(2S)-pyrrolidine-2-carboxylic acid

• ChemBase编号: 57
• 分子式: C5H9NO2
• 平均质量: 115.13046
• 单一同位素质量: 115.06332853
• SMILES: OC(=O)[C@H]1NCCC1
• Canonical SMILES: OC(=O)[C@@H]1CCCN1
• InChI: InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1
• InChIKey: ONIBWKKTOPOVIA-BYPYZUCNSA-N

名称和登记号

名称

• IUPAC标准名: (2S)-pyrrolidine-2-carboxylic acid
• IUPAC传统名: L-proline
• 别名: (S)-吡咯烷-2-羧酸; L-脯氨酸; 2-Pyrrolidine carboxylic acid; L-(-)-proline; H-Pro-OH; 2-Pyrrolidinecarboxylic acid; (S)-Proline; (S)-2-Pyrrolidinecarboxylic acid; (S)-2-Carboxypyrrolidine; (-)-Proline; (-)-2-Pyrrolidinecarboxylic acid; L-Proline; L-PROLINE, U.S.P.; (S)-Pyrrolidine-2-carboxylic acid; L-Proline; Proline; 2-Pyrrolidinecarboxylic acid; L-Proline; (2S)-pyrrolidine-2-carboxylic acid

登记号

• CAS号: 147-85-3
• EC号: 205-702-2
• MDL号: MFCD00064318
• Beilstein号: 80810
• 默克索引号: 147780
• PubChem SID: 24901637; 24898677; 24887886; 24898986; 46506858; 160963520; 24898097; 24887885
• PubChem CID: 145742
• FEMA编号: 3318
• 欧洲委员会编号: 10378
• Flavis Number: 17.019

理论计算性质

JChem

• Acid pKa: 1.9406707
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): -2.5687168
• LogD (pH = 7.4): -2.5686643
• Log P: -2.5686383
• 摩尔折射率: 28.0643 cm^3
• 极化性: 11.294152 Å^3
• 极化表面积: 49.33 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -2.71
• LOG S: 0.5
• 溶解度: 3.65e+02 g/l

分子性质

理化性质

• 溶解度: H2O: soluble1 M at 20 °C, clear, colorless; H2O: soluble50 mg/mL; Soluble
• 外观: powder; Powder
• 熔点: 220-222°C; 228 °C (dec.)(lit.); ca 225°C dec.
• 密度: 1.36
• 比旋光度: [α]20/D -84.5±1°, c = 5% in H2O; [α]20/D -84°, c = 4 in H2O; [α]20/D -85.0±1.0°, c = 5% in H2O; -84 (c=1 in water)
• 紫外吸收波长: λ: 260 nm Amax: 0.05; λ: 280 nm Amax: 0.05
• 疏水性(logP): -2.4; -2.413
• pH值: 6.0-7.0 (20 °C, 1 M in H2O); 6.0-7.0 (25 °C, 1 M in H2O)

安全信息

• 保存条件: Room Temperature (15-30°C)
• 保存注意事项: Hygroscopic; IRRITANT
• RTECS编号: TW3584000
• 德国WGK号: 1
• TSCA收录: false; 是
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Regulation Compliance: FCC; FDA 21 CFR (172.320)

产品相关信息

• 纯度: ≥99%; >99% (TLC); ≥98.5%; ≥99%; ≥99% (TLC); ≥99.0%; ≥99.0% (NT); ≥99.5% (NT); 95%; 95+%; 97%; 98%; 99%
• 级别: certified reference material; EP; Halal; Kosher; NI; ReagentPlus®; SAJ special grade; TraceCERT®; USP
• 光学纯度: ee: 98% (GLC)
• 适用性: meets EP, USP testing specifications; suitable for cell culture; suitable for manufacturing use
• 燃烧残渣: <0.1%; ≤0.1%; ≤0.1% (as SO4)
• 杂质: <0.0005% Phosphorus (P); <0.1% Insoluble matter; ≤0.3% foreign amino acids; endotoxin, tested; insoluble matter, passes filter test; L-Hydroxyproline, free
• 痕量阳离子: Al: <0.0005%; Al: ≤5 mg/kg; As: ≤0.1 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: <0.0005%; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: <0.0005%; Cu: ≤5 mg/kg; Fe: <0.0005%; Fe: ≤5 mg/kg; K: <0.005%; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: <0.0005%; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: <0.005%; Na: ≤50 mg/kg; NH4+: <0.05%; NH4+: ≤20 mg/kg; Ni: ≤5 mg/kg; Pb: <0.001%; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: <0.0005%; Zn: ≤5 mg/kg
• 痕量阴离子: chloride (Cl-): <0.05%; chloride (Cl-): ≤100 mg/kg; sulfate (SO42-): <0.05%; sulfate (SO42-): ≤100 mg/kg
• 生物来源: from non-animal source
• 干燥失重: ≤0.1% loss on drying, 20 °C (HV); ≤0.2% loss on drying, 110 °C
• 产品质量级别: GMP-COMPENDIA
• λ: 1 M in H2O
• 产品线: BioUltra; BioXtra
• abs.: A1M/260, H2O <0.05; A1M/280, H2O <0.05
• Empirical Formula (Hill Notation): C5H9NO2

