L-Cysteine L-半胱氨酸

CAS 52-90-4 MFCD00064306

化学结构图

52-90-4
SMILES: N[C@@H](CS)C(=O)O

化学属性

Mol. FormulaC3H7NO2S
Mol. Weight121.16
Melting Point220°C
TSCAYes
Density1.334
Stability对光和空气敏感
Appearance 氨基酸之一，但属非必须氨基酸。 无色至白色细柱状结晶或白色结晶性粉末，有轻微特殊气味和滋味(略酸)。具还原性，有抗氧和防止非酶性褐变作用。熔点175℃(分解)。溶于水，水溶液呈酸性，pH值在3%时为1.2，1%时为1.7，0.1%时为2.4。亦溶于乙醇、氨水和醋酸，不溶于乙醚、丙酮、苯、二硫化碳和氯仿。
SolubilitySoluble in water (10 mg/ml), 1N HCl (50 mg/ml), and ethanol.
Refractive index8.8 ° (C=8, 1mol/L HCl)
Boiling Point293.9°C at 760 mmHg

别名和识别编码

Chemical NameL-Cysteine
Synonym L-Cysteine {LY} L-Cysteine {} {LY} L-Cysteine {} {} {LY} L-Cysteine {} {} {} {LY} L-Cysteine {} {} {} {} {LY} L-Cysteine {} {} {} {} {} {LY} L-Cysteine {} {} {} {} {} {} {LY} L-Cysteine {} {} {} {} {} {} {} {LY} L-Cysteine {} {} {} {} {} {} {} {} {LY} L-Cysteine {} {} {} {} {} {} {} {} {} {LY} L-Cysteine {} {} {} {} {} {} {} {} {} {} {LY} L-Cysteine {} {} {} {} {} {} {} {} {} {} {} {LY} L-Cysteine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Cysteine {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Cysteine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Cysteine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Cysteine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Cysteine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Cysteine {} {} {} {} {} {} {} {} {} {} {} {} {}
Beilstein Registry Number1721408
CAS Number52-90-4
EC Number200-158-2
MDL NumberMFCD00064306
PubChem Substance ID87565632
Merck Number2781
Chemical Name TranslationL-半胱氨酸
Reaxys-RN1721408
Wiswesser Line NotationQVYZ1SH
LabNetwork Molecule IDLN00196288
InChIInChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1
Canonical SMILESN[C@@H](CS)C(O)=O
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分类

  • {SNA} Alphabetical Listings, C-D, Flavors and Fragrances
  • {SNA} A-F, All Alphabetically Sorted, Amino Acids, Analytical Standards, Analytical/Chromatography, Certified Reference Materials (CRMs), Chromatography, E numbers (Food Additives), E900–E999 (miscellaneous), E920, Flavors and Fragrances, Fluka CRM for chromatography (neats), Food & Beverage Standards, Organic CRMs Alphabetical, Organic C
  • {SNA} Amines, Building Blocks, C2 to C5, Chemical Synthesis, Nitrogen Compounds, Organic Building Blocks, Sulfur Compounds, Thiols/Mercaptans

产品应用

  • A non-essential amino acid.

相关文献及参考

  • Arakawa, T. and Timasheff, S.N., Theory of protein solubility. Meth. Enzymol. 114 , 49, (1985)
  • Beilstein:4,506
  • Parsons, R.B., et al., In vitro effect of the cysteine metabolites homocysteic acid, homocysteine and cysteic acid upon human neuronal cell lines. Neurotoxicology 19 , 599-603, (1998) 摘要
  • Short: EINECS
  • Short: III/10a
  • [1]. McGavigan AK, et al. L-cysteine suppresses ghrelin and reduces appetite in rodents and humans. Int J Obes (Lond). 2015 Mar;39(3):447-55.

