(2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid

• ChemBase编号: 21
• 分子式: C9H11NO3
• 平均质量: 181.18854
• 单一同位素质量: 181.07389322
• SMILES: OC(=O)[C@@H](N)Cc1ccc(O)cc1
• Canonical SMILES: OC(=O)[C@H](Cc1ccc(cc1)O)N
• InChI: InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1
• InChIKey: OUYCCCASQSFEME-QMMMGPOBSA-N

名称和登记号

名称

• IUPAC标准名: (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid
• IUPAC传统名: L-tyrosine
• 商标名: Rxosine; Tyrosine; Tyrosine Power
• 别名: (S)-2-氨基-3-对羟苯基丙酸; 3-(4-对羟苯基)-L-丙氨酸; L-酪氨酸; H-Tyr-OH; 2-Amino-3-(p-hydroxyphenyl)propionic acid; 3-(p-Hydroxyphenyl)alanine; Free-Form L-Tyrosine; L-Tyrosine; β-p-Hydroxyphenylalanine; L-2-Amino-3-(4-hydroxyphenyl)propionic acid; 3-(4-Hydroxyphenyl)-L-alanine; 2-AMINO-3-HYDROXYBUTYRIC ACID; L-TYROSINE, U.S.P.; POLY-L-TYROSINE; L-2-Amino-3-(4-hydroxyphenyl)propanoic acid; Tyrosine; (S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (S)-2-Amino-3-(4-hydroxyphenyl)propionic acid; L-Tyrosine

登记号

• CAS号: 60-18-4; 556-03-6
• EC号: 200-460-4
• MDL号: MFCD00002606
• Beilstein号: 392441
• 默克索引号: 149839
• PubChem SID: 24900543; 24889931; 160963484; 24900206; 24901863; 24900164; 46507885
• PubChem CID: 1153; 6057
• CHEBI ID: 58315
• CHEMBL: 925
• Chemspider ID: 5833
• DrugBank ID: DB03839
• FEMA编号: 3736
• 维基百科标题: Tyrosine
• Flavis Number: 17.022

理论计算性质

JChem

• Acid pKa: 1.9998473
• 质子受体: 4
• 质子供体: 3
• LogD (pH = 5.5): -1.4884841
• LogD (pH = 7.4): -1.495157
• Log P: -1.488594
• 摩尔折射率: 47.0972 cm^3
• 极化性: 18.512522 Å^3
• 极化表面积: 83.55 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -2.39
• LOG S: -1.37
• 溶解度: 7.67e+00 g/l

分子性质

理化性质

• 溶解度: 1 M HCl: soluble0.5 M, clear, colorless (hot); 1 M HCl: soluble25 mg/mL; Slightly soluble
• 外观: powder
• 熔点: >300 °C (dec.)(lit.); >300°C; 255-257°C; 342-344°C
• 密度: 1.4 g/ml; 1.46
• 比旋光度: [α]20/D -10.6°, c = 4 in 1 M HCl; [α]20/D -11.5±1.0°, c = 4% in 1 M HCl; -11 (c=4 in 1N HCl)
• 疏水性(logP): -1.8

安全信息

• 保存条件: Room Temperature (15-30°C)
• RTECS编号: YP2275600
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 1
• 危险公开号: 36/37/38
• 安全公开号: 26; 26-37
• TSCA收录: 是
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: room temp

产品相关信息

• 纯度: ≥97%; ≥98% (HPLC); ≥99%; ≥99.0%; ≥99.0% (NT); 97%; 98%; 99%
• 级别: certified reference material; EP; NI; reagent grade; SAJ special grade; TraceCERT®; USP
• 光学纯度: ee: 98% (GLC)
• 包装: pkg of 1 g
• 适用性: meets EP, USP testing specifications; suitable for cell culture; suitable for manufacturing use
• 燃烧残渣: ≤0.1%; ≤0.1% (as SO4)
• 杂质: ≤0.5% foreign amino acids; endotoxin, tested; insoluble matter, passes filter test
• 痕量阳离子: Al: ≤5 mg/kg; As: ≤0.1 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: ≤10 mg/kg; Ca: ≤100 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: ≤100 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤200 mg/kg; NH4+: ≤200 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: ≤5 mg/kg
• 痕量阴离子: chloride (Cl-): ≤250 mg/kg; chloride (Cl-): ≤400 mg/kg; sulfate (SO42-): ≤100 mg/kg; sulfate (SO42-): ≤300 mg/kg
• 生物来源: from non-animal source
• 有效期: (limited shelf life, expiry date on the label)
• 干燥失重: ≤0.2% loss on drying, 20 °C (HV); ≤0.5% loss on drying, 110 °C
• 产品质量级别: GMP-COMPENDIA
• 产品线: BioUltra
• abs.: absorption0.5M/310 nm, 1 M HCl cut-off
• Pharmacopeia Traceability: traceable to PhEur T2900000; traceable to USP 1705006
• 线性分子式: 4-(HO)C6H4CH2CH(NH2)CO2H
• 分类: Genuine Natural Compounds

