3-(3,4-Dihydroxyphenyl)-L-alanine 3.4-二羟基-L-苯丙氨酸

CAS 59-92-7 MFCD00002598

化学结构图

59-92-7
SMILES: N[C@@H](Cc1ccc(O)c(O)c1)C(=O)O

化学属性

Mol. FormulaC9H11NO4
Mol. Weight197
Density1.468
Melting Point276-278
TSCAYes
Appearance 白色或类白色结晶性粉末。熔点285.5℃（分解）。易溶于稀酸，微溶于水，不溶于乙醇、乙醚枵氯仿。无臭，无味，在空气中变黑。
Refractive index-12 ° (C=5, 1mol/L HCl)
SolubilitySoluble in water (66 mg/ml), DMSO (<1 mg/ml at 25 °C), and 0.5M HCl (50 mg/ml). Insoluble in ethanol, and chloroform.
Stability对光和空气敏感

别名和识别编码

Chemical Name3-(3,4-Dihydroxyphenyl)-L-alanine
Synonym (-)-(3,4-Dihydroxyphenyl)alanine (-)-3,4-Dihydroxyphenylalanine (-)-3-(3,4-Dihydroxyphenyl)-L-alanine (-)-Dopa 3,4-DIHYDROXY-L-PHE 3,4-Dihydroxyphenylalanine(f 3-(3,4-二羟基苯基)-L-丙氨酸 3-羟基-L-酪氨酸 左旋多巴 L-DOPA 左多巴 3-(3,4-二羟基苯基)-L-丙氨酸 3-羟基-L-酪氨酸 L-DOPA 左多巴 3-Hydroxy-L-tyrosine DOPA Deadopa Dopaston SE H L-(3,4-Dihydroxyphenyl)alanine L-3-(3,4-二羟苯基)苯胺 L-3-(3,4-二羟苯基）丙氨酸 L-3-(3,5-二羟苯基)苯胺 L-B-(3,4-二羟基苯)丙氨酸 L-DOPA, 3-(3,4-Dihydroxyphenyl)-L-alanine L-β-3,4-dihydroxyphenyl-alanine Larodopa Levopa Veldopa {} {} {} {} {hazard_co 左多巴 左旋多巴,3-羟基-L-酪氨酸
MDL NumberMFCD00002598
CAS Number59-92-7
EC Number200-445-2
Beilstein Registry Number2215169
PubChem Substance ID87567249
Reaxys-RN2215169
Merck Number5464
Chemical Name Translation3.4-二羟基-L-苯丙氨酸
Wiswesser Line NotationQVYZ1R CQ DQ -L
LabNetwork Molecule IDLN00235827
InChIInChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1
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分类

  • {SNA} Analytical S
  • {SNA} Analytical Standards, EP Standards, EP Standards L - M, Pharmacopeia & Metrological Institutes Standards, 分析/色谱
  • {SNA} Bioactive Small Molecules, Catecholamine, Cell Signaling and Neuroscience,
  • {SNA} Analytical Standards,
  • {SNA} Analytical Standards, Analytical/Chromatography, Chromatography, EP Standards, EP Standards L - M, Pharmaceutical Standards, Pharmacopeia Standards
  • {SNA} Catecholamine,
  • {SNA} Bioactive Small Molecules,
  • {SNA} Bioactive Small Molecules, Catecholamine,
  • {SNA} Additional Standards, Analytical Standards, Chromatography, Pharmaceutical Secondary Standards, Pharmaceutical Standards, Pharmacopeia & Metrological Institutes Standards, Secondary Standards, 分析/色谱
  • {SNA} Analytical

产品应用

  • An immediate precursor of dopamine and product of tyrosine hydroxylase.

相关文献及参考

  • [2]. Merims D, et al. Dopamine dysregulation syndrome, addiction and behavioral changes in Parkinson's disease. Parkinsonism Relat Disord. 2008;14(4):273-80. Epub 2007 Nov 7.
  • [3]. Perez-Pardo P, et al. Additive Effects of Levodopa and a Neurorestorative Diet in a Mouse Model of Parkinson's Disease. Front Aging Neurosci. 2018 Aug 3;10:237.
  • [4]. Park HJ, et al. Anti-allodynic effects of levodopa in neuropathic rats. Yonsei Med J. 2013 Mar 1;54(2):330-5.
  • Feigin, A., Metabolic correlates of levodopa response in Parkinson's disease. Neurology 57 , 2083, (2001) 摘要
  • Merck 14 ,5464
  • Merck:14,5464
  • Merck:14,5464 Beilstein:14(1)681
  • Short: EINECS
  • Short: III/10a
  • Tabar, et al., The effects on central dopamine function of chronic L-DOPA (methyl ester hydrochloride) treatment of mice. Pharmacol. Biochem. Behav. 33 , 139, (1989) 摘要
  • [1]. Hyland K, et al. Aromatic L-amino acid decarboxylase deficienc

