インデカン
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/06/06 11:27:48」(JST)
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Indican
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| Names |
| IUPAC name
(2R,3S,4S,5R,6S)-2- (Hydroxymethyl)-6-(1H-indol -3-yloxy)tetrahydropyran-3,4,5-triol
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| Identifiers |
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CAS Registry Number
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1328-73-0 Y |
| ChemSpider |
390239 N |
InChI
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InChI=1S/C14H17NO6/c16-6-10-11(17)12(18)13(19)14(21-10)20-9-5-15-8-4-2-1-3-7(8)9/h1-5,10-19H,6H2/t10-,11-,12+,13-,14-/m1/s1 N
Key: XVARCVCWNFACQC-RKQHYHRCSA-N N
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InChI=1/C14H17NO6/c16-6-10-11(17)12(18)13(19)14(21-10)20-9-5-15-8-4-2-1-3-7(8)9/h1-5,10-19H,6H2/t10-,11-,12+,13-,14-/m1/s1
Key: XVARCVCWNFACQC-RKQHYHRCBQ
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| Jmol-3D images |
Image |
| PubChem |
441564 |
SMILES
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C1=CC=C2C(=C1)C(=CN2)OC3C(C(C(C(O3)CO)O)O)O
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| Properties |
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Chemical formula
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C14H17NO6 |
| Molar mass |
295.29 g/mol |
| Melting point |
178-180 °C (decomposes) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| N verify (what is: Y/N?) |
| Infobox references |
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Indican is a colourless organic compound, soluble in water, naturally occurring in Indigofera plants. It is a precursor of indigo dye.[1]
Contents
- 1 Chemical reactions
- 2 Medical significance
- 2.1 Biosynthesis
- 2.2 Pathology
- 3 References
Chemical reactions
Common and significant reactions involving indican are as follows:
- Indican is a glycoside. Its hydrolysis yields β-D-glucose and indoxyl.
- Reaction of indoxyl (indican) by a mild oxidizing agent, e.g. atmospheric oxygen, yields indigo dye which is blue in colour.
Medical significance
Biosynthesis
A reaction, similar to the above mentioned is seen in the normal population,[2] who excrete small amounts of the chemical in their urine. Normal urine reacting to hydrogen peroxide does at times produce a bluish tinge. Tryptophan is first converted to indole (excreted in faeces), then to indican by bacteria in the gut. Indican, being water soluble, is then excreted through the urine. Following absorption from the gut, indole is converted to 3-hydroxy indole (indoxyl or indican) in the liver, where it is again then conjugated with sulfuric acid or glucoronic acid through normal xenobiotic metabolism pathways. It is then transported to the kidneys for excretion.[3][4]
The enzyme "indoxyl esterase" has been found in humans and is involved in another pathway of chemical reactions involving indoxyl.[5]
Pathology
In individuals affected by the blue diaper syndrome, the patients exhibit a defect in tryptophan metabolism. and from there into the diaper where, upon exposure to air, it is converted to indigo dye due to oxidation by atmospheric oxygen.
Indican interferes with many commercial procedures for measuring total bilirubin[6] which can be a problem for renal failure patients where blood indican levels are raised. It can cause gastrointestinal symptoms in patients where protein absorption is reduced - like Hartnup's disease, allowing for greater bacterial decomposition of the Tryptophan to indole and its conversion to indican.
References
- ^ Definition: indican from Online Medical Dictionary
- ^ Urinary Excretion of Indoxyl Sulfate (Indican) by Human Subjects Ingesting a Semisynthetic Diet Containing Variable Quantities of l-Tryptophan - BRYAN 19 (2): 113 - American J...
- ^ Urine Indican Test
- ^ Bio Center Lab tests Urine Metabolism - Indican
- ^ http://www.jcb.org/cgi/reprint/39/2/286.pdf
- ^ Indican interference with six commercial procedures for measuring total bilirubin - Poon and Hinberg 31 (1): 92 - Clinical Chemistry
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Glycosides
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| Bond |
- O-glycosidic bond
- N-glycosidic bond
- S-glycosidic bond
- C-glycosidic bond
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| Geometry |
- α-Glycoside
- β-Glycoside
- 1,4-Glycoside
- 1,6-Glycoside
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| Glycone |
- Fructoside
- Galactoside
- Glucoside
- Glucuronide
- Rhamnoside
- Riboside
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| Aglycone |
- Alcoholic glycoside
- Cardiac glycoside
- Bufadienolide
- Cardenolide
- Cyanogenic glycoside
- Glycosylamine
- Phenolic glycoside
- Anthraquinone glycoside
- Coumarin glycoside
- Flavonoid glycoside
- Saponin
- Steviol glycoside
- Thioglycoside
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Index of biochemical families
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| Carbohydrates |
- Alcohols
- Glycoproteins
- Glycosides
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| Lipids |
- Eicosanoids
- Fatty acids
- Glycerides
- Phospholipids
- Sphingolipids
- Steroids
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| Nucleic acids |
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| Proteins |
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| Other |
- Tetrapyrroles
- intermediates
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English Journal
- Adecuación de las peticiones de los niveles de vitamina D al laboratorio.