详细说明

MP Biomedicals - 05218193

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02199541

Solid

MP Biomedicals - 02194759

Cell Culture Reagent
Free Base
Crystalline

MP Biomedicals - 02103183

Crystalline
Free Base

DrugBank - DB00135

• Drug Groups: approved; nutraceutical
• Description: A non-essential amino acid. In animals it is synthesized from phenylalanine. It is also the precursor of epinephrine; thyroid hormones; and melanin. [PubChem]
• Indication: Tyrosine is claimed to act as an effective antidepressant, however results are mixed. Tyrosine has also been claimed to reduce stress and combat narcolepsy and chronic fatigue, however these claims have been refuted by some studies.
• Pharmacology: Tyrosine is a nonessential amino acid synthesized in the body from phenylalanine. Tyrosine is critical for the production of the body's proteins, enzymes and muscle tissue. Tyrosine is a precursor to the neurotransmitters norepinephrine and dopamine. It can act as a mood elevator and an anti-depressant. It may improve memory and increase mental alertness. Tyrosine aids in the production of melanin and plays a critical role in the production of thyroxin (thyroid hormones). Tyrosine deficiencies are manifested by hypothyroidism, low blood pressure and low body temperature. Supplemental tyrosine has been used to reduce stress and combat narcolepsy and chronic fatigue.
• Toxicity: L-Tyrosine has very low toxicity. There have been very few reports of toxicity. LD₅₀ (oral, rat) > 5110 mg/kg.
• Affected Organisms: Humans and other mammals
• Biotransformation: In the liver, L-tyrosine is involved in a number of biochemical reactions, including protein synthesis and oxidative catabolic reactions. L-tyrosine that is not metabolized in the liver is distributed via the systemic circulation to the various tissues of the body.
• Absorption: L-tyrosine is absorbed from the small intestine by a sodium-dependent active transport process.
• References: Hoffhines AJ, Damoc E, Bridges KG, Leary JA, Moore KL: Detection and purification of tyrosine-sulfated proteins using a novel anti-sulfotyrosine monoclonal antibody. J Biol Chem. 2006 Dec 8;281(49):37877-87. Epub 2006 Oct 17. [Pubmed] ; Molnar GA, Wagner Z, Marko L, Ko Szegi T, Mohas M, Kocsis B, Matus Z, Wagner L, Tamasko M, Mazak I, Laczy B, Nagy J, Wittmann I: Urinary ortho-tyrosine excretion in diabetes mellitus and renal failure: evidence for hydroxyl radical production. Kidney Int. 2005 Nov;68(5):2281-7. [Pubmed] ; Molnar GA, Nemes V, Biro Z, Ludany A, Wagner Z, Wittmann I: Accumulation of the hydroxyl free radical markers meta-, ortho-tyrosine and DOPA in cataractous lenses is accompanied by a lower protein and phenylalanine content of the water-soluble phase. Free Radic Res. 2005 Dec;39(12):1359-66. [Pubmed]
• External Links: Wikipedia; PDRhealth

Sigma Aldrich - T8566

Other Notes
多巴胺和其他儿茶酚胺的氨基酸前体
包装
10 mg in autosmp vl

Sigma Aldrich - 93829

Other Notes
多巴胺和其他儿茶酚胺的氨基酸前体
Growth requirements of various microorganisms1

Sigma Aldrich - T4321

Other Notes
多巴胺和其他儿茶酚胺的氨基酸前体
包装
按照 cGMP 要求进行制造和包装

Sigma Aldrich - W373605

Other Notes
多巴胺和其他儿茶酚胺的氨基酸前体
包装
1 kg in poly bottle
1 sample in glass bottle
100 g in poly bottle
5 kg in fiber drum

Sigma Aldrich - T90409

Other Notes
多巴胺和其他儿茶酚胺的氨基酸前体

Sigma Aldrich - 91515

Analysis Note
此认证标准物质 (CRM) 的生产和认证都符合 ISO/IEC 17025 和 ISO Guide 34 的要求。此 CRM 可溯源到 NIST CRM。
General description
认证的含量经定量 NMR 确定，并且证书上标明不确定度和有效期。 证书下载：http://www.sigma-aldrich.com。
Other Notes
多巴胺和其他儿茶酚胺的氨基酸前体
法律信息
TraceCERT 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 93830

Other Notes
多巴胺和其他儿茶酚胺的氨基酸前体

Sigma Aldrich - PHR1097

General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Other Notes
多巴胺和其他儿茶酚胺的氨基酸前体
Values of analytes vary lot to lot.

Sigma Aldrich - T3754

Other Notes
多巴胺和其他儿茶酚胺的氨基酸前体
包装
1 kg in poly bottle
50, 100, 500 g in poly bottle

Sigma Aldrich - 30-5530

Other Notes
多巴胺和其他儿茶酚胺的氨基酸前体

参考文献

• Hoffhines AJ, Damoc E, Bridges KG, Leary JA, Moore KL: Detection and purification of tyrosine-sulfated proteins using a novel anti-sulfotyrosine monoclonal antibody. J Biol Chem. 2006 Dec 8;281(49):37877-87. Epub 2006 Oct 17. Pubmed
• Molnar GA, Wagner Z, Marko L, Ko Szegi T, Mohas M, Kocsis B, Matus Z, Wagner L, Tamasko M, Mazak I, Laczy B, Nagy J, Wittmann I: Urinary ortho-tyrosine excretion in diabetes mellitus and renal failure: evidence for hydroxyl radical production. Kidney Int. 2005 Nov;68(5):2281-7. Pubmed
• Molnar GA, Nemes V, Biro Z, Ludany A, Wagner Z, Wittmann I: Accumulation of the hydroxyl free radical markers meta-, ortho-tyrosine and DOPA in cataractous lenses is accompanied by a lower protein and phenylalanine content of the water-soluble phase. Free Radic Res. 2005 Dec;39(12):1359-66. Pubmed