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

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