(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid

• ChemBase编号: 36
• 分子式: C11H12N2O2
• 平均质量: 204.22518
• 单一同位素质量: 204.08987763
• SMILES: OC(=O)[C@@H](N)Cc1c2c([nH]c1)cccc2
• Canonical SMILES: OC(=O)[C@H](Cc1c[nH]c2c1cccc2)N
• InChI: InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1
• InChIKey: QIVBCDIJIAJPQS-VIFPVBQESA-N

名称和登记号

名称

• IUPAC标准名: (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
• IUPAC传统名: L-tryptophan; L-tryptophan(.)
• 商标名: Alti-Tryptophan; Lyphan
• 别名: L-色胺酸; (S)-2-氨基-3-(3-吲哚基)丙酸; L-α-氨基-3-吲哚丙酸; L-色氨酸; D-2-Amino-3-indolepropionic acid; D-TRYPTOPHAN; L-2-Amino-3-indolepropionic acid; (S)-2-amino-3-(1H-indol-3-yl)propanoic acid; H-Trp-OH; (+/-)-Tryptophan; (-)-1H-Indole-3-alanine; NSC 13119; l-α-Aminoindole-3-propionic Acid; (-)-Tryptophan; L-(-)-Tryptophan; L-Tryptophane; Tryptophan; Tryptophane; alpha-Amino-beta-(3-indolyl)-propionic acid; l-a-Aminoindole-3-propionic acid; l-b-3-Indolylalanine; (S)-a-Amino-1H-indole-3-propanoic acid; (S)-a-Amino-b-indolepropionic acid; (S)-a-Aminoindole-3-propionic acid; (S)-Tryptophan; 2-Amino-3-indolylpropanoic acid; 3-Indol-3-ylalanine; L-Tryptophan; 2-Amino-3-(1H-indol-3-yl)propanoic acid; L-Tryptophan; 2-Amino-3-(1H-indol-3-yl)propanoic acid; Tryptophan; L-Trytophane; Indole-3-Alanine; alpha-Amino-3-Indoleproprionic Acid; L-TRYPTOPHAN, U.S.P.; (S)-2-Amino-3-(3-indolyl)propionic acid; L-α-Amino-3-indolepropionic acid

登记号

• CAS号: 73-22-3; 153-94-6
• EC号: 200-795-6; 205-819-9
• MDL号: MFCD00064340
• Beilstein号: 86197
• 默克索引号: 149797
• PubChem SID: 24900575; 24889916; 160963499; 24900200; 24278135; 46508329
• PubChem CID: 6305
• CHEBI ID: 27897
• ATC码: N06AX02
• CHEMBL: 54976
• Chemspider ID: 6066
• DrugBank ID: DB00150
• IUPHAR配体索引: 717
• KEGG ID: D00020
• 美国药典/FDA物质标识码: 8DUH1N11BX
• 维基百科标题: Tryptophan

理论计算性质

JChem

• Acid pKa: 2.5439286
• 质子受体: 3
• 质子供体: 3
• LogD (pH = 5.5): -1.0856168
• LogD (pH = 7.4): -1.0892947
• Log P: -1.085457
• 摩尔折射率: 56.2028 cm^3
• 极化性: 23.092001 Å^3
• 极化表面积: 79.11 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: -1.1
• LOG S: -2.18
• 溶解度: 1.36e+00 g/l

分子性质

理化性质

• 溶解度: 0.5 M HCl: soluble0.1 g/mL at 20 °C, clear, colorless to faintly yellow; 1 M HCl: soluble10 mg/mL; Soluble; Soluble in hot alcohol, alkali hydroxides; insoluble in chloroform.; Soluble: 0.23 g/L at 0 °C,; 11.4 g/L at 25 °C,; 17.1 g/L at 50 °C,; 27.95 g/L at 75 °C in water; Water
• 外观: powder; White Solid
• 熔点: >246°C (dec.); 280°C 285°C; 280-285 °C (dec.)(lit.); 289°C
• 比旋光度: [α]20/D -31.5±1°, c = 1% in H2O; [α]20/D -31.5°, c = 1 in H2O; -31 (c=1 in water)
• 疏水性(logP): -1.3
• pKa: 2.38 (carboxyl), 9.39 (amino)

安全信息

• 保存条件: Refrigerator; Room Temperature (15-30°C); Room Temperature (15-30°C), Protect from light
• RTECS编号: YN6129000; YN6130000
• 德国WGK号: 1
• TSCA收录: 是
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 相关基因信息: human ... TDO2(6999), TPH1(7166), TPH2(121278)