安全信息

Signal word Warning
GHS Symbol
WGK Germany3
Safety Statements
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触；
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
  • S36 Wear suitable protective clothing 穿戴适当的防护服；
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
Precautionary statements
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • 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。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P301+P312+P330
  • P302+P352+P332+P313+P362+P364
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • P332+P313
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服，清洗后方可重新使用
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
RTECSAY5600000
Hazard statements
  • H315 Causes skin irritation 会刺激皮肤
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H302 Harmful if swallowed 吞食有害
  • H319 Causes serious eye irritation 严重刺激眼睛
Hazard Codes Xn
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
Storage condition 充氩保存 2-8°C 
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - man
DOSE/DURATION           : 87520 mg/kg/1.5Y-C
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Skin and Appendages - tumors
REFERENCE :
   NEURAI Neurology.  (Modern Medicine Pub., Inc., 1 E. First St., Duluth, MN
   55802)  V.1-    1951-  Volume(issue)/page/year: 24,340,1974

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 2363 mg/kg
TOXIC EFFECTS :
   Behavioral - excitement
REFERENCE :
   TXAPA9 Toxicology and Applied Pharmacology.  (Academic Press, Inc., 1 E.
   First St., Duluth, MN 55802) V.1-    1959-  Volume(issue)/page/year:
   28,1,1974

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 4449 mg/kg
TOXIC EFFECTS :
   Peripheral Nerve and Sensation - local anesthetic
   Behavioral - convulsions or effect on seizure threshold
   Gastrointestinal - changes in structure or function of salivary glands
REFERENCE :
   IYKEDH Iyakuhin Kenkyu.  Study of Medical Supplies.  (Nippon Koteisho
   Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan)  V.1- 1970- 
   Volume(issue)/page/year: 3,186,1972

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Bird - wild bird species
DOSE/DURATION           : 100 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   AECTCV Archives of Environmental Contamination and Toxicology.
   (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ
   070944)  V.1-    1973-  Volume(issue)/page/year: 12,355,1983

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : 609 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   TXAPA9 Toxicology and Applied Pharmacology.  (Academic Press, Inc., 1 E.
   First S

TYPE OF TEST            : DNA damage
TEST SYSTEM             : Human Cells - not otherwise specified
DOSE/DURATION           : 3 mmol/L
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   42,3783,1982

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Human Fibroblast
DOSE/DURATION           : 3 mmol/L
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   42,3783,1982

TYPE OF TEST            : Micronucleus test
TEST SYSTEM             : Rodent - hamster Lung
DOSE/DURATION           : 98500 ug/L
REFERENCE :
   SNSHBT Senshokutai.  Chromosome.  (Sensyokutai Gakkai, Kaokusai Kirisutokyo
   Daigaku, Mitaka, Tokyo-to, Japan)  No.1-    1946-    Adopted new numbering
   in 1976.  Volume(issue)/page/year: (20),574,1980

TYPE OF TEST            : DNA damage
TEST SYSTEM             : Rodent - rat Lung
DOSE/DURATION           : 25 umol/L
REFERENCE :
   ABCHA6 Agricultural and Biological Chemistry.  (Maruzen Co. Ltd., POB 5050,
   Tokyo International, Tokyo 100-31, Japan)  V.25-    1961-
   Volume(issue)/page/year: 39,795,1975

TYPE OF TEST            : Mutation in mammalian somatic cells
TEST SYSTEM             : Rodent - mouse Lymphocyte
DOSE/DURATION           : 100 mg/L
REFERENCE :
   EMMUEG Environmental and Molecular Mutagenesis.  (Alan R. Liss, Inc., 41

TYPE OF TEST            : Micronucleus test
TEST SYSTEM             : Human Embryo
DOSE/DURATION           : 39400 ug/L
REFERENCE :
   SNSHBT Senshokutai.  Chromosome.  (Sensyokutai Gakkai, Kaokusai Kirisutokyo
   Daigaku, Mitaka, Tokyo-to, Japan)  No.1-    1946-    Adopted new numbering
   in 1976.  Volume(issue)/page/year: (20),574,1980

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 5 gm/kg
SEX/DURATION            : female 6-15 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Fertility - other measures of fertility
REFERENCE :
   AUCMBJ Acta Universitatis Carolinae, Medica, Monographia.  (Univerzita
   Karlova, Ovocny Trh. 3, 11636 Prague 1, Czechoslovakia)  No.1-    1954-
   Volume(issue)/page/year: 61,251,1973

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 500 mg/kg
SEX/DURATION            : female 1-5 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - other developmental
   abnormalities
REFERENCE :
   TXAPA9 Toxicology and Applied Pharmacology.  (Academic Press, Inc., 1 E.
   First St., Duluth, MN 55802) V.1-    1959-  Volume(issue)/page/year:
   38,251,1976

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 6600 mg/kg
SEX/DURATION            : female 7-17 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
   Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight
   gain)
REFERENCE :
   YACHDS Yakuri to Chiryo.  Pharmacology and Therapeutics.  (Raifu Saiensu
   Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan)  V.1-    1972-
   Volume(issue)/page/year: 15(Suppl 2),283,1987

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rabbit
DOSE                    : 2250 mg/kg
SEX/DURATION            : female 7-15 day(s) after conception
TOXIC EFFECTS :
   Reproductiv