- Valero Chávez FJ1, Luengo Pérez LM, Cubero Juánez J.
- Nutricion hospitalaria.Nutr Hosp.2016 Sep 20;33(5):581. doi: 10.20960/nh.581.
- Introducción: ante las nuevas implicaciones atribuidas a la vitamina D y la asociación con enfermedades tales como el cáncer, diabetes, enfermedades cardiovasculares, autoinmunes y mortalidad, no es de extrañar que se haya defendido la medición de los niveles de vitamina D en la población gene
- PMID 27759985
- Fatigue in children and adolescents with cancer from the perspective of health professionals.
- Silva MC1, Lopes LC Júnior2, Nascimento LC3, Lima RA4.
- Revista latino-americana de enfermagem.Rev Lat Am Enfermagem.2016 Aug 29;24:e2784. doi: 10.1590/1518-8345.1159.2784.
- OBJECTIVE: to investigate health professionals' knowledge about the concept, assessment and intervention in fatigue in children and adolescents with cancer.METHOD: exploratory study with qualitative approach, with 53 health professionals (10 nurses, 33 assistant nurses, 3 physicians, 3 nutritionists
- PMID 27579937
- Healthy aging profile in octogenarians in Brazil.
- Campos AC1, Ferreira EF2, Vargas AM3, Gonçalves LH4.
- Revista latino-americana de enfermagem.Rev Lat Am Enfermagem.2016 Aug 29;24:e2724. doi: 10.1590/1518-8345.0694.2724.
- OBJECTIVE: to identify the healthy aging profile in octogenarians in Brazil.METHOD: this population-based epidemiological study was conducted using household interviews of 335 octogenarians in a Brazilian municipality. The decision-tree model was used to assess the healthy aging profile in relation
- PMID 27579929
Japanese Journal
- Development of a highly efficient indigo dyeing method using indican with an immobilized β-glucosidase from Aspergillus niger(ENZYMOLOGY, PROTEIN ENGINEERING, AND ENZYME TECHNOLOGY)
- Song Jingyuan,Imanaka Hiroyuki,Imamura Koreyoshi,Kajitani Kouichi,Nakanishi Kazuhiro
- Journal of bioscience and bioengineering 110(3), 281-287, 2010-09
- … In this method, the substrate, indican is first hydrolyzed at an acidic pH of 3 using an immobilized β-glucosidase to produce indoxyl, under which conditions indigo formation is substantially repressed. … As an enzyme, we selected a β-glucosidase from Aspergillus niger, which shows a high hydrolytic activity towards indican and was thermally stable at temperatures up to 50-60℃, in an acidic pH region. …
- NAID 110007730016
- オクタビオ・パスにおける意味の危機に立ち向かう詩--世界のイメージと科学技術を通して
- 高野 雅司
- HISPANICA / HISPÁNICA 2010(54), 103-124, 2010
- … y Renga, no indican una mera vuelta a la poesía del pasado. …
- NAID 130000414726
Related Links
- Indican definition, a glucoside, C 14 H 17 NO 6 , that occurs in plants yielding indigo and from which indigo is obtained. See more. Thesaurus Translate Puzzles & Games Reference Word of the Day Blog Slideshows Apps by ...
- indican /in·di·can/ (in´dĭ-kan) potassium indoxyl sulfate, formed by decomposition of tryptophan in the intestines and excreted in the urine. in·di·can (ĭn′dĭ-kăn′) n. A potassium salt found in sweat and urine and formed by the conversion ...
Related Pictures
★リンクテーブル★
[★]
- 英
- indican
- 同
- 3-インドキシル硫酸
- 関
- オーベルマイヤー法、トリプトファン、インドール、インドキシル
- 生体では、蛋白中のトリプトファンは細菌によってインドールとなり、腸管から吸収、肝臓で参加されインドキシルとなる。さらに硫酸と結合してインジカンとなる。インジカンは解毒され尿より排泄される。尿中に著増する病態は腸内容停滞・以上分解、青いおむつ症候群、Hartnup病などである(LAB.188)