3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid

• ChemBase编号: 130443
• 分子式: C33H36N4O6
• 平均质量: 584.66214
• 单一同位素质量: 584.26348489
• SMILES: Cc1c(c([nH]c1/C=C\1/C(=C(C(=O)N1)C=C)C)Cc1c(c(c([nH]1)/C=C\1/C(=C(C(=O)N1)C)C=C)C)CCC(=O)O)CCC(=O)O
• Canonical SMILES: C=CC1=C(C)/C(=C/c2[nH]c(c(c2C)CCC(=O)O)Cc2[nH]c(c(c2CCC(=O)O)C)/C=C/2\NC(=O)C(=C2C=C)C)/NC1=O
• InChI: InChI=1S/C33H36N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-14,34-35H,1-2,9-12,15H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)
• InChIKey: BPYKTIZUTYGOLE-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid; 3-(2-{[3-(2-carboxyethyl)-5-[(3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl}-5-[(4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl)propanoic acid; 3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid
• IUPAC传统名: bilirubin; 3-(2-{[3-(2-carboxyethyl)-5-[(3-ethenyl-4-methyl-5-oxo-1H-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl}-5-[(4-ethenyl-3-methyl-5-oxo-1H-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl)propanoic acid; 3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid
• 别名: 胆红素; Pheophytin; Bilirubin; Bilirubin

登记号

• CAS号: 635-65-4
• EC号: 211-239-7
• MDL号: MFCD00005499
• Beilstein号: 74376
• 默克索引号: 141218
• PubChem SID: 162224722; 24891751; 24848604
• PubChem CID: 5280352
• CHEBI ID: 16990
• CHEMBL: 501680
• Chemspider ID: 4444055
• 美国药典/FDA物质标识码: RFM9X3LJ49
• 维基百科标题: Bilirubin

理论计算性质

• Acid pKa: 4.0274906
• 质子受体: 6
• 质子供体: 6
• LogD (pH = 5.5): 0.72434396
• LogD (pH = 7.4): -2.7640595
• Log P: 3.1191065
• 摩尔折射率: 168.896 cm^3
• 极化性: 61.830246 Å^3
• 极化表面积: 164.38 Å^2
• 可自由旋转的化学键: 12
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: aqueous acid: soluble; aqueous base: soluble; benzene: soluble; chloroform: soluble
• 外观: orange-brown powder

安全信息

• RTECS编号: DU3038000
• 德国WGK号: 2
• TSCA收录: 是
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

产品相关信息

• 纯度: ≥95.0% (UV); ≥98% (EmM/453 = 60); 97%
• 级别: purum
• 燃烧残渣: ≤0.5%
• 简要说明: Isomers; mixed isomers
• Empirical Formula (Hill Notation): C33H36N4O6
• 分类: Rare Genuine Natural Compounds

详细说明

Sigma Aldrich - B4126

Biochem/physiol Actions
It appears to function as an antioxidant and efficient peroxyl radical scavenger, protecting membrane lipids from oxidation by these radicals. At nanomolar concentrations it has been shown to protect neurons from oxidative damage.
Well over 99% of total bilirubin is transported as a conjugate with albumin. Abnormally high levels of bilirubin can cause severe neurological damage, but mildly elevated levels are linked to protection from oxidative stress.
Caution
Protect from light.
Other Notes
A major component of hemoglobin decomposition. The principal pigment of bile, and the yellow color in jaundice.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. B4126.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
包装
1, 5 g in glass bottle

Sigma Aldrich - 14370

Analysis Note
λmax. ～453 nm, mol. absorption >56100 (chloroform)
Application
Bilirubin can be used to study cell biology, bioactive small molecules, biochemicals and reagents, plasma and blood proteins, and proteins and derivatives. Bilirubin-reducing enzymes effectively dispose of electrons produced by fermentolytic processes in the anaerobic bacteria, Pseudomonas dacunhae. Bilirubin has been used in a study to indicate a cytokine link between acute pancreatitis and fibromyalgia, as well as to study hematological abnormalities in hepatitis C virus infection.
Biochem/physiol Actions
Well over 99% of total bilirubin is transported as a conjugate with albumin. Abnormally high levels of bilirubin can cause severe neurological damage, but mildly elevated levels are linked to protection from oxidative stress.