其他信息

  • Sigma Aldrich:59-92-7(sigmaaldrich)
  • 系非蛋白氨基酸。L构型，自水中得无色针状结晶。易溶于稀盐酸与甲酸，溶于水，不溶于乙醇、苯、氯仿与乙酸乙酯。在动物体内，多巴经多巴脱羧酶的作用转化为多巴胺。
  • 上游原料:均三甲苯 --> L-酪氨酸 --> 强酸性苯乙烯系阳离子交换树脂 --> 黑色素 --> 多巴
  • Acros Organics:L-多巴/3-(3,4-二羟基苯基)-L-丙氨酸 L-3-(3,4-Dihydroxyphenyl)alanine, 99%(59-92-7)
  • MOL 文件:59-92-7.mol
  • Alfa Aesar:L-3-(3,5-二羟苯基)苯胺,99% 3,4-Dihydroxy-L-phenylalanine, 98+%(59-92-7)
  • 存储注意事项:空气敏感;光敏感
  • 图谱信息:左旋多巴(59-92-7)质谱(MS) 左旋多巴(59-92-7)红外图谱(IR2) 左旋多巴(59-92-7)红外图谱(IR1) 左旋多巴(59-92-7)Raman光谱
  • MSDS 信息:Levodopa(59-92-7).msds
  • F:10-23
  • 用途二:多巴与多巴胺为重要的神经介质。为酪氨酸酶(tyrosinase)、芳香族L-氨基酸脱羧酶（decarboxylase）和乳过氧化物酶(lactoperoxidase)的底物。
  • 用途一:左旋多巴是目前治疗震颤麻痹的有效药物之一，为体内合成去甲肾上腺素、多巴胺等的前体之一，属儿茶酚胺。左旋多巴能通过血脑屏障进入脑中，经多马脱羧酶脱羧转化成多巴胺而发挥作用。但显效较慢，副作用较大。大鼠口服LD50>4000mg/kg。
  • 比旋光度:-11.7 ° (c=5.3, 1N HCl)
  • 方法一:多巴含于一些豆科植物中，在氧化酶作用下能氧化聚合，生成黑素（melanin）。一些豆科植物的荚在成熟时变黑。人及动物的毛、乌贼的墨法、西瓜的种皮等黑色素也属于这类黑素。从藜（Mucuna sempervirens Hemsl）种子中可提取出氨基酸类——左旋多巴。提取方法如下：将藜豆粉碎，用30%乙醇与0.1%乙酸的混合液常温提取3次，每次24h。过滤，得提取液。将提取液减压（21.3kPa）浓缩，析出结晶，在0-10℃静置过夜，过滤，和左旋多巴粗品。粗品用1N盐酸溶解，加活性炭过滤，滤液加少量维生素C用2N氨水中和至pH3.5，析出大量结晶。0-10℃静置4h，过滤。滤饼用含少量维生素C的蒸馏水洗2次，丙酮淋洗脱水1次。60-70℃干燥得左旋多巴。以豆粉计，收率约为2%。左旋多巴也可由L-酪氨酸氧化得到。将酪氨酸溶于甲酸磷酸中，升温至40℃保温12h，用20倍的蒸馏水稀释。稀释液通过强酸性苯乙烯系阳离子交换树脂吸附未反应的酪氨酸，再经后片理操作即得成品。
  • 检测方法:HPLC,NMR
  • TCI Shanghai:3-(3,4-二羟基苯基)-L-丙氨酸 3-(3,4-Dihydroxyphenyl)-L-alanine,>;98.0%(LC)(T)(59-92-7)
  • Levodopa is a natural form of DOPA used in the treatment of Parkinson's disease. Immediate precursor of dopamine and product of tyrosine hydroxylase.
  • 左旋多巴价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 D0600 3-(3,4-二羟基苯基)-L-丙氨酸 3-(3,4-Dihydroxyphenyl)-L-alanine 25G 1030元 2014/06/02 D0600 3-(3,4-二羟基苯基)-L-丙氨酸 3-(3,4-Dihydroxyphenyl)-L-alanine 5G 375元 2010/06/21 167530050 左旋多巴 L-3-(3,4-Dihydroxyphenyl)alanine 99% 5 GR 459元
  • 下游产品:

系列性分类

  1. Life Science 生命科学
  2. Nutrition Research 营养研究
  3. Phytochemicals by Chemical Classification - Nutrition Research
  4. Plant Extracts - Phytochemicals by Chemical Classification
  1. Chemical Synthesis 化学合成
  2. Chemical Biology 生物化学
  3. Peptide Chemistry 多肽化学
  4. Unnatural Amino Acid Derivatives 人工合成氨基酸
  5. Phenylalanine Derivatives - Unnatural 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. Catecholamine - Cofactor
  1. Functional Group 官能团索引
  2. 1,2-diphenol
  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. GPCR & G Protein
  3. Dopamine Receptor  (多巴胺受体)
  1. Medical Research Areas
  2. Metabolism
  3. Endogenous Metabolite  (内源性代谢物)