产品相关信息

• 纯度: ≥99%; ≥98% (TLC); ≥98.5%; ≥99.5% (NT); 97%; 98%; 99%; 99.0-101.0%
• 级别: certified reference material; EP; JP; reagent grade; TraceCERT®; USP
• 光学纯度: ee: 99% (GLC)
• 适用性: meets EP, JP, USP testing specifications; suitable for cell culture; suitable for manufacturing use
• 燃烧残渣: ≤0.1%
• 杂质: 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; 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: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤50 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-): ≤50 mg/kg; sulfate (SO42-): ≤50 mg/kg
• 生物来源: from non-animal source
• 干燥失重: ≤0.1% loss on drying, 20 °C (HV)
• 产品质量级别: GMP-COMPENDIA
• 产品线: BioUltra
• abs.: absorption0.5M/326 nm, 0.5 M HCl cut-off
• Empirical Formula (Hill Notation): C11H12N2O2
• 分类: Genuine Natural Compounds

详细说明

MP Biomedicals - 02103151

Purity: 99+%
Crystalline

MP Biomedicals - 02103144

Crystalline
Purity: 99%

MP Biomedicals - 02199561

White powder

MP Biomedicals - 02194758

Cell Culture Reagent
Purity: 99+%
Crystalline

DrugBank - DB00150

• Drug Groups: approved; nutraceutical
• Description: An essential amino acid that is necessary for normal growth in infants and for nitrogen balance in adults. It is a precursor of indole alkaloids in plants. It is a precursor of serotonin (hence its use as an antidepressant and sleep aid). It can be a precursor to niacin, albeit inefficiently, in mammals. [PubChem]
• Indication: Tryptophan may be useful in increasing serotonin production, promoting healthy sleep, managing depression by enhancing mental and emotional well-being, managing pain tolerance, and managing weight.
• Pharmacology: Tryptophan is critical for the production of the body's proteins, enzymes and muscle tissue. It is also essential for the production of niacin, the synthesis of the neurotransmitter serotonin and melatonin. Tryptophan supplements can be used as natural relaxants to help relieve insomnia. Tryptophan can also reduce anxiety and depression and has been shown to reduce the intensity of migraine headaches. Other promising indications include the relief of chronic pain, reduction of impulsivity or mania and the treatment of obsessive or compulsive disorders. Tryptophan also appears to help the immune system and can reduce the risk of cardiac spasms. Tryptophan deficiencies may lead to coronary artery spasms. Tryptophan is used as an essential nutrient in infant formulas and intravenous feeding. Tryptophan is marketed as a prescription drug (Tryptan) for those who do not seem to respond well to conventional antidepressants. It may also be used to treat those afflicted with seasonal affective disorder (a winter-onset depression). Tryptopan serves as the precursor for the synthesis of serotonin (5-hydroxytryptamine, 5-HT) and melatonin (N-acetyl-5-methoxytryptamine).
• Toxicity: Oral rat LD₅₀: > 16 gm/kg. Investigated as a tumorigen, mutagen, reproductive effector. Symptoms of overdose include agitation, confusion, diarrhea, fever, overactive reflexes, poor coordination, restlessness, shivering, sweating, talking or acting with excitement you cannot control, trembling or shaking, twitching, and vomiting.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.

Sigma Aldrich - T4196

Other Notes
血清素和褪黑激素的氨基酸前体
包装
按照 cGMP 要求进行制造和包装

Sigma Aldrich - T8941

Other Notes
血清素和褪黑激素的氨基酸前体
包装
10 mg in autosmp vl

Sigma Aldrich - 93659

Other Notes
血清素和褪黑激素的氨基酸前体
In tryptophan-substituted Sephadex® and Sepharose® for the improved chromatographic separation of cellulases1; As spacer in isotachophoresis of serum proteins2; Growth requirement of various microorganisms3.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 93659.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
法律信息
Sephadex is a registered trademark of GE Healthcare
Sepharose is a registered trademark of GE Healthcare

Sigma Aldrich - T90204

Other Notes
血清素和褪黑激素的氨基酸前体
Application
用于合成桥联吲哚生物碱。1

Sigma Aldrich - 51145

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
血清素和褪黑激素的氨基酸前体
法律信息
TraceCERT 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - T0254

Other Notes
血清素和褪黑激素的氨基酸前体
包装
1 kg in poly bottle
1, 5, 25, 100, 500 g in poly bottle

Toronto Research Chemicals - T947210

Essential amino acid.

参考文献

• Goze, C., et al.: Eur. J. Pharmacol., 643, 153 (2010)
• Bhandare, P., et al.: J. Chem. Pharm. Res., 2, 372 (2010)