Cysteine
52-90-4 250g ¥21500 2018-12-26 購入
東京化成工業 C0515 L-システイン >98.0%(T)
L-Cysteine >98.0%(T)
52-90-4 25g ¥3000 2018-12-04 購入
東京化成工業 C0515 L-システイン >98.0%(T)
L-Cysteine >98.0%(T)
52-90-4 100g ¥7500 2018-12-04 購入
関東化学株式会社(KANTO) 07572-30 L‐システイン >98.0%(T)
L‐Cysteine >98.0%(T)
52-90-4 25g ¥3500 2018-12-13 購入

L-システイン MSDS


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

L-システイン 化学特性,用途語,生産方法

外観

白色、結晶~結晶性粉末

定義

本品は、次の化学式で表されるアミノ酸である。

溶解性

水に溶けやすく、エタノール(99.5)にほとんど溶けない。

用途

SH 基を有する化合物です。 粘液ムコタンパクのジスルフィド結合を解離 する作用を示します。

用途

SH 基を有する化合物です。 粘液ムコタンパクのジスルフィド結合を解離 する作用を示します。

用途

化粧品、食品の添加物、酸化防止剤

化粧品の成分用途

パーマネント.ウェーブ用還元剤、ヘアコンディショニング剤、還元剤、皮膚コンディショニング剤、酸化防止剤

効能

スルフヒドリル酵素活性化薬

使用上の注意

不活性ガス封入

説明

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.

化学的特性

White crystalline powder

天然物の起源

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.

天然物の起源

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.

使用

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.

使用

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.

使用

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.

主な応用

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).

定義

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

生物学の機能

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 .

生物学の機能

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.

副作用

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.

副作用

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.

安全性プロファイル

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

純化方法

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.]

Sheep

Cysteine is required by sheep in order to produce wool: It is an essential amino acid that must be taken in as food from grass. As a consequence, during drought conditions, sheep stop producing wool; however, transgenic sheep that can make their own cysteine have been developed.

L-システイン 上流と下流の製品情報

原材料

準備製品


L-システイン 生産企業

Global( 468)Suppliers
名前 電話番号 ファックス番号 電子メール 国籍 製品カタログ 優位度
Shenzhen Sendi Biotechnology Co.Ltd.
0755-23311925 18102838259
0755-23311925 Abel@chembj.com CHINA 3203 55
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 21968 58
Beijing Cooperate Pharmaceutical Co.,Ltd.
+86-10-60279497 +86(0)15646567669
+86-10-60279497 sales01@cooperate-pharm.com CHINA 1530 55
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20680 55
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32457 55
Nanjing ChemLin Chemical Industry Co., Ltd.
025-83697070;product@chemlin.com.cn
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Jiangsu Qingquan Chemical Co., Ltd.
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ATK CHEMICAL COMPANY LIMITED
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52-90-4(L-システイン)キーワード:


  • 52-90-4
  • L-Alanine, 3-mercapto-
  • L-Amino-thopro-ponicacid
  • L-Mercaptoalanine
  • NSC-8746
  • Propanoic Acid, 2-amino-3-mercapto-, (R)-
  • Thioserine
  • cysteine,b-mercapto-alanine
  • L-CYSTEINE FREE BASE, BIOTECHNOLOGY &
  • L(+)-CYSTEINE BIOSYNTH
  • L-CYSTEINE 97+%
  • L-Cysteine>99%
  • L-CysteineForBiochemistry-(R)-3-Amino-3-MercaptopropionicAcid)
  • L-CysteineForBiochemistry
  • L-CysteineForBiochemistry99+%
  • L-Cysteine,98+%
  • L-CYSTEINE, PHARMA
  • L-Cysteine-1-13C
  • L-CYSTEINUM
  • l-2-amino-3-mercaptopropionic acid
  • (2R)-2-amino-3-sulfanyl-propanoic acid
  • CYTISINE(LABURNIN)(RG)
  • b-Mercaptoalanine
  • E 920
  • L-Cys
  • L-Cysteine (9CI)
  • (+)-2-Amino-3-mercaptopropionic acid
  • L-CYSTEINE extrapure CHR
  • L-Cysteine produced by Wacker Chemie AG, Burghausen, Germany, >=98.0%
  • L-Cysteine Vetec(TM) reagent grade, 97%
  • MAXIMUM RECOVERY DILUENT (ISO)
  • L-システイン
  • (+)-L-システイン
  • ハイチオール
  • チオセリン
  • システイン
  • L-(+)-システイン
  • (R)-2-アミノ-3-メルカプトプロパン酸
  • (2R)-2-アミノ-3-スルファニルプロパン酸
  • ハーフシスチン
  • (R)-システイン
  • エコラン
  • ハーフシステイン
  • (+)-システイン
  • β-メルカプトアラニン
  • Lシステイン
  • L‐システイン
  • L- システイン
  • L-システイン (JP17)
  • α-アミノ酸
  • アミノ酸
  • 抗酸化剤
  • 生化学
  • 代謝産物
  • 代謝作用薬
  • 抗アレルギー薬
  • 血液作用薬
  • 植物成長調整剤
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