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147028-80-6 分子结构
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(2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid

ChemBase编号:91182
分子式:C5H9NO3
平均质量:131.12986
单一同位素质量:131.05824315
SMILES和InChIs

SMILES:
N1C[C@@H](C[C@H]1C(=O)O)O
Canonical SMILES:
O[C@H]1CN[C@@H](C1)C(=O)O
InChI:
InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m1/s1
InChIKey:
PMMYEEVYMWASQN-DMTCNVIQSA-N

引用这个纪录

CBID:91182 http://www.chembase.cn/molecule-91182.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid
IUPAC传统名
hydroxyproline
hypro
别名
(2S,4R)-4-羟基吡咯烷-2-羧酸
L-羟基脯氨酸
反-4-羟基-L-脯氨酸
trans-4-Hydroxy-L-proline
(2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acid
(2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acid
L-HYDROXYPROLINE
Hyp
trans-4-Hydroxy-L-proline
cis-4-Hydroxy-D-proline
D-4-allo-Hydroxy-proline
(2R,4R)-4-Hydroxypyrrolidine-2-carboxylic Acid
(4R)-4-Hydroxy-D-proline
(R)-allo-Hydroxyproline
4-(R)-Hydroxypyrrolidine-2-(R)-carboxylic Acid
4-Hydroxy-D-alloproline
4-allo-Hydroxy-D-proline
D-allo-4-Hydroxyproline
D-allo-Hydroxyproline
D-cis-4-Hydroxyproline
NSC 524341
cis-4-Hydroxy-D-proline
(-)-4-Hydroxy-2-pyrrolidinecarboxylic Acid
(2S,4R)-(-)-4-Hydroxyproline
(R)-4-Hydroxy-(S)-proline
4(R)-Hydroxy-2(S)-pyrrolidinecarboxylic Acid
4-trans-Hydroxy-L-proline
L-Hypro
NSC 46704
trans-4-Hydroxy-L-proline
trans-4-Hydroxy-D-proline
(2S,4R)-(-)-4-Hydroxypyrrolidine-2-carboxylic acid
H-Hyp-OH
4-Hydroxyproline
Hydroxyproline
CAS号
147028-80-6
51-35-4
2584-71-6
3398-22-9
EC号
200-091-9
MDL号
MFCD00064320
Beilstein号
81441
471933
默克索引号
144840
PubChem SID
24895692
24895700
24880041
162077886
PubChem CID
5810

理论计算性质

理论计算性质

JChem
Acid pKa 1.641382  质子受体
质子供体 LogD (pH = 5.5) -3.7163465 
LogD (pH = 7.4) -3.7165344  Log P -3.7163188 
摩尔折射率 29.3822 cm3 极化性 11.9828205 Å3
极化表面积 69.56 Å2 可自由旋转的化学键
里宾斯基五规则 true 

分子性质

分子性质

理化性质 安全信息 产品相关信息 生物活性(PubChem)
溶解度
H2O: soluble50 mg/mL expand 查看数据来源
Water expand 查看数据来源
外观
White Solid expand 查看数据来源
熔点
270-273°C dec. expand 查看数据来源
273 °C (dec.)(lit.) expand 查看数据来源
273(dec.)°C expand 查看数据来源
285-287°C (dec.) expand 查看数据来源
比旋光度
[α]20/D -76.0±1.5°, c = 5% in H2O expand 查看数据来源
[α]25/D -75.6°, c = 1 in H2O expand 查看数据来源
-76 (c=4 in water) expand 查看数据来源
保存条件
Refrigerator, Under Inert Atmosphere expand 查看数据来源
保存注意事项
Irritant expand 查看数据来源
RTECS编号
TW3586500 expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
TSCA收录
expand 查看数据来源
个人保护装置
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand 查看数据来源
纯度
≥98.5% expand 查看数据来源
≥99% expand 查看数据来源
≥99.0% (NT) expand 查看数据来源
97% expand 查看数据来源
98% expand 查看数据来源
99+% expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
适用性
cell culture tested expand 查看数据来源
suitable for cell culture expand 查看数据来源
燃烧残渣
≤0.1% (as SO4) expand 查看数据来源
杂质
≤0.3% foreign amino acids expand 查看数据来源
endotoxin, tested expand 查看数据来源
痕量阳离子
Ca: ≤10 mg/kg expand 查看数据来源
Cd: ≤5 mg/kg expand 查看数据来源
Co: ≤5 mg/kg expand 查看数据来源
Cr: ≤5 mg/kg expand 查看数据来源
Cu: ≤5 mg/kg expand 查看数据来源
Fe: ≤5 mg/kg expand 查看数据来源
K: ≤50 mg/kg expand 查看数据来源
Mg: ≤5 mg/kg expand 查看数据来源
Mn: ≤5 mg/kg expand 查看数据来源
Na: ≤50 mg/kg expand 查看数据来源
NH4+: ≤100 mg/kg expand 查看数据来源
Ni: ≤5 mg/kg expand 查看数据来源
Pb: ≤5 mg/kg expand 查看数据来源
Zn: ≤5 mg/kg expand 查看数据来源
痕量阴离子
chloride (Cl-): ≤100 mg/kg expand 查看数据来源
sulfate (SO42-): ≤100 mg/kg expand 查看数据来源
生物来源
microbial expand 查看数据来源
干燥失重
≤0.1% loss on drying, 110 °C expand 查看数据来源
产品线
BioXtra expand 查看数据来源
Empirical Formula (Hill Notation)
C5H9NO3 expand 查看数据来源