安全信息

RTECSHA1600000
GHS Symbol
Signal word Warning
Hazard statements
  • H302 Harmful if swallowed 吞食有害
WGK Germany1
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes Xn Xn,Xi
Safety Statements
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触；
Risk Statements
  • R22 Harmful if swallowed 吞咽有害
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Storage condition 2-8°C {LY} 2-8°C Air Sensitive Store at RT. {} {LY} 2-8°C {} {} {LY} 2-8°C {} {} {} {LY} 2-8°C {} {} {} {} {LY} 2-8°C {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY}
Precautionary statements
  • P262 Do not get in eyes, on skin, or on clothing. 不要接触眼睛，皮肤或衣服。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西，喝水或吸烟。
  • P301+P312+P330
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 1550 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Behavioral - ataxia
   Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
   OYYAA2 Oyo Yakuri.  Pharmacometrics.  (Oyo Yakuri Kenkyukai, CPO Box 180,
   Sendai 980-91, Japan) V.1-    1967-  Volume(issue)/page/year: 7,1251,1973

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1400 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Behavioral - ataxia
   Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
   OYYAA2 Oyo Yakuri.  Pharmacometrics.  (Oyo Yakuri Kenkyukai, CPO Box 180,
   Sendai 980-91, Japan) V.1-    1967-  Volume(issue)/page/year: 7,1251,1973

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 1890 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Lungs, Thorax, or Respiration - dyspnea
   Kidney, Ureter, Bladder - other changes in urine composition
REFERENCE :
   AGACBH Agents and Actions, A Swiss Journal of Pharmacology.  (Birkhaeuser
   Verlag, POB 133, CH-4010 Basel, Switzerland)  V.1-    1969/70-
   Volume(issue)/page/year: 4,125,1974

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1360 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Behavioral - ataxia
   Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
   OYYAA2 Oyo Yakuri.

T

TYPE OF TEST            : Sister chromatid exchange
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 10 mg/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 372,75,1996

TYPE OF TEST            : Unscheduled DNA synthesis
TEST SYSTEM             : Human Fibroblast
DOSE/DURATION           : 1 mmol/L
REFERENCE :
   CALEDQ Cancer Letters (Shannon, Ireland).  (Elsevier Scientific Pub. Ireland
   Ltd., POB 85, Limerick, Ireland)

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Microorganism - not otherwise specified
DOSE/DURATION           : 25 mmol/plate
REFERENCE :
   BZARAZ Biologicheskii Zhurnal Armenii.  Biological Journal of Armenia. (V/O
   Mezhdunarodnaya Kniga, 113095 Moscow, USSR)  V.19-    1966-
   Volume(issue)/page/year: 32,1146,1979

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Rodent - rat Liver
DOSE/DURATION           : 1 mmol/L
REFERENCE :
   ABBIA4 Archives of Biochemistry and Biophysics.  (Academic Press, Inc., 1 E.
   First St., Duluth, MN 55802)  V.31-    1951-  Volume(issue)/page/year:
   166,400,1975

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Escherichia coli
DOSE/DURATION           : 25 mmol/plate
REFERENCE :
   BZARAZ Biologicheskii Zhurnal Armenii.  Biological Journal of Armenia. (V/O
   Mezhdunarodnaya Kniga, 113095 Moscow, USSR)  V.19-    1966-
   Volume(issue)/page/year: 32,1146,1979

TYPE OF TEST            : Cytogenetic analysis
TEST SYSTEM             : Rodent - hamster Ovary
DOSE/DURATION           : 1 mmol/L
REFERENCE :
   CALEDQ Cancer Letters (Shannon, Ireland).  (Elsevier Scientific Pub. Ireland
   Ltd., POB 85, Limerick, Ireland)  V.1-    1975- Volume(issue)/page/year:
   5,199,1978

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 6 gm/kg
SEX/DURATION            : male 30 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland,
   accessory glands
REFERENCE :
   OYYAA2 Oyo Yakuri.  Pharmacometrics.  (Oyo Yakuri Kenkyukai, CPO Box 180,
   Sendai 980-91, Japan) V.1-    1967-  Volume(issue)/page/year: 7,1251,1973

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 100 mg/kg
SEX/DURATION            : female 12 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured
   before birth)
REFERENCE :
   PSEBAA Proceedings of the Society for Experimental Biology and Medicine.
   (Academic Press, Inc., 1 E. First St., Duluth, MN 55802)  V.1-    1903/04-
   Volume(issue)/page/year: 139,62,1972

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 27600 mg/kg
SEX/DURATION            : female 23 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Maternal Effects - menstrual cycle changes or disorders
REFERENCE :
   ENDOAO Endocrinology (Baltimore).  (Williams & Wilkins Co., 428 E. Preston
   St., Baltimore, MD 21203) V.1-    1917-  Volume(issue)/page/year:
   69,331,1961

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 3600 mg/kg
SEX/DURATION            : female 7-12 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Newborn - physical
REFERENCE :
   TOIZAG Toho Igakkai Zasshi.  Journal of Medical S