详细说明

MP Biomedicals - 05217149

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02194728

Cell Culture Reagent
Crystalline
Purity: 99+%
Hydroxy-_L -proline free

MP Biomedicals - 02199543

Solid

MP Biomedicals - 02102730

Crystalline
Purity: 99+%
Hydroxy-L-proline free

DrugBank - DB00172

• Drug Groups: approved; nutraceutical
• Description: A non-essential amino acid that is synthesized from glutamic acid. It is an essential component of collagen and is important for proper functioning of joints and tendons. [PubChem]
• Indication: L-Proline is extremely important for the proper functioning of joints and tendons and also helps maintain and strengthen heart muscles.
• Pharmacology: L-Proline is a major amino acid found in cartilage and is important for maintaining youthful skin as well as repair of muscle, connective tissue and skin damage. It is also essential for the immune system, and for necessary balance of this formula. It is an essential component of collagen and is important for proper functioning of joints and tendons. L-Proline is extremely important for the proper functioning of joints and tendons. Helps maintain and strengthen heart muscles.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• External Links: Wikipedia

Sigma Aldrich - 81710

Other Notes
脯氨酸催化的不对称 Robinson 环化1;β-紫罗兰叉乙醛、视黄醛和相关化合物的不对称自缩合反应2

Sigma Aldrich - P8865

包装
按照 cGMP 制造和包装

Sigma Aldrich - 81709

Other Notes
Protects enzymes against heat inactivation1; Growth requirement of various microorganisms2

Sigma Aldrich - 131547

Application
酮不对称还原的催化剂。1用于氨基酸薄层色谱法分离的配体。2dolaproine 和相关非对映异构体的合成单体。3

Sigma Aldrich - W331902

包装
1 kg in poly bottle
1 sample in glass bottle
100 g in poly bottle
5 kg in fiber drum

Sigma Aldrich - 93693

Analysis Note
该有证标准物质 (CRM) 根据 ISO/IEC 17025 和 ISO 指南 34 生产和认证。该有证标准物质可溯源到 NIST 标准参考物质。
General description
证书上给出了含不确定度的认证含量（定量 NMR 法测定）和有效期。 证书下载：http://www.sigma-aldrich.com。
法律信息
TraceCERT 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - P0380

包装
1 kg in poly bottle
10 mg in autosmp vl
100 g in poly bottle
5 kg in poly drum
法律信息
ReagentPlus 注册商标 Sigma-Aldrich Co. LLC

参考文献

• For use as a catalyst in an asymmetric aldol cyclization, see: Org. Synth. Coll., 7, 363 (1990). For reaction scheme, see 2-Methylcyclopentane-1,3-dione, A13936. For use in a direct enantioselective crossed aldol reaction with aldehydes, see: J. Am. Chem. Soc., 124, 6798 (2002). For use as an organoctalyst in direct aldol reactions of ɑ-oxyaldehydes, as the first step in a two-step synthesis of carbohydrates, see: Angew. Chem. Int. Ed., 43, 2152 (2004). Mediates the enantioselective borane reduction of ketones to chiral alcohols with moderate to good ee: Monatsh. Chem., 131, 91 (2000). Also used to induce high ee in the ɑ-amination of aldehydes with Dibenzyl azodicarboxylate, L19347: J. Am. Chem. Soc., 124, 5656 (2002), or Diethyl azodicarboxylate, L19348: Angew. Chem. Int. Ed., 41, 1790 (2002).
• For a review of the use of proline as a chiral catalyst, see: Synlett, 1675 (2001); Synlett, 1973 (2006).
• For preparation from L-proline of the chiral hydrazone "SAMP", and enantioselective syntheses using the RAMP/ SAMP methodology, see: Org. Synth. Coll., 8, 26, 403 (1985).
• For formation of a fused pyrrolidino-oxazolidinone, and use of the product in a synthesis of enantiopure ɑ-branched amino acids, see: Org. Synth. Coll., 9, 626 (1998); for reaction scheme, see Trimethylacetaldehyde, A15013.
• The Li salt has been used as a catalyst for the Michael addition of dimethyl malonate to ɑ?-unsaturated aldehydes: J. Chem. Soc., Chem. Commun., 1088 (1991).