详细说明

详细说明

MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals -  05203349 external link
MP Biomedicals Rare Chemical collection
Sigma Aldrich -  H5534 external link
Other Notes
动物结构蛋白(如胶原和弹性蛋白)的天然成分。
包装
10 mg in autosmp vl
Biochem/physiol Actions
Hydroxyproline (4-hydroxyproline) is a non-proteinogenic amino acid formed by the post-translational hydroxylation of proline. Hydroxyproline is a major component of collagen, where it serves to stabilize the helical structure. Because hydroxyproline is largely restricted to collagen, the measurement of hydroxylproline levels can be used as an indicator of collagen content. Conditions that increase collagen turnover can elevate serum and urine hydroxyproline levels. Urine and serum hydroxyproline levels can be used as a marker for bone resorption.
Sigma Aldrich -  H3656 external link
Other Notes
动物结构蛋白(如胶原和弹性蛋白)的天然成分。
Sigma Aldrich -  56250 external link
Other Notes
动物结构蛋白(如胶原和弹性蛋白)的天然成分。
Enzymes and intermediates of hydroxyproline degradation1
Biochem/physiol Actions
Trans-4-Hydroxy-L-proline is used as a starting material in the synthesis of (-)-secrinine; the synthesis of prolinol-based nucleotide analogues with N-phosphonomethyl moiety attached to the nitrogen atom of prolinol ring and in asymmetric synthesis of the ABC-ring system of the antitumor antibiotic MPC1001.
Trans-4-Hydroxy-L-proline is used in the organic synthesis of depsilairdin analogues, noncompetitive peptidomimetic inhibitors of multidrug resistance P-glycoprotein and 3-guaninyl-5-hydroxymethyl-2-pyrrolidinone (4) or 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone (5) nucleoside analogues.
Sigma Aldrich -  H54409 external link
Other Notes
动物结构蛋白(如胶原和弹性蛋白)的天然成分。
包装
10, 25, 100 g in poly bottle
2.5 g in glass bottle
Application
合成神经兴奋 kainoid 1和抗真菌棘白菌素的多功能试剂。2也可用于合成手性配体,该配体可用于醛的不对称乙基化。3
Toronto Research Chemicals -  H952376 external link
A natural constituent of animal structural proteins such as collagen and elastin. Several microorganisms producing proline trans-4- and cis-3-hydroxylase were discovered and these enzymes were applied to the industrial production of trans-4- and cis-3-hyd

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Langmaier, F. et al.: Int. J. Cosm. Sci., 24, 273 (2002)
  • Lawrence, C., et al.: Biochem. J., 313, 185 (2002)
  • Mori, H., et al.: J. Bacteriol.; 179, 5677 (2002)
  • Clifton, I., et al.: Eur. J. Biochem., 268, 6625 (2002)
  • Chiral precursor for a wide variety of synthetic targets. For discussion of some examples, see: Tetrahedron, 52, 13803 (1996).
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专利

专利

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