其他信息

  • 生理功能与作用:半胱氨酸能帮助机体解毒。它与硒及维生素E一起是最好的自由基清除剂。半胱氨酸也是谷胱甘肽的前体，谷胱甘肽在肝中能与有害物质结合并解毒。它能保护肝脏与大脑免受香烟、酒精与药物的损害。 由于半胱氨酸比胱氨酸更容易溶解，所以更容易被身体所利用来治疗各种疾病。在体内半胱氨酸合成中维生素B6是必需的。有慢性疾病时半胱氨酸便不能合成，因此有慢性疾病的人需要更高剂量的半胱氨酸，例如每日3次，每次1g，持续1个月。 在患风湿性关节炎、血管硬化与癌症时需要补充半胱氨酸。半胱氨酸还能在手术及烧伤后加速痊愈，与重金属络合，并能帮助铁的吸收。这两种氨基酸还能加速脂肪的利用与肌肉的形成。半胱氨酸能清除呼吸道中的粘液，因此它能治疗支气管炎、肺气肿与肺结核。 半胱氨酸 (或与乙酰结合的乙酰半胱氨酸) 服用后，
  • 用途四:面包改良剂；营养增补剂；抗氧化剂；护色剂。对丙烯腈和芳香族酸中毒有解毒作用；有预防放射线损伤作用；有治疗支气管炎和化痰作用；有吸收酒精，将其在体内转化为乙醛的解醉
  • MSDS 信息:(+)-2-Amino-3-mercaptopropionic acid(52-90-4).msds
  • 制备方法:半胱氨酸可用三种方法制取方法： 1，提取法：是将毛发(或羽毛粉)加工成胱氨酸后，溶在盐酸中，然后电解或用锡与盐酸还原而制得L-半胱氨酸盐酸盐。 2，合成法：目前工业上应用的有β-氯丙氨酸法、α-溴丙烯酸甲酯法与Degussa法。 以α-氯丙烯酸甲酯和硫脲为原料，先合成DL-2-氨基噻唑啉-4-羧酸，然后在嗜噻唑假单胞菌菌体酶的作用下，进行不对称水解，可制得。 以α-溴丙烯酸甲酯为原料，与甲基硫代乙酰胺反应，得到2-甲基噻唑啉-4-羧酸甲酯，再水解，可制得。 以氯乙醛为原料，与硫酸氢钠反应，生成α-羟基-β-氯乙醇磺酸钠[2]，[2]与氢氧化铵反应，生成α-氨基-β-氯磺酸钠[3]，[3] 与氢化钠反应得到α-氨基-β-氯丙腈[4]，[4]水解后，得到β-氯丙氨酸[5]，[5]与硫代硫酸铵反应，再水解，可得到DL-半胱氨酸沉淀，然后脱盐，可制得L-半胱氨酸。 3，酶法(味之素法)：是以α-氯丙烯酸甲酯和硫脲为原料，先合成DL-2-氨基噻唑啉-4-羧酸(DL-ATC)，然后在嗜噻唑假单胞菌菌体三种酶的作用下发生不对称水解，生成L-半胱氨酸。
  • 无色结晶。其中性或微碱性水溶液能被空气氧化成胱氨酸，酸性溶液较为稳定。水中溶解度:280 g/L (25°C)，溶于醇，不溶于乙醚、苯、丙酮、乙酸乙酯、二硫化碳和四氯化碳。有刺激 [α]20D 8.8 ° (C=8.00, 1mol/L HCl)
  • 方法三:1.锡粒还原法 将胱氨酸溶于稀盐酸中，过滤，滤液加入锡粒升温回流2h。将还原液用水稀释，移去剩余锡粒，通入硫化氢使饱和，过滤，滤渣用少量水洗，将洗、滤液合并，减压浓缩，冷却结晶，过滤、干燥得L-半胱氨酸盐酸盐。2.电解还原法 将蒸馏水、盐酸、胱氨酸加入电解槽搅拌溶解，维持在50℃以下电解至终点。将所得电解液通硫化氢数小时，过滤。滤液加活性炭脱色，过滤后减压浓缩，冷却结晶，过滤，干燥，得L-半胱氨酸盐酸盐。
  • 图谱信息:L-半胱氨酸(52-90-4)核磁图( 13 CNMR) L-半胱氨酸(52-90-4)红外图
  • 参考质量标准:含量不少于99.5%；比旋光度[α] 20 D +7°-+8.8°；氯化物(以Cl计)含量小于0.04%，硫酸盐(以SO 2- 4 计)含量小于0.03%，重金属(以Pb计)含量小于0.001%，氨含量小于0.02%；标准品高效液相色谱呈单峰。
  • 用途五:主要用于医药、化妆品、生化研究等方面。用于面包料中，以促进谷朊形成及促进发酵、出模、防止老化等。用于天然果汁中，以防止维生素C氧化和防止果汁变成褐色。该品有解毒作用，可用于丙烯腈中毒、芳香族酸中毒。该品还有预防放射线损伤人体的作用，也是治疗支气管炎的药物，尤其是作为化痰药（大多以乙酰L-半胱氨酸甲酯酸盐的形式使用。化妆品方面主要用于美容水、烫发液、防日晒的护肤膏霜等。
  • 其中性或微碱性水溶液能被空气氧化成胱氨酸，酸性溶液较为稳定。水中
  • Acros Organics:L(+)-半胱氨酸/L(+)-巯基氨基丙酸 L-Cysteine, 99+%(52-90-4)
  • 用途二:用于医药、食品、化妆品等
  • {AL

系列性分类

  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Amino Acids 氨基酸
  1. Application Areas 应用领域分类
  2. Flavors and Fragrances 香精香料
  3. Alphabetical Listings - Flavors and Fragrances
  4. C-D - Alphabetical Listings
  1. Life Science 生命科学
  2. Metabolomics 代谢组学
  3. Metabolic Libraries - Metabolomics
  4. Amino Acid Library - Metabolic Libraries
  1. Life Science 生命科学
  2. Nutrition Research 营养研究
  3. Functional Foods - Nutrition Research
  4. Amino acids - Functional Foods
  1. Life Science 生命科学
  2. Nutrition Research 营养研究
  3. Phytochemicals by Plant (Food/Spice/Herb) - Nutrition Research
  4. Allium sativum (Garlic) - Phytochemicals by Plant (Food/Spice/Herb)
  1. Life Science 生命科学
  2. Nutrition Research 营养研究
  3. Phytochemicals by Plant (Food/Spice/Herb) - Nutrition Research
  4. Hypericum perforatum (St John′s wort) - Phytochemicals by Plant (Food/Spice/Herb)
  1. C2 to C5 - Amines
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Chromatography - Analytical Standards
  4. Food & Beverage Standards - Chromatography
  5. E numbers (Food Additives) - Food & Beverage Standards
  6. E900–E999 (miscellaneous) - E numbers (Food Additives)
  1. Chemical Synthesis 化学合成
  2. Chemical Biology 生物化学
  3. Peptide Chemistry 多肽化学
  4. Amino Acid Derivatives 氨基酸及其衍生物
  5. Cysteine/Cystine - Amino Acid Derivatives
  1. Life Science 生命科学
  2. Metabolomics 代谢组学
  3. Metabolic Pathways - Metabolomics
  4. Metabolites and Cofactors on the Metabolic Pathways Chart - Metabolic Pathways
  5. Cofactor - Metabolites and Cofactors on the Metabolic Pathways Chart
  6. Pantothenate - Cofactor
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. BioChemika Ultra
  4. Antioxidants
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Amino Acids and Vitamins
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Amino Acids
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Albumins and Transport Proteins
  4. Albumin
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Biochemicals Found in Plants
  4. Alkaloid
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Culture
  4. Amino Acids and Vitamins
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Metabolomics
  4. Metabolic Libraries
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Reagents and Supplements
  4. Amino Acids and Vitamins
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Enzymes, Inhibitors, and Substrates
  4. Metabolomics
  5. Metabolic Libraries
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Culture
  4. Reagents and Supplements
  5. Amino Acids and Vitamins
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Metabolomics
  4. Metabolic Pathways
  5. Metabolites and Cofactors on the Metabolic Pathways Chart
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Nutrition Research
  4. Biochemicals Found in Plants
  5. Alkaloid
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Enzymes, Inhibitors, and Substrates
  4. Metabolomics
  5. Metabolic Pathways
  6. Metabolites and Cofactors on the Metabolic Pathways Chart
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Metabolomics
  4. Metabolic Pathways
  5. Metabolites and Cofactors on the Metabolic Pathways Chart
  6. Cholesterol
  1. Medical Research Areas
  2. Metabolism
  3. Endogenous Metabolite  (内源性代谢